Chappaqua, N.Y.

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The name Chappaqua is derived from an Algonquin word which translates as “running water”. Lakes, ponds and streams are abundant among the rolling wooded hills of Chappaqua. A large portion of the land has been preserved as undeveloped, open space, which helps to create Chappaqua’s rural feeling. With faithful adherence to environmental and architectural review, the town has managed to retain a country feeling with a great deal of privacy for individual homes. Architectural styles range from antique colonials to exquisite contemporaries.

From the Chappaqua train station, New York City’s Grand Central Station is a 50-minute ride. White Plains is only ten minutes away and the Saw Mill River Parkway runs right by town. The great combination of privacy and accessibility makes Chappaqua very attractive for New York City commuters. In 1864, Horace Greeley took up residence in Chappaqua and more recently, former President Bill Clinton and Senator Hillary Clinton made Chappaqua their home. Residents place a high priority on education and the Chappaqua Central School District ranks consistently among New York State’s best schools with Scholastic Aptitude Test scores well exceeding the average.

ACTIVE LISTINGS:

This distinguished 7,300-square-foot Colonial residence, constructed in 2007, is ideally situated on a level, professionally landscaped property, offering a rare blend of timeless architectural elegance and modern luxury. Meticulously designed and impeccably maintained, this exceptional home features four en-suite bedrooms with space for a fifth , a spacious bonus room/office, and a thoughtfully curated layout that strikes a balance between refined entertaining and everyday living. A dramatic two-story foyer introduces sun-drenched interiors adorned with detailed millwork, soaring ceilings, and four fireplaces—two adaptable for wood or gas—enhancing the formal living room, great room, primary suite, and lower-level entertaining space. At the heart of the home is a chef’s kitchen, outfitted with premium stainless steel appliances, custom cabinetry, and a striking marble island. This space opens gracefully to both formal and casual living areas, featuring multiple doors that lead directly to the porch, pool and patios, providing a seamless indoor-outdoor flow—ideal for entertaining, al fresco dining, and effortless serving. The main level is further enhanced by a custom-built mudroom with built-in storage, two elegantly appointed powder rooms, and an ideal layout for both formal and informal occasions. The expansive primary suite offers a private sanctuary, complete with a sunlit sitting room, custom walk-in closet, and a newly renovated spa bath finished with premium materials and fixtures. Three additional en suite bedrooms offer privacy and comfort, while the generously proportioned bonus room provides flexible space for a media lounge, home office, playroom, or guest accommodations. The walk-out lower level enhances the home’s appeal, featuring a full summer kitchen, a state of the art fitness center, a full bath, and an extraordinary 1,400-bottle climate-controlled wine room. A built-in movie screen paired with a state-of-the-art Dolby surround sound system creates a truly immersive in-home theater experience. Direct access to the grounds enhances the home’s indoor-outdoor lifestyle.
The completely private, fully-fenced exterior is equally impressive, with a heated Gunite pool, patio, multiple lounging areas and flat lawns ideal for recreation, and a fully equipped outdoor kitchen designed for exceptional outdoor entertaining. Landscape uplighting and a backyard sound system enhance your outdoor enjoyment. This stately and luxurious residence represents a rare opportunity to acquire a home of scale, quality, and distinction in one of the area’s most sought-after locations.

$3,699,999 Active

5 Briarcliff Road Chappaqua, New York

4 Beds 7 Baths 7,305 SqFt 1.29 Acres

Exceptional and sophisticated Nantucket shingle style Colonial on 3.66 private acres in one of Chappaqua’s most desirable neighborhoods, offers the perfect balance of casual elegance and resort-style living. Just 45 minutes from NYC and minutes to town, train, and top-rated schools, this turnkey home offers unmatched convenience and luxury. Designed for both everyday comfort and effortless entertaining, the property features sophisticated interiors and breathtaking outdoor spaces—creating a true sanctuary for modern family living. From the moment you arrive, you’ll be captivated by the lush, professionally landscaped grounds and impeccable curb appeal. The backyard is a true resort-style retreat, complete with a sparkling pool and spa, a built-in fire pit, an outdoor refrigerator and beverage area, and expansive level lawns—perfect for entertaining or unwinding in total privacy. Step inside and experience a turnkey masterpiece of design and craftsmanship. The interiors are adorned with high-end finishes, custom millwork, gorgeous hardwood floors and designer touches throughout. The chef’s kitchen is an entertainer’s dream, featuring top-of-the-line Wolf ovens and microwave, a six-burner Wolf range, a separate full size Sub-Zero refrigerator and freezer, dual dishwashers, and sleek, custom cabinetry. Other first floor highlights include a large office, a family room w/walls of windows, a billiard or living room w/ bar and sleek built-ins, and an incredible oversized screened porch w/fireplace and TV—perfect for gatherings and seamless indoor-outdoor entertaining. Upstairs, the primary suite is a luxurious sanctuary, boasting exposed wood beams, a cozy stone fireplace, a spa-like ensuite bath w/ steam shower, and generous walk-in closets. Three additional oversized bedrooms—two sharing a bath and one with its own ensuite—offer ample space and comfort, all connected by a versatile upstairs lounge area perfect for homework or hanging out. The finished walkout lower level adds even more living space with a media/playroom, a state-of-the-art home gym, a full bath, and access to a covered porch. Additional premium features include a heated three-car garage, whole-house generator, dual laundry rooms, whole house camera security system, and stunning stone walls that frame the property’s exceptional landscaping. Meticulously maintained and 100% move-in ready, this one-of-a-kind estate is a rare opportunity to enjoy resort-caliber living in a premier location. Prepare to fall in love!

$3,499,000 Active

93 Haights Cross Road Chappaqua, New York

4 Beds 5 Baths 6,542 SqFt 3.66 Acres

Significant price adjustment! Set on a sprawling 4.11-acre parcel in the esteemed Chappaqua enclave, 20 Bessel Lane offers an unparalleled blend of sophisticated living and natural tranquility. Every aspect of this residence and its grounds has been thoughtfully curated to fuse the home's refined design with the property's lush surroundings. The residence, boasting an expansive 7,978 sqft of living space, is designed with attention to detail and functionality. Expansive windows throughout the home frame views of the meticulously landscaped grounds, ensuring a continual connection to nature. Comprising 6 generously proportioned bedrooms and 5.5 bathrooms, this home meets both luxury and daily living needs with finesse. The dedicated home office and a bespoke home gym are significant additions, recognizing contemporary lifestyle requisites. Outdoors, the Shoreline pool is the centerpiece, designed to harmonize with the property's lush backdrop. Adjacent to the pool, a fully-equipped cabana with a kitchen is perfect for effortless entertaining. Tennis aficionados will find the private court, nestled among mature trees and rock formations, an exceptional addition. A unique feature of this estate is its dedicated orchard and vegetable garden area-a nod to sustainable living and a source of organic produce right in your backyard. Comprehensive amenities like a full irrigation system and thoughtful outdoor lighting ensure the grounds remain both functional and picturesque. Chappaqua's reputation for distinguished schools and a vibrant, tight-knit community make it a coveted location. Further enhancing this property's appeal is its proximity to New York City-just a 45-minute train journey, ensuring urban amenities are within easy reach., Additional information: ExterioFeatures:Tennis,Interior Features:Guest Quarters,Lr/Dr,Marble Bath

$3,475,000 Active

20 Bessel Lane Chappaqua, New York

6 Beds 6 Baths 7,978 SqFt

Welcome to 70 Haights Cross, a stunning turn-key 5 bedroom, 7.2 bath colonial designed by noted architect Tasos Kokoris. Located in a coveted neighborhood, this home is set on 2 plus private professionally landscaped acres with a Gunite pool with waterfall and jacuzzi. The heart of the home lies in the gourmet kitchen featuring a Wolf-6-burner range, warming and fridge drawer, 2 Bosch dishwashers and a Subzero refrigerator. Flooded with sun-light and offering all of today's modern amenities, this home is truly a serene oasis offering unparalleled living space and is perfect for indoor or outdoor entertaining with an oversized deck and stunning patio. There is an expansive family room with gas fireplace, a wood paneled library with wood burning stove, home office and upstairs gathering room. The lower level features a spectacular garden room leading to a patio, 2 full baths, rec room, lounge, sitting room and mudroom. This home borders Glazier Arboretum and its spectacular hiking trails for ultimate tranquility: private and serene! Experience the pinnacle of gracious living.

$3,150,000 Active

70 Haights Cross Road Chappaqua, New York

5 Beds 9 Baths 8,775 SqFt 2.17 Acres

Introducing this spectacular country retreat, nestled peacefully on over four and a half acres in the leafy and much loved hamlet of Chappaqua. A glorious heated pool, panoramic patios, and endless lawns for play - offering complete privacy and seclusion, while just minutes from Chappaqua’s vibrant downtown and top-rated schools! At the end of the long scenic drive, an architectural beauty awaits. Inside, a dramatic 2-story foyer flows into a truly magnificent ‘Great Room’ with breathtaking floor-to-ceiling glass windows, a towering stone fireplace and a glass door to the patio and pool. Serene woodland views are all around, from the gym, to the cherry-paneled library, to the gourmet kitchen with Thermador & Sub-Zero appliances, to the chic dining room and sunken living room with covered side patio! This home features 5 beds all ensuite, one which is privately positioned on the 1st floor with a separate entrance. Plus, there’s a mudroom with access to the 3-car garage. On the next level the primary is pure bliss with a sunny balcony, 2 walk-in-closets and ensuite with steam shower and sauna. This floor also boasts a fabulous bonus room with skylights. The lower level offers even more space with a party room, small kitchen and full bath, rec room, craft room and abundant storage. All this, set against a vast, open panorama that celebrates stunning sunsets, just a 45 minute commute to NYC!

$2,950,000 Pending

26 Hemlock Hills Chappaqua, New York

5 Beds 7 Baths 7,038 SqFt 4.79 Acres

Welcome Home to Your Dream Colonial in the Chappaqua School District. Discover luxury and comfort in this sunlit center-hall colonial, boasting over 6,333+ square feet of living space. Set back on 2.25 private, level acres, this home features a fenced-in backyard with a heated saltwater pool, an automatic cover, and expansive patio and deck spaces perfect for entertaining and recreation. Highlights Include: Elegant Curb Appeal: Drive through stone pillars to this amazing property. Exceptional Layout: Five en-suite bedrooms, including a luxurious primary suite with his and hers bathrooms and closets, a first floor bedroom, plus an upstairs den and separate office. Gourmet Kitchen: Custom cabinetry, Sub-Zero refrigerator, Viking stovetop, double wall ovens, Miele built-in coffee machine, and more. Incredible Lower Level: A state-of-the-art cinema room, a 1,200+ bottle wine cellar, and a playroom with access to the side yard. Additional Features: A fabulous home gym, a three-car heated garage with direct mudroom access, and abundant natural light throughout. Entertainer’s Dream: The enclosed sunroom, back patio and deck overlook a sprawling fenced in yard, ideal for gatherings, sports, and poolside relaxation. This home combines elegance, comfort, and practicality, with every space thoughtfully designed for modern living. Don’t miss the opportunity to make this exceptional property your own—schedule your private showing today!

$2,825,000 Pending

66 Kerry Lane Chappaqua, New York

6 Beds 8 Baths 6,333 SqFt 2.25 Acres

Located in the coveted Whippoorwill estate area, 61 Carolyn Place presides on 2.19 manicured acres and overlooks the Whippoorwill Country Club’s private golf course. Meticulous details abound with lofty ceilings and spacious rooms, complemented by warm, inviting, intimate spaces and outdoor areas. An open gourmet kitchen and breakfast room flow to the grand two-story family room and dedicated solarium, both accessing a large outdoor deck and rocking chair porch. The second-floor features a large primary suite with a gorgeous, sun-drenched bedroom complete with western-views and a wood burning fire place. A sitting room/second office, double walk-in closets, and a lavish bath with a jacuzzi tub, dual vanities and a spacious shower complete the suite. A wide hallway spanning the breadth of the home gives access to two additional ensuite bedrooms, the upstairs laundry room, and home office. The home’s eastern wing, features the final two bedrooms, connected by a Jack-and-Jill bath and features a Juliet balcony overlooking the front yard. A heated, three car garage, connecting mudroom, and full, walk-out basement complete the interior, while the expansive front and backyards feature vast rolling lawns, beautiful scenery, and a potential pool site. Conveniently located between Chappaqua and Armonk, close to town and highways, and approximately 50 minutes to NYC, 61 Carolyn Place is a truly remarkable home and not to be missed.

$2,800,000 Active

61 Carolyn Place Chappaqua, New York

5 Beds 6 Baths 5,907 SqFt 2.19 Acres

Welcome to this timeless and sophisticated Colonial, perfectly sited on meticulously landscaped grounds in one of Chappaqua’s most coveted neighborhoods. Just minutes from town, train, and top-rated schools, this exceptional residence seamlessly blends classic architectural charm with modern luxury. This fully renovated and expanded home offers 4 spacious bedrooms (lives like 5), 6.1 beautifully updated baths, and a thoughtfully designed layout filled with natural light. Gleaming hardwood floors, walls of windows, and elegant millwork create a warm and inviting atmosphere throughout. The stunning Chef’s kitchen is a true showpiece, featuring Christopher Peacock custom cabinetry, oversized center island with Carrera marble top, Pietra del Cadoso limestone kitchen countertops, top-of-the-line stainless appliances (Bosch, Thermador, Viking) and an open flow ideal for entertaining.
The main level enjoys multiple formal and informal living spaces including an expansive family room open to the kitchen, a versatile first floor office, a second office/library, full bath and a serene screened sun porch. The second level features a luxurious primary bedroom suite and three additional huge bedrooms, one with an en-suite bath and a hall bath. The walkout lower level adds even more functionality with room for recreation, fitness, or guests. Recent mechanical upgrades include a high efficiency GE front-loading washer and dryer, NEW (May 2025) Energy Kinetics System 2000 High-Efficiency Boiler designed to reduce oil consumption, and above-ground oil tanks, ensuring comfort and efficiency for years to come. The exterior is equally captivating: clapboard siding, a hand split cedar shake roof, copper gutters, bluestone walkways, an expansive rear patio with built-in grill and stone walls, a Mahogany deck, and a manicured, level lawn with vibrant gardens, professional landscaping and an irrigated vegetable garden. Additional highlights include an oversized driveway, a two-car garage, and an adjacent garage bay-sized storage room perfect for bicycles, equipment, or hobbies. A rare offering that effortlessly combines grace, comfort, and convenience — 35 Overlook Drive is an extraordinary opportunity for the discerning buyer.

$2,699,000 Active

35 Overlook Drive Chappaqua, New York

4 Beds 7 Baths 5,354 SqFt 1.22 Acres

Arise to astonishing sunrises in this gorgeous, modern farmhouse privately set on 2.75 estate-like acres at the end of a cul-de-sac in prestigious Lawrence Farms East. Newly rebuilt in 2020 and further refined since. Grand, two-story entry foyer introduces open floor plan for today’s contemporary living style. Inviting living/dining area with large, front-facing windows, wood-burning fireplace, shiplap paneling and beamed ceiling. Epicurean kitchen outfitted with custom cabinetry, Viking stainless-steel appliances, large center island with apron-front farm sink and breakfast bar, and windowed breakfast area with French door to the patio for easy BBQ or alfresco dining. Adjoining the kitchen is the captivating family room, capped by a wood-beamed cathedral ceiling and with an impressive array of large windows overlooking the rear of the property. A powder room for guest refreshment is discreetly tucked in the corner. The recently enclosed (2021) sunroom is an excellent space for yoga, exercise, or quiet reflection. A main-level bedroom, and recently renovated (2024) full bath offer guests private quarters. Completing the main level are the laundry room, and mud room with access to attached, 2-car garage with Tesla charger. The upper-level features four bedrooms, all with hardwood flooring, and three bathrooms, including a new (2024), custom designed primary suite with luxurious, ensuite bathroom and large walk-in closet. The lower-level houses storage, utilities and mechanicals. Outside is an eden itself, being a natural extension of the adjoining Whippoorwill Park, a 220-acre nature preserve. On site, new landscaping (2022), sprinklers (2023) and walkways (2024) enhance the property. An invisible dog fence rings the yard. Lots of lawn for play or relaxation. Within walking distance to Horace Greeley High School, Mount Kisco Country Club, Crabtree’s Kittle House, Chappaqua Crossing with Chappaqua Performing Arts Center, Whole Foods, Lifetime Fitness, sweetgreen, and more, and spectacularly set on a picturesque cul-de-sac in the most sought-after neighborhood.

$2,695,000 Pending

35 Ivy Hill Road Chappaqua, New York

5 Beds 5 Baths 4,004 SqFt 2.75 Acres

Welcome to 92 Random Farms Drive, ideally located in the sought-after Random Farms community of Chappaqua. Completely renovated in 2022, this stunning turnkey residence showcases modern design, luxurious upgrades, and an open layout tailored to today’s lifestyle.
The main level features a dramatic double-height entry foyer, a gourmet kitchen outfitted with premium appliances, a sunlit living room, formal dining room, expansive great room, and a versatile home office. Thoughtful details include two beautifully updated powder rooms and a custom mudroom/laundry area with built-ins. Upstairs, the private primary suite offers a spa-inspired custom bath, complemented by three additional bedrooms and two full bathrooms—one of which is en-suite. The finished lower level adds a full bath, generous storage, and flexible space ideal for recreation, entertaining, or relaxation. Move-in ready and designed for both comfort and style—don’t miss this exceptional opportunity to call Random Farms home.

$2,499,999 Pending

92 Random Farms Drive Chappaqua, New York

4 Beds 6 Baths 5,254 SqFt 1.02 Acres

Introducing a luxurious lifestyle at 8 Turtleback Way in the prestigious Hardscrabble Lake Community of Chappaqua. This private neighborhood graced with delightful lakes is perfect for peaceful strolls and getting in your daily steps. It also offers the convenience of door-to-door school bus service within the top-rated Chappaqua School District. Nestled on a magnificent 1.24-acre lot, this 6,649 square-foot modern Center Hall Colonial spans three full levels, showcases impressive curb appeal, breathtaking views, and ample opportunities for nature watching, gardening, entertaining, and various outdoor activities. A grand Cathedral 2-story entry hall with a dramatic staircase, and an arched window welcomes you into this meticulously maintained home. Enjoy the warmth of a wood-burning fireplace as you enter the formal living room with French doors that lead into a richly appointed wood-paneled office/den, all illuminated by recessed lighting. The warm ambiance of the formal dining room offers a spacious layout and a privacy door to the butler's pantry. At the heart of the home lies the gourmet chef's eat-in kitchen with a generous center-island for gatherings, a conveniently located pantry room, a built-in desk, and a charming breakfast area. The kitchen effortlessly flows into the bright family room, featuring sliders that open to an expansive deck ideal for BBQs, al fresco dining, and enjoying the sprawling grounds. The guest powder room was placed for easy access. Upstairs, you will discover the primary bedroom is complete with its luxurious en-suite marble bath, two vanities, radiant heated floor, a walk-in closet, and custom wall built-in. There are two hall bathrooms upstairs to which all four additional bedrooms have access. As a unique bonus, the walkout 2,103 sqare-foot lower level adds two more bedrooms, making a total of seven bedrooms in this exceptional home and further complemented by another full bath, a spacious recreation/media room, a gym, a private laundry room, two cedar closets, and a large storage room. The professionally landscaped property is truly a private oasis and offers the potential for a pool. Additional special features include a spacious 3-car garage with more storage, a whole-house generator, an indoor/outdoor sound system, a security system, a central vacuum system, and a full exterior irrigation system. This exceptional home at 8 Turtleback Way offers an unparalleled lifestyle in one of Chappaqua's finest communities.

$2,485,000 Pending

8 Turtleback Way Chappaqua, New York

5 Beds 5 Baths 6,649 SqFt 1.24 Acres

Turn-key, custom-built 5-bedroom center-hall colonial in Chappaqua’s desirable Hardscrabble Lake community. First floor includes an open floor plan between the updated kitchen and family room with wood-burning fireplace and sliders to the oversized, new Trex deck, a large living room with french doors to the library with access to the deck, formal dining room, powder room, mudroom and door to the heated and air-conditioned 3-car garage. The top floor includes a primary bedroom suite with 2 walk-in closets, sun-filled primary bathroom with two separate vanities, walk-in steam shower and free standing soaking tub. Adjacent to the primary suite is a cozy study, 2 ensuite bedrooms with full bathrooms and one with access to the hall, plus a large fourth bedroom with walk-in closet and a 2nd floor laundry room. Completing this incredible home is a full walk-out lower level features a large rec room/family room with dry bar, wine cellar, a home theater, gym, full bathroom, and a bedroom/office. Enjoy entertaining and relaxing on the spacious, new Trex deck, play in the yard or telling stories while roasting marshmallows around the firepit. This property provides plenty of privacy with stone pillars at the entrance of the tree-lined driveway leading to the house. All just minutes to the town of Chappauqua and Metro North Train station into Grand Central Station.

$2,300,000 Active

3 Boulder Trail Chappaqua, New York

5 Beds 5 Baths 5,183 SqFt 1.11 Acres

Spectacular 5-bedroom, 4 1/2 bath, 6,495 sq ft Colonial, located in the sought after Hardscrabble Lake neighborhood within the renowned Chappaqua School District. This home features a spacious, sun drenched open floor plan accented by large rooms, high ceilings, refined hardwood floors, walls of windows, and exquisite detailing throughout. As one enters, the expansive cathedral ceiling front foyer, they are introduced to the inviting spaces within this home. At the center of this elegant home is a substantial chef's kitchen, flooded with natural light, with breakfast area, top-of-the-line stainless steel appliances, an oversized center island, desk area, and custom white wood cabinetry. The kitchen opens to a vast bluestone patio and rear yard making it perfect for seamless indoor-outdoor living. This special home transitions seamlessly between formal and casual living spaces, ensuring comfort and luxury in every corner. The home offers a substantial 2,105 sq ft walkout finished lower-level, which includes a fitness room, billiard room, and additional entertainment areas, complemented by a full bath. The home's private backyard is an idyllic retreat featuring meticulous perennial gardens, intricate stonework, and level play areas with probable pool site, ideal for outdoor gatherings. Storage is plentiful throughout the home, from walk-in closets to designated spaces. Spacious 3-car garage w/built in cabinetry for ample parking, private laundry room, whole house generator, whole house surround sound system, high pressure booster water system, full exterior irrigation system, outdoor lighting, and more. A must see!!

$2,249,000 Pending

11 Boulder Trail Chappaqua, New York

5 Beds 5 Baths 6,495 SqFt 0.93 Acres

REINTRODUCING 50 Overlook Drive, an elegant 6-bedroom colonial Tudor set in a quiet, tree-lined neighborhood. With fresh upgrades completed this month, including interior repainting, carpet-removal to expose wood floors, and beautiful staging, this one-of-a-kind home is a must see.

Meticulously maintained heating and cooling systems, brick exterior, and a classic-tile roof are some of the exceptional features this home can offer. Homes built to this quality are a rare find! Constructed in 1929, the home is also graced with soaring ceilings, intricate period moldings, and expansive sunlit interiors.

Designed for both grand entertaining and comfortable living, this spacious home is roaring with charm and can suit a variety of tastes and living styles. The first floor offers a living room with fireplace, an all seasons sunroom, a bright and airy dining room, a kitchen with pantry and wet-bar, a half bath, and an in-law or au pair suite with a full bath. Upstairs features 5 bedrooms and 3 full baths, a grand hallway, and attic access. Additional recreational space is provided in the finished basement, with a family room, a gym, and large mudroom, a half-bath, and a utility room.

The beautifully landscaped 1.2-acre lot boasts stunning specimen plantings and a private stone patio adjacent to the all-seasons sunroom. There is also a charming bridge, designed by renowned architect Ned Baldwin, leading to a park-like setting in the backyard.

This is an incredible opportunity to own a truly distinguished home in one of Chappaqua’s most desirable neighborhoods. Experience the perfect balance of classic architecture and modern luxury in this extraordinary residence, in a home that is built to stand the test of time.

$2,225,000 Coming Soon

50 Overlook Drive Chappaqua, New York

6 Beds 6 Baths 5,234 SqFt 1.2 Acres

Welcome to 56 Annandale Road – a sleek & sophisticated Contemporary Colonial tucked into the prestigious Lawrence Farms East enclave, with panoramic views of the Mount Kisco Country Club’s fairways & pool. This rare offering delivers a perfect blend of privacy, style, & convenience in one of Westchester’s most sought-after communities. Set on almost an acre & a half of beautifully landscaped property, this home offers a fresh take on timeless living. Step through the entry door flanked by beautiful stonework into a large, open foyer & immediately feel the airiness & flow that define the home’s design. Large windows, wide hallways, & seamless transitions between rooms make every space feel connected, yet distinct. The main floor is designed for modern living – spacious enough to entertain, yet warm enough to feel like home. The formal Living & Dining Rooms are framed by elegant fireplaces & oversized picture windows, bringing in natural light & picturesque views. At the center of it all, the chef’s kitchen stuns with custom cabinetry, granite countertops, a large island, a gas cooktop, & high-end appliances from Sub-Zero, Bosch, & Thermador – the ideal space to cook, gather, & connect. With four bedrooms (lives like five), the layout fits today’s needs for flexible, functional spaces. The first-floor primary suite is a serene retreat, complete with its own sitting area & a steam shower in the primary bathroom. A second en-suite bedroom on the main level is perfect for guests, family, or a private office. A huge main level bonus room adds even more versatility – use your imagination. Three french doors give access from the main level to outdoor patio spaces, including one from the Primary Bedroom. A 2nd entrance into a well appointed mudroom & a powder room off the kitchen complete the main level. Upstairs, two additional bedrooms share a Jack & Jill bath & are joined by another spacious bonus room – ideal as a playroom, creative workspace, or remote office. Be sure to check out the extra finished storage space & secret room. The fully finished lower level offers endless options: a fitness zone, home theater, guest suite, storage areas, or all of the above – plus a full bathroom & direct access to the oversized 3-car garage with a Chargepoint EV charger. High-end touches elevate every corner: wide-plank Brazilian Cherry floors, detailed millwork, recessed lighting, a whole-house sound system, & smart upgrades throughout. Outside, enjoy two sun-soaked patios, a built-in propane grill with granite countertops, & a resistance spa/pool that transforms your backyard into a wellness retreat. Other highlights include: automatic whole-house generator (propane), central vacuum, security system, & school bus pickup right at your door. You're just minutes from Chappaqua Crossing’s shopping & dining scene – including Whole Foods, Starbucks, & more – & close to schools, Metro-North, & charming local villages. 56 Annandale Road is more than just a home – it’s where modern luxury meets laid-back elegance. Come experience the best of country club living with a modern twist. This one won’t stay on the market for long.

$2,149,000 Active

56 Annandale Road Chappaqua, New York

4 Beds 5 Baths 4,543 SqFt 1.4 Acres

$1,999,999 Pending

97 Random Farms Drive Chappaqua, New York

4 Beds 4 Baths 4,807 SqFt 1.75 Acres

Nestled on a coveted lane in Chappaqua, this expanded 4-bedroom Colonial offers an unparalleled blend of privacy, luxury, and charm. Set on over 2 acres of meticulously landscaped grounds, this exceptional property features a stunning gunite heated saltwater pool, lush mature plantings, and a picture-perfect setting that defines upscale suburban living. Step inside to discover a beautifully renovated kitchen, outfitted with top-of-the-line Wolf and Sub-Zero appliances, custom cabinetry, and a breathtaking picture window that overlooks the expansive backyard—a true centerpiece of the home. Enjoy family time in the casual family room or cozy nights by the fireplace in the living room. A perfectly situated main-level office is thoughtfully tucked away for quiet and privacy. Upstairs, the primary suite offers a walk-in closet that will delight even the most dedicated shoppers. Whether hosting poolside gatherings or enjoying peaceful mornings in your private sanctuary, this home offers it all.

$1,890,000 Active

50 Kerry Lane Chappaqua, New York

4 Beds 5 Baths 4,051 SqFt 2.02 Acres

Set on 1.04 level acres of beautifully landscaped property with vibrant perennial gardens and mature plantings, this impeccably renovated four-bedroom, three-and-a-half-bathroom Center Hall Colonial offers 4,199 square feet of thoughtfully designed living space in one of Chappaqua’s most sought-after neighborhoods. A gracious foyer with a classic sweeping staircase welcomes you into the home. Just off the entry, you’ll find a private office—perfect for working from home—as well as a stylish powder room. The expansive Great Room combines living and dining into one open, light-filled space, featuring a wood-burning fireplace and French doors that open to a large stone patio ideal for hosting family gatherings or enjoying tranquil afternoons outdoors. The sunny family room is perfect for everyday living, with its cozy fireplace, custom built-ins, and triple exposures overlooking the lush, level yard. Additionally, a discreet, retractable movie screen and projector descend at the touch of button, purpose built for shared family movie nights. The beautifully renovated dine-in kitchen is both warm and functional, with a walnut-topped island, casual dining area, stylish butler’s pantry and generous walk-in pantry. A charming garden room opens directly to the yard, providing another connection between indoor and outdoor spaces. The main level is completed by a play area, mudroom, and convenient laundry with double washers and dryers designed with busy households in mind. The attached two-car garage features an additional half bay for bikes, sports gear, or extra storage, with its own driveway access for added convenience. Upstairs, the tranquil primary suite is a retreat in itself, with custom built-ins, separate his and hers closets, and a luxurious spa bath. Two additional bedrooms and a full hall bath are accessed via the main staircase, while the fourth bedroom, another full bath, and a generous bonus/multipurpose room are reached by a second staircase or through Bedroom 3. The bonus space—perfect for a teen hangout, homework zone, or home gym—includes a balcony overlooking the parklike backyard. Located just minutes from the Chappaqua Swim and Tennis Club and only a seven-minute drive to the charming Village of Chappaqua—with its train station, shops, restaurants, library, and top-rated schools—this exceptional home blends timeless architecture, modern convenience, and family-friendly living in an unbeatable setting. A true Chappaqua gem!

$1,875,000 Pending

55 Deepwood Drive Chappaqua, New York

4 Beds 4 Baths 4,199 SqFt 1.04 Acres

Custom design your dream home in a seamless process with ZappiCo, Westchester County's premier Real Estate Developer! This luxurious home is to-be-built in the highly desirable Chappaqua school district. With 4 spacious bedrooms and 2.5 beautifully appointed bathrooms, this home will be meticulously crafted with the finest materials and attention to detail. As you enter, you will be greeted by an open concept living and dining area, perfect for entertaining guests or relaxing with loved ones. The gourmet kitchen will feature an open layout with granite countertops and semi-custom cabinetry. The open concept main level will also offer a family room & living room - perfect for those who work from home or need a quiet space to study. Upstairs, you will find a spacious master suite complete with a spa-like en suite bathroom and walk-in closet, as well as three additional bedrooms with ample closet space. Other features of this home will include hardwood flooring throughout, energy efficient windows, 2-zone central air, and a finished basement ready for your enjoyment! Outside, landscaping is included to create your own oasis. Level lot set back from the street offers added privacy. Located just a short distance from local restaurants, shops, and parks, this home offers the perfect blend of luxury living and convenience. With the ability to customize your finishes and personal touches, this to-be-built home is the perfect opportunity to create your dream home in Chappaqua. Photos are representative of previously built/sample home and may show options not included in the Elite Spec package.
Other home layouts & sizes can be built on this lot as well.

$1,849,999 Active

00 Gray Rock Lane Chappaqua, New York

4 Beds 3 Baths 4,500 SqFt 0.97 Acres

HOME IS TO BE BUILT. 2 BR very popular Greeley Floorplan with primary on first floor. We have a model of this home to walk through. It is ideally sized at 3,269 sq. ft. and includes 2 BR + office, huge loft, finished basement with media room and full bath. The 2-story open concept great room and kitchen allow for large family gatherings. The open island with ample seating beckons your inner chief to come alive. A private rooftop terrace with outdoor kitchen and grill, 2- car garage and the highest quality interior appointments you've come to expect from Toll Brothers! Once completed this 91 Townhome community will surround it's owners with a delightful and eminently walkable village full of the niceties that make Westchester living so extraordinary; such as charming cafes, fitness center, golf, shuttle to train into Manhattan, walking trails, pool, clubhouse, and much more! Still time to add your own personal touches in both structural and design. Additional Information: ParkingFeatures:2 Car Attached,

$1,807,995 Pending

2 Carriage Lane 81 Chappaqua, New York

2 Beds 4 Baths 3,269 SqFt

Tucked away in a 3+ acre private storybook setting, this reimagined farmhouse blends timeless charm with modern comfort. Set back from the road on a scenic, private property with gorgeous mature landscaping, two tranquil ponds, and wide-open views, this 4-bedroom home is a peaceful retreat unlike any other.
Inside, the open, sunlit layout features oversized windows that invite the outdoors in, and wide-plank hardwood floors that bring warmth to every room. The beautifully updated kitchen anchors the main living space, offering high-end finishes and a seamless flow into dining and gathering areas—perfect for entertaining or quiet nights at home.
Upstairs, the serene primary suite features a spa-inspired bath and a large, hotel-style walk-in closet. Three additional bedrooms and a dedicated office provide ample space for family, guests, or working from home.
A detached garage with finished space above offers endless potential—think studio, gym, office, playroom or guest suite. Whether relaxing on the patio, strolling around the ponds, or enjoying the sweeping grounds, this rare farmhouse property delivers privacy, beauty, and a sense of home that feels like a hidden gem.

$1,799,999 Active

200 Millwood Road Chappaqua, New York

4 Beds 3 Baths 3,009 SqFt 3 Acres

Welcome to this spacious 5 Bedrm Colonial on 1.5+ acres in the sought-after Hardscrabble Lake neighborhood. Step inside and you will be delighted throughout -- by the sweeping double staircase, beautiful light Oak flooring, freshly painted interior and so much more. The formal Dining Room and Living Room/Office are graciously-sized, perfect for entertaining. At the heart of the home is an oversized eat-in Kitchen w/Thermador oven/range, stainless steel appliances, granite countertops and island peninsula that opens to the Family Room with double-sided fireplace and sliding glass doors to the sprawling back deck. A Mudroom, 1st floor Laundry and Butlers Pantry finish off the main floor. Upstairs you will find a Primary Bedroom with walk-in closets and ensuite Bath. Three generously-proportioned Bedrooms and a Hall Bath complete the upstairs. The finished Lower Level is wonderful additional space -- including a Play/Gaming Area with walk-out to side yard, Bedroom, Full Bath, Mechanical Room and Storage. Whole house Generator, central vacuum. This home has it all.

$1,799,000 Pending

101 Hardscrabble Lake Drive Chappaqua, New York

5 Beds 4 Baths 4,930 SqFt 1.51 Acres

Welcome to this meticulously maintained home nestled in the heart of Hillholme, an idyllic and sought after neighborhood minutes to Chappaqua town, train and schools. Thoughtfully expanded by noted architect Carol Kurth, this spectacular three bedroom home (lives like a five bedroom), exudes timeless elegance with superior quality throughout. The first floor boasts an expanded foyer, formal living room with a wood burning fireplace, a formal dining room, a spacious home office with custom cherry wood cabinetry and a first floor primary suite complete with two walk-in closets, a sitting area, and a luxurious spa bath with a heated floor - designed for ultimate relaxation and comfort. At the center of this elegant home is a substantial chef's kitchen, flooded with natural light, top-of-the-line stainless steel appliances, custom white wood cabinetry, a breakfast/eat-in nook, an oversized center island and a cozy seating area making it ideal for both daily living and sophisticated entertaining. The kitchen opens to the family room anchored by a brick fireplace, high beamed ceiling and a heated floor - sure to please the most discerning buyers. Upstairs you will find spacious bedrooms all with ample storage and a fully renovated hall bathroom with a heated floor, double sinks and elegant mirrors with concealed storage. The finished walk out lower level offers valuable additional living space including a practical mudroom, a large recreation room with extensive built-ins and a separate tv viewing area (perfect for play exercise, and work), a bonus room, a full bath and a beautiful laundry room with abundant storage. Spacious heated three-car garage with a dual two-car EV fast charger, full house generator, surround sound system, Ring cameras, high pressure booster water system, and more. The neighborhood is simply wonderful, offering a great sense of community - a special offering not to be missed!

$1,799,000 Pending

1 West Place Chappaqua, New York

3 Beds 4 Baths 3,176 SqFt 0.5 Acres

Featured in Westchester magazine’s “Best Places to Live 2016” as an outstanding example of a Federal style colonial residence, this one-of-a-kind classic offers architectural integrity combined w impeccable present day renovations & amenities. This 5BR/3.1Bth colonial offers center hall layout, multiple fireplaces, exposed hand hewn beamed ceilings, post & beam construction in upper level, wide plank pine floors, extensive millwork & built-ins, renovated EIK, spa style primary en-suite, hall & guest baths. Many windows & soaring ceilings, as well as Fr Drs to a wrap-around porch & patio provide integration of interior & outdoor spaces. Spaciousness & privacy, gracious entertaining rms. The 2 story Fam Rm opens directly to the kitchen & is a “wow”. World class gardens, pond, putting green, children's play area, firepit &stone walls abut Pruyn Audubon sanctuary. This residence is close to all, train/shops/schools/recreation yet offers the ambiance of a vacation home tucked away in an idyllic country setting. Property has proposed pool/garage site. Extraordinary charm, compelling curb appeal, immaculate condition, a unique offering.

$1,799,000 Pending

42 Seven Bridges Road Chappaqua, New York

5 Beds 4 Baths 4,561 SqFt 2.1 Acres

Better than new at Chappaqua Crossings Carriages! Be among the first to experience this spectacular new community featuring a delightful and charming village atmosphere in the heart of Westchester, Chappaqua, NY. This stunning “Byram Newhaven model” situated in a prime location within the community, offers great curb appeal with its expansive front porch, stone walls and specimen plantings; and the distinct advantage of being within walking distance of various conveniences, retail establishments, Life Time fitness center, Starbucks, Whole Foods, community pool & state-of-the art clubhouse, shuttle service to the train for easy access to Manhattan, scenic walking trails, golf nearby and all the lower Hudson Valley has to offer. This exceptional home features beautifully appointed living space of the highest quality and perfectly designed for your enjoyment. It features three bedrooms, three and a half baths, a dedicated main floor office space, a versatile loft, and a large finished lower level complete with a full bathroom and large storage area ready to be finished to create even more space. The open-concept great room and kitchen are conducive to hosting large gatherings, and the expansive island with ample seating will be particularly appealing to those who enjoy culinary pursuits. The inviting fireplace surrounded by custom built-ins enhances the warmth and character of this fabulous room. There is also an ample sized mudroom with custom built-ins, conveniently located off the kitchen and leading to the convenient 2-car garage. This amazing home has been built with the highest quality interior and exterior architectural details with luxury landscape design and amenities surrounding. Also included in the sale are the Tv's, high end whole house surround sound system and terrace furniture. Don't miss the opportunity to call this home your own!

$1,790,000 Active

21 Wallace Way Chappaqua, New York

3 Beds 4 Baths 3,614 SqFt 0.07 Acres

HOME NOT COMPLETED YET- 3 BR Millwood Elite home.
This outstanding home is located in the heart of the neighborhood where you can walk to shopping, cafe, gym, pool and more. Includes 3 BR + 2 offices, loft and outdoor terrace w built in grill and linear fireplace and interior wet bar in loft. The open concept great room and kitchen allow for large family gatherings. The open island with ample seating beckons your inner chief to come alive. A roaring fireplace will warm the entire home. A private rooftop terrace, 2- car garage and the highest quality interior appointments you've come to expect from Toll Brothers round out this spectacular residence! Once completed this 91- Townhome community will surround it's owners with a delightful and eminently walkable village full of the niceties that make Westchester living so extraordinary; such as charming cafes, fitness center, golf, shuttle to train into Manhattan, walking trails, pool, clubhouse, and much more! Additional Information: ParkingFeatures:2 Car Attached,

$1,750,995 Pending

18 Dewitt Drive 71 Chappaqua, New York

3 Beds 4 Baths 3,335 SqFt

Beautiful views welcome you to this updated 5 bedroom Colonial, professionally landscaped and located on a perfect cul de sac close to town and schools! The first floor boasts a gracious formal living room w/ a wood-burning fireplace and formal dining rm featuring a sunny bay window. Chef's eat in kitchen with granite counters, island with seating and sliding glass doors to the deck. The convenient mudroom/ laundry room leads to the oversized 2 car garage. The second floor comprises 5 bedrooms including a splendid primary suite with luxurious en suite bath; one large bedroom with an en-suite bath. 3 additional bedrooms and a stylish hall bath complete the second level. The walk out lower level features a spacious recreation room with a large picture window, bar, office / guest room and built in cabinets perfect for play, exercise or work from home; full bathroom and large storage area complete the lower level. Relax on the expansive deck that overlooks the bucolic property with mature specimen plantings and enjoy the stunning sunrise views! Hardwood floors throughout main levels. Prime, sought after location, near schools, library, Metro-North train station, shops, restaurants, and more. A special offering not to be missed! Award-winning Chappaqua Schools. Sure to please the most discerning buyers!

$1,750,000 Pending

22 Mountain Peak Road Chappaqua, New York

5 Beds 5 Baths 4,419 SqFt 1.18 Acres

FULLY DECORATED AND FURNISHED MODEL HOME FOR SALE. 3432’ ‘Square Feet, 2 BR Byram Farmhouse. This model home includes an array of Luxury upgrades, which you can enjoy and move into this school year (Fall 2025). The Byram includes a finished basement with half bath and many more luxurious finishes. The open concept great room and kitchen allow for large family gatherings. The open island with ample seating beckons your inner chief to come alive. A roaring fireplace will warm the entire home. A private Rooftop Terrace with included Outdoor gas fireplace, 2 - Car Garage and the highest quality interior appointments you've come to expect from Toll Brothers round out this spectacular residence! Once completed this 91- Townhome community will surround it's owners with a delightful and eminently walkable Village full of the niceties that make Westchester living so extraordinary; charming Cafes & Restaurants, Lifetime fitness center, golf, Whole Foods Market, Shuttle to train into Manhattan, Walking Trails, Outdoor Pool, Clubhouse which will open this Summer, and much more.

$1,724,995 Active

19 Wallace Way 25 Chappaqua, New York

2 Beds 4 Baths 3,432 SqFt 0.07 Acres

Ideally located in the coveted Dodge Farms neighborhood, this classic Colonial offers an exceptional combination of space, charm, and functionality. Set on over 1.2 acres of lush, private property, this six-bedroom, 3.5-bath home is perfect for both everyday living and effortless entertaining. Step inside to find a sun-drenched main level featuring a spacious formal living room with a beautiful beamed ceiling, an elegant dining room, and an inviting family room with custom built-ins—ideal for relaxed living and stylish organization. The updated eat-in kitchen boasts high-end stainless steel appliances, granite countertops, and ample cabinetry, with direct access to a stone patio—perfect for outdoor dining and entertaining. Upstairs, the bright and airy primary suite offers a peaceful retreat, complete with custom built-ins, plenty of closet space, and a private en-suite bath. Five additional bedrooms provide plenty of space for family, guests, or flexible use as home offices, gym, or a playroom. Outside, enjoy serene views, mature plantings, and a peaceful setting, all just minutes from the vibrant shops, dining, and train station of downtown Chappaqua.

$1,699,999 Pending

122 Valley View Road Chappaqua, New York

6 Beds 4 Baths 3,939 SqFt 1.22 Acres

Home Under construction a spacious 3269’ ! Move-in by Summer 2025' As you enter the Greeley Newhaven, the exquisite foyer presents sweeping views of this home's open-concept floor plan and luxurious finishes. The spacious kitchen and great room provide the ideal space for entertaining. The casual dining area provides the perfect space for entertaining guests with easy access to the kitchen. The two-story great room is the perfect setting for relaxation with its cozy fireplace and ample natural light. The first-floor primary bedroom suite features a lavish bathroom and a huge walk-in closet. The secondary bedroom includes a shared hall bath. The versatile loft can be suited to fit your lifestyle. Home features a covered and open 2nd floor terrace with built-in outdoor kitchen and gas grill. Work from home in the secluded second-floor office -Enjoy seamless indoor/outdoor living with the large second-floor terrace complete with an outdoor kitchen -The finished basement includes a media room and full bath -This home is located on a private street with wooded views from the terrace and sunset views from your front door.

$1,699,000 Active

8 Carriage Lane 84 Chappaqua, New York

2 Beds 4 Baths 3,269 SqFt 0.08 Acres

Under Construction- Summer 2025 Move-in. 3614 square feet ! Designer features already selected. Home includes a finished basement with full bath, media room and many more upgrades. The open concept great room and kitchen allow for large family gatherings. The open island with ample seating beckons your inner chief to come alive. A roaring fireplace will warm the entire home. A private rooftop terrace with private views , 2- car garage and the highest quality interior appointments you've come to expect from Toll Brothers round out this spectacular residence! Once completed this 91- Townhome community will surround it's owners with a delightful and eminently walkable village full of the niceties that make Westchester living so extraordinary; such as charming cafes, fitness center, golf, shuttle to train into Manhattan, walking trails, pool, clubhouse, and much more! Great room and casual dining area with rear yard access are convenient to the kitchen, ideal for entertaining. Finished lower level features a media room and a full bathroom, providing additional living space. Versatile loft with an additional office can be suited to fit your lifestyle. Large outdoor terrace provides seamless indoor/outdoor living space.

$1,689,995 Pending

4 Carriage Lane 82 Chappaqua, New York

2 Beds 4 Baths 3,614 SqFt 0.06 Acres

Home Under construction! Move-in by Summer 2025' 3269 square feet ! As you enter the Greeley Newhaven, the exquisite foyer presents sweeping views of this home's open-concept floor plan and luxurious finishes. The spacious kitchen and great room provide the ideal space for entertaining. The casual dining area provides the perfect space for entertaining guests with easy access to the kitchen. The two-story great room is the perfect setting for relaxation with its cozy fireplace and ample natural light. The first-floor primary bedroom suite features a lavish bathroom and a huge walk-in closet. The secondary bedroom includes a shared hall bath. The versatile loft can be suited to fit your lifestyle. Home features a covered and open 2nd floor terrace with built-in outdoor kitchen and gas grill. Work from home in the secluded second-floor office -Enjoy seamless indoor/outdoor living with the large second-floor terrace complete with an outdoor kitchen -The finished basement includes a media room and full bath -This home is located on a private street with wooded views from the terrace and sunset views from your front door.

$1,679,000 Active

10 Carriage Lane 85 Chappaqua, New York

2 Beds 4 Baths 3,269 SqFt 0.08 Acres

To be Built! Spring 2025 move-in. 3485 square feet ! Still time to personalize interior finishes at our luxury Design Studio. Final building for sale at Chappaqua Crossing! A roaring fireplace will warm the entire home. A private rooftop terrace with included outdoor gas fireplace, 2- car garage and the highest quality interior appointments you've come to expect from Toll Brothers round out this spectacular residence! The exquisite foyer presents sweeping views of this home's open-concept floor plan and luxurious finishes. Overlooking the great room and accompanied by a casual dining area, the gorgeous kitchen is the perfect environment for entertaining guests with wraparound counter space and a sprawling central island. The spacious primary bedroom suite offers a luxurious bath and impressive closet space. The private workspace on the second floor is the perfect spot to work from home. Once completed this 91- Townhome community will surround it's owners with a delightful and eminently walkable village full of the niceties that make Westchester living so extraordinary; such as charming cafes, fitness center, golf, shuttle to train into Manhattan, walking trails, outdoor pool, clubhouse which will open this Spring, and much more.

$1,658,995 Pending

11 Wallace Way 18 Chappaqua, New York

2 Beds 4 Baths 3,353 SqFt 0.08 Acres

New Construction! Move in Summer 2025! Greeley Floorplan with primary on first floor. It is ideally sized at 3,269 sq. ft. and includes 2 BR + office, huge loft, finished basement with media room and full bath. The 2-story open concept great room and kitchen allow for large family gatherings. The open island with ample seating beckons your inner chief to come alive. A private rooftop terrace with outdoor kitchen and grill, 2- car garage and the highest quality interior appointments you've come to expect from Toll Brothers! Once completed this 91 Townhome community will surround it's owners with a delightful and eminently walkable village full of the niceties that make Westchester living so extraordinary; such as charming cafes, fitness center, golf, shuttle to train into Manhattan, walking trails, pool, clubhouse, and much more!

$1,629,995 Pending

16 Dewitt Drive 70 Chappaqua, New York

2 Beds 4 Baths 3,269 SqFt

As you enter this END UNIT Millwood Elite Fairview, the exquisite foyer presents sweeping views of this home's open-concept floor plan and luxurious finishes. A large center island in the kitchen overlooks the casual dining area. The great room is the perfect setting for relaxation with its cozy fireplace and ample natural light. The appealing primary bedroom suite boasts a lavish bath and ample closet space. Second-floor sitting area w wet bar and refrigerator ,Convenient Laundry room on Bedroom level. Spacious outdoor Terrace with Outdoor Kitchen including Barbecue & Refrigerator. Finished Lower Level with Media room, Full Bath and tons of Storage. Two car Garage. Community is situated just steps away from shopping, dining, and entertainment. Residents Community Clubhouse coming soon. Jitney to Metro North train station. Chappaqua Schools.

$1,624,995 Pending

6 Dewitt Drive 65 Chappaqua, New York

2 Beds 4 Baths 3,353 SqFt 0.09 Acres

TO BE BUILT. Move-in Spring 2026. Spacious 3485 square feet ! Still time to personalize interior finishes by visiting our luxurious Design Studio. As you enter the Millwood Elite, the exquisite foyer presents sweeping views of this home's open-concept floor plan and luxurious finishes. A large center island in the kitchen overlooks the casual dining area. The great room is the perfect setting for relaxation with its cozy fireplace and ample natural light. The appealing primary bedroom suite boasts a lavish bath and ample closet space. The second-floor loft offers endless opportunities for a flexible space. The community is situated just minutes away from shopping, dining, and entertainment. Expand your living space onto the outdoor terrace, complete with an outdoor kitchen and built-in grill.

$1,599,995 Pending

15 Wallace Way 20 Chappaqua, New York

3 Beds 4 Baths 3,353 SqFt 0.08 Acres

$1,599,000 Active

106 Random Farms Drive Chappaqua, New York

5 Beds 4 Baths 3,859 SqFt 0.89 Acres

Welcome to your beautifully maintained 4-bedroom Colonial at 3 Sunset Drive in the heart of Chappaqua! This charming home boasts 3.5 bathrooms and offers a spacious 3,587 square feet of living space. Step inside to find oak wood flooring throughout and a wood-paneled home office, perfect for working from home. Large windows fill the space with natural light, creating a warm and inviting atmosphere. The Second floor features a gracious hallway with four spacious bedrooms with large closets. The fourth bedroom features a private ensuite bathroom, ideal for guests. Enjoy a cozy screen porch, playroom, tons of storage and a freshly painted interior and exterior. The property sits on a generous 1.1 acre lot, will lush lawns, private outdoor patio, and a 2 car garage. Conveniently located , this home is ready to welcome its new owners!

$1,599,000 Pending

3 Sunset Drive Chappaqua, New York

4 Beds 4 Baths 3,587 SqFt 1.11 Acres

Welcome to 58 Spring Lane – A stunning chalet-style retreat nestled at the end of a private lane just a short walk from the town of Chappaqua and Metro North train. This special home exudes timeless elegance and abundant period charm with its cathedral-vaulted ceilings, original gothic doors, expansive windows and versatile entertaining spaces. The main floor primary suite is a true sanctuary – like waking up in a forest canopy – and features an adjoining room with pocket doors ideal for a home office, nursery, or sitting area. Upstairs, three additional spacious bedrooms and full bath are complemented by a delightful nook, perfect for storage or a whimsical playroom. Abundant, well-outfitted closet spaces are found throughout the home. Entertain with ease in the beautifully updated kitchen with custom cabinetry and high-end appliances, all encompassing sleek finishes that blend modern appeal with classic charm. Be sure to check out the full-closet revolving spice rack. Powder room located conveniently off the kitchen adjacent the front door. An oversized dining area off the kitchen offers a gas fireplace and expansive views to the backyard with amazing natural light. Enjoy cozy evenings and effortless entertaining options in the cathedral-like living room with palladian-style windows and direct access to an outdoor wrap-around stone terrace – perfect for hosting meals and watching sunrise/sunset. Other highlights of the home include an outfitted workshop (formerly garage) with built-in shelving and side entry, and a finished walk-out lower level with a wet bar offering multiple options for a gym, playroom, or home office. Stone terraces and a wooden deck with views of the backyard offer ample entertaining options. Comfort and sustainability abounds with the home's 10.6KW solar panel array and Unico small-duct, high-velocity central heating, ventilation and air conditioning technology. This private oasis with gated-entry borders preserved land with direct access to a private trail leading to Pinecliff Audubon Sanctuary. Walking distance to town and train. A truly one-of-a-kind offering that is not to be missed.

$1,575,000 Active

58 Spring Lane Chappaqua, New York

4 Beds 3 Baths 3,457 SqFt 2 Acres

Beautiful, spacious, completely renovated three bedroom, four bathroom ranch style home that lives like a five bedroom on a quiet cul-de-sac neighborhood street in the Chappaqua school district. This home has undergone a comprehensive renovation in the last 8 years where every detail has been carefully crafted to blend sophistication, elegance, and functionality. The rear private yard (renderingsn are now attached) is currently undergoing an extensive leveling & expansion project. There will be a perfectly flat & fenced private backyard with a 100 ft hand laid stone wall and new patio. This will be completed in early June and approved plans are attached to listing. Embraced by a new front portico, mature trees, stone retaining wall this home enjoys a tranquil setting set nicely away from the street. Upon entry, you are greeted by a larger foyer that flows seamlessly into the living room with custom built in cabinetry & fireplace. A skylit chef’s kitchen with high end appliances, breakfast bar seating & patio access is the highlight of this home. Architectural features include a soaring ceiling in the kitchen, clean lines, an open floorplan, newly refinished oak floors, three fireplaces and large windows bathing the home in abundant natural light. A sensational four season sunroom accessed from living room offers views of the entire property. A primary suite with a luxurious en suite bathroom, two bedrooms, full hall bath with double vanity, office/den with door and powder room complete the main level. The 1200 sq foot lower level (included in the total) boasts a large recreation room with fireplace, a versatile office/den with door & stunning en suite full bath, gym room, mud room with garage access, laundry & storage. Every major system has been updated—Geothermal installed in 2023, lower level standalone AC unit replaced in 2023 and the roof in 2015 - making this home truly move-in ready. Whole house generator (2018) & solar panels (2024). Thanks to the geothermal & solar, buyers will have virtually no electric bill in the warm weather! Craftsmanship and attention to detail throughout the home. All has been meticulously cared for and renovated with luxurious materiais. This is a special residence for the discerning buyer.

$1,549,000 Pending

33 W Orchard Road Chappaqua, New York

3 Beds 4 Baths 3,814 SqFt 1.63 Acres

Classic center hall colonial with hilltop setting in desirable cul-de-sac neighborhood offering sewer/natural gas, steps from Grafflin Elem school and close to town and train., Set on gorgeous flat park-like acre surrounded by evergreens, towering trees and specimen plantings with stone walls.. Expansive Ipe deck (2012), patio, and screened porch with transom windows and high ceilings. 3 finished levels with gracious entry hall, turned side stair, family room with fireplace and bay windows (could be dining room), large open kitchen with SS Subzero/Thermador appliances, white cabinetry, granite counters, center island/skylights open to generous breakfast room with door to patio and deck, and door to screened porch with skylights and high ceilings. Formal dining room also opens to kitchen (could also be family room). 12 skylights flood the main floor of this this home with natural light. A separate main level laundry/mud room leads to the 2 car garage. The main floor is completed with a large front to back living room. The 2nd floor features oak floors throughout, primary bedroom with WIC and double closet/en-suite primary bath/skylight; 3 additional bedrooms and hall bath. The lower level offers a carpeted large playroom/rec room with room for pool/ping pong as well as media& gym area, storage/mechanical room with workbench area. Low taxes, move-in condition, great space and floorplan, top location, ready for your special touches. Probable pool site. 4 zone heat, 50 yr shingle Roof (2010), furnace & hw heater 2010, garage doors 2019. Gas line for BBQ grill.

$1,525,000 Pending

55 Old Lyme Road Chappaqua, New York

4 Beds 3 Baths 3,365 SqFt 1 Acres

Beautifully positioned at the end of a quiet cul-de-sac, this contemporary home offers style and serenity in a prime Chappaqua location. Designed with today’s lifestyle in mind, the open and airy floor plan features soaring ceilings, floor-to-ceiling windows, and sun-drenched spaces throughout. A beautifully updated modern kitchen flows seamlessly into expansive living and dining areas, ideal for both daily living and entertaining. The spacious living room opens onto a wraparound deck, creating a true indoor-outdoor living experience. The first floor also includes a wonderful private office or guest room, offering flexible space for work or hosting. Upstairs, you’ll find four generously sized bedrooms, including a primary suite with a renovated primary bath, along with an updated hall bath and convenient second-floor laundry. The finished lower level provides even more versatile living space, complete with a large recreation room and full bath and direct access to your private outdoor oasis. Step outside to a spectacular free-form pool and spa, surrounded by lush landscaping, mature trees, and tranquil lawn areas perfect for play and relaxation. This serene and sophisticated home is a rare offering in an exceptional location — a peaceful retreat just minutes from town, train, and top-rated Chappaqua schools. New Roof 2018. New Chimney 2021. Above Ground Oil Tanks.

$1,525,000 Pending

7 High Point Circle Chappaqua, New York

4 Beds 4 Baths 4,099 SqFt 1.18 Acres

Updated and well appointed 3800+ sq ft, 4 bedroom Colonial on sewer and gas in a Chappaqua, close to town, prime location. This spacious Colonial offers an ideal blend of open flow, comfort, and convenience. A gracious expansive foyer welcomes you to the light-filled living and dining rooms, both featuring bay windows. The gourmet eat-in kitchen boasts top-of-the-line finishes and appliances, seamlessly flowing into the inviting family room with a wood-burning fireplace, custom built-ins, and access to an expansive deck—an entertainer’s dream, both inside and out! The second floor showcases a luxurious primary suite w/ a spa-like bath, complete with a soaking tub and steam shower. Three additional spacious bedrooms and a renovated hall bath complete this level. The finished lower level offers incredible versatility, featuring a media room/gym, recreation room, full bath, laundry room, wine closet, mudroom, and direct outdoor access. This space can also be converted back into a garage if desired. Beautiful property offers exceptional majestic views and gorgeous sunsets plus large level play area. Abundant storage, natural gas, sewer, and sidewalks make this an exceptional home in a sought-after neighborhood close to Grafflin Elementary School and a short walk to town. Don’t miss this opportunity to enjoy the best of suburban living with close to all convenience!

$1,499,000 Pending

52 Old Lyme Road Chappaqua, New York

4 Beds 4 Baths 3,858 SqFt 1.62 Acres

Welcome to 18 Valley Lane, a four-bedroom colonial situated on a sort after quiet street in Chappaqua. The main level consists of a living room, dining room, office, powder room and a large open eat-in kitchen/family room great for entertaining with access to a screened-in porch, outdoor bluestone patio and backyard. The upstairs consists of a large primary bedroom suite with a dressing area, fitted walk-in closet and bathroom with a double sink vanity, tub and oversized glass enclosed shower. Additionally, there are 3 bedrooms, hall bathroom and laundry room. The finished lower level with access to the two-car garage can make a great play area or gym. The house is conveniently located near downtown, dining, Metro-North and Chappaqua Crossing with Whole Foods, Lifetime Fitness, Chappaqua Performing Arts Center, shopping and much more. Don’t miss this opportunity to make this your home!

$1,499,000 Pending

18 Valley Lane Chappaqua, New York

4 Beds 3 Baths 3,746 SqFt 1.32 Acres

Welcome to 20 Bristol Place, a stunning home nestled at the end of a peaceful cul-de-sac in Chappaqua, NY. This modern home boasts an open and bright layout, offering 4 bedrooms and 4 bathrooms across 4,082 square feet of luxurious living space. The oversized primary bedroom features high ceilings and a renovated bath, providing a serene retreat.

The heart of the home is the high-end chef's kitchen, complete with an oversized island, perfect for culinary enthusiasts. Enjoy cozy evenings by any of the three incredible stone fireplaces located in the living room, family room, and outside on the back deck. The property also includes a playroom, gym, updated bathrooms, oversized closets and two home offices, catering to all your lifestyle needs.

Step outside to discover a great outdoor space with two expansive decks and a private porch, ideal for entertaining or simply soaking in the sunset views. The large updated driveway with newly updated garage doors, provides ample parking.

Recent improvements enhance the home's efficiency and comfort, including a new high-efficiency boiler, water filtration and softener systems, Nest thermostats, and air purifiers. The exterior has been meticulously updated with new windows, doors, and landscaping.

Experience the perfect blend of modern amenities and tranquil living at 20 Bristol Place, where every detail has been thoughtfully designed for your comfort and enjoyment. Located in the Chappaqua School District and only 5 minutes from downtown and the train station for easy commute into NYC.

$1,495,000 Pending

20 Bristol Place Chappaqua, New York

4 Beds 4 Baths 4,082 SqFt 1.04 Acres

Discover the perfect townhouse alternative or an ideal first home just north of NYC! Nestled on Mill River Road, this inviting 4-bedroom residence offers the best of both worlds—walking distance to the charming town of Chappaqua, with its shops, restaurants, and train station, while benefiting from the highly regarded Pleasantville schools. Commuting is a breeze with the Chappaqua train station just minutes away and easy access to the Saw Mill Parkway. Enjoy the luxury of hopping on a train for dinner and a Broadway show, then returning home for a peaceful night’s sleep in the heart of Westchester. Inside, the home’s thoughtfully designed floor plan welcomes you with an inviting entrance. The newly renovated kitchen, featuring a center island, blends California bungalow charm with modern aesthetics. At the far end of the home, the sun-filled family room boasts vaulted ceilings, creating a warm and airy retreat.
Step outside to a private, low-maintenance backyard—perfect for relaxing or entertaining. Upstairs, you’ll find four spacious bedrooms. The private principal suite is tucked away on its own wing, separate from the other three generously sized bedrooms, offering a peaceful escape.
A seamless step into suburban living, this home is not to be missed. With its prime location, modern updates, and effortless lifestyle, it offers a truly sublime living experience. Enjoy full bus service to Pleasantville Schools.

$1,495,000 Active

260 Mill River Road Chappaqua, New York

4 Beds 5 Baths 3,561 SqFt 2.71 Acres

HOME IS UNDER CONSTRUCTION- READY FOR FALL 2025
2 BR Briarcliff Floorplan with primary on first floor. A finished basement with full bath give plenty of room for everyone to enjoy.

This outstanding home is located in a great location facing greenspace on one side and forest views from the rooftop deck. It is located in the heart of the neighborhood where you can walk to shopping, cafes, gym and more. It is ideally sized at 2,945 sq. ft. and includes 2 BR + office, loft giving you plenty of space for everyone to enjoy. The open concept 2- story great room and kitchen allow for large family gatherings. The open island with ample seating beckons your inner chief to come alive. A roaring fireplace will warm the entire home. A private rooftop terrace, 2- car garage and the highest quality interior appointments you've come to expect from Toll Brothers round out this spectacular residence! Once completed this 91- Townhome community will surround it's owners with a delightful and eminently walkable village full of the niceties that make Westchester living so extraordinary; such as charming cafes, fitness center, golf, shuttle to train into Manhattan, walking trails, pool, clubhouse, and much more! All design selections have been selected and are included in price. Our design team went above and beyond and this home will be finished like a model! Additional Information: ParkingFeatures:2 Car Attached,

$1,480,995 Pending

14 Carriage Lane 87 Chappaqua, New York

2 Beds 4 Baths 2,945 SqFt

Welcome to 24 Glen Terrace, Chappaqua, a gracious and well-maintained Colonial imbued with country charm serenely set at the end of a quiet cul-de-sac. Welcoming tiled entry foyer introduces expansive front-to-back living room with double French doors, large front-facing bay window and slider to rear deck. Adjoining formal dining room with fireplace easily accommodates feasts or fests. A skylit, cathedral ceiling tops the eat-in, gourmet chef's kitchen outfitted with high-end stainless-steel appliances, custom cabinetry, granite countertops, plus a breakfast area with wood-burning fireplace & French door to deck for easy BBQ and alfresco dining. Versatile main-level home office/den/study/studio/guest space. Hardwood flooring runs throughout. Convenient main-level mudroom accesses front yard, powder room, kitchen and 2-car attached garage for short distance from trunk to pantry. Upstairs is home to four comfortable bedrooms including the front-to-back primary suite with private ensuite bath, front- and rear-corner bedrooms with two exposures, and a cozy bedroom with two windows, all with hardwood flooring, and a windowed hall bath with natural stone-topped vanity and shower over bathtub. Mature and established landscaping adds seasonal color and privacy to the serene setting bordering 17 acres of town-preserved land at the end of a quiet cul-de-sac just a short drive to schools, shops, town and train.

$1,475,000 Active

24 Glen Terrace Chappaqua, New York

4 Beds 3 Baths 2,539 SqFt 1.167 Acres

Discover the perfect blend of elegance and comfort in this beautifully updated four-bedroom colonial, nestled in the coveted Glen Terrace cul-de-sac. This exceptional home is filled with natural light, enhanced by designer-selected colors, stylish light fixtures, and recessed lighting.
The heart of the home is the spacious eat-in kitchen, featuring premium finishes such as Emerald Green granite countertops, a Rohl sink faucet, a Sub-Zero refrigerator, and a Bosch dishwasher. Flowing seamlessly into the inviting family area with a cozy fireplace and sliding glass doors to an expansive deck. A layout that is perfectly designed for effortless indoor-outdoor living. Rich dark hardwood floors extend through the living and dining rooms, which are thoughtfully defined by elegant picture-frame molding and custom built-in cabinetry. Upstairs, the recently expanded primary suite boasts a vaulted ceiling, walk-in closets and stunning seasonal views of the picturesque property. Adjacent to the suite, a generous office space with an additional full bath that offers versatility for work or relaxation. Three additional charming bedrooms with their convenient large hall bath. The lower level provides flexible space ideal for a rec room, home office, or gym. Throughout the home, California Closets enhance storage, including in the basement. Major recent upgrades, including new windows (2019), a new roof (2019), a new furnace (2023), and a full-house generator (2020) add both value and peace of mind. Professionally landscaped property featuring a recently fenced-in large level lawn, mature specimen trees, and lush flower gardens, creating a private oasis. Fall in love with this exceptional home!

$1,425,000 Pending

10 Glen Terrace Chappaqua, New York

4 Beds 4 Baths 3,219 SqFt 1.01 Acres

Fabulous 3 Bedroom Home which lives like 4 Bedroom on rare and lovely cul-de-sac within a 5-minute walk to the nationally ranked Horace Greeley High School, part of the award-winning Chappaqua School District, and to Chappaqua Crossing with its charming shops and restaurants, including Whole Foods, Life Time Gym, Starbucks, and the Chappaqua Performing Arts Center. It is also in close proximity to the Saw Mill River Parkway and Downtown Chappaqua. This location is one of the best in Chappaqua and is highly coveted. This lovingly-maintained home is flooded with sunlight and has all new windows and doors, which provide easy access to and enjoyment of its lush landscaping and beautiful perennial gardens. Substantial Entry Foyer with Closet leads to large open plan Living Room with stone wood burning fireplace, custom built-ins, and separate Dining Area. Sliding glass doors in Living Room lead to expansive Deck with steps to Lower Patio which is ideal for Outdoor Firepit. There is a tremendous amount of room for entertaining! The Kitchen is beautifully renovated with stainless steel appliances, and a Breakfast Nook. Additional rooms on the first floor include a very large and sunny Primary Bedroom with an oversized picture window, two ample closets, and a Primary Bathroom, one additional Bedroom, a large and well-appointed Office/Bedroom, and a Hall Bathroom with gleaming hardwood floors throughout the first floor. Lower level is fully finished with a Yoga/Exercise Room, Office/Bedroom with another stone wood burning fireplace, luxurious Bathroom with Steam Room, and a separate Entrance which opens on to the Lower Patio, ideal for au pair, mother-in-law suite, or overnight guests from the city! The Attic is accessed by a full staircase, provides an enormous amount of storage, and is ready for substantial expansion possibilities. Do not miss this wonderful Home with its spectacular location close to everything Chappaqua has to offer! New Septic Fields, New Water Heater, and Newly Paved Driveway.

$1,425,000 Active

4 Southview Road Chappaqua, New York

3 Beds 3 Baths 2,111 SqFt 0.7 Acres

2 BR Primary on first floor home. Large Eat in kitchen with island, open to great room and dining room. Second floor office and wet bar makes entertaining easy on rooftop terrace with built-in kitchen BBQ. Lower level is finished with media room and full bath.

$1,399,995 Pending

13 Wallace Way 19 Chappaqua, New York

2 Beds 4 Baths 2,945 SqFt

HOME IS UNDER CONSTRUCTION. MOVE in SUMMER 2025.
2 BR, 3 Full, 1 half primary on main floor, finished basement with full bath and media room. Additional Information: ParkingFeatures:2 Car Attached,

$1,399,995 Pending

8 Dewitt Drive 66 Chappaqua, New York

2 Beds 4 Baths 2,945 SqFt

Meticulously maintained move-in ready home on a park-like acre with an incredible flat, usable and private backyard with extensive mature trees and landscaping. This 3 bedroom/ 3 full bathroom house with hardwood flooring and recessed lighting throughout, has a perfect option for an additional guest bedroom/ office on the first floor and countless special features such as an in-ground sprinkler system, smart thermostats, door locks, alarm and lighting; plus a sizable space above the garage for possible expansion. There is a light and bright living room with cathedral ceiling and oversized bay window, adjacent to the dining room also with cathedral ceiling and custom bookshelves and cabinetry and access to an amazing screened-in porch that was recently updated and is set up to be usable for 3 seasons and has access to the back deck. The updated kitchen has high end stainless steel appliances, granite countertops, 2 sinks and a window surrounded eat-in area with vaulted ceiling, skylight and ceiling fan. There is a laundry room several steps down from the kitchen and an inviting family room with floor to ceiling windows, a stone encased wood burning fireplace, built-in sound bar and speakers and a glass door to the backyard and patio and access to the first floor full bathroom and office/ guest room. The upper level offers a primary bedroom with a walk-in and double closet and an updated primary bathroom, 2 additional bedrooms, a hall bathroom and 2 linen closets. In the finished lower level there is a recreation room, a mudroom with access to the garage and 3 spacious storage rooms. This impeccable offering in a coveted Chappaqua neighborhood is located close to everything including town, Chappaqua Crossing and more and is not to be missed!

$1,375,000 Pending

42 Cross Ridge Road Chappaqua, New York

3 Beds 3 Baths 3,102 SqFt 1.03 Acres

Welcome to 23 Round Hill Road, a picture-perfect, timeless, Center Hall Colonial on a premier street just minutes from Chappaqua schools, train station, & a variety of restaurants, shops & grocery stores (including Whole Foods & Starbucks), a prime location for convenience & lifestyle. Set on a beautifully landscaped property, this home exudes classic appeal. As you step through double front doors into the expansive entry hall, you're greeted with a feeling of openness & flow, leading you effortlessly into the bright, spacious living room complete with a traditional fireplace & a large bay window overlooking the front yard. French doors open to a lovely screened-in patio that’s bathed in sunlight, an ideal spot to sip your morning coffee or unwind at the end of the day. A formal dining room connects seamlessly to the eat-in kitchen, which offers direct access to the attached two-car garage for added convenience. Just off the kitchen, you'll find a hallway including the laundry area & back door that leads to the backyard, patio, & pool, making outdoor living & summer fun a breeze. A charming den with built-ins, perfect as a home office or cozy library, also opens onto the screened-in patio. A powder room completes the main level. Upstairs, a wide hallway leads to five spacious bedrooms, including a primary suite with its own en-suite bath. Ample closet space throughout, plus pull-down stairs to a full, unfinished attic offer plenty of storage. Downstairs, the walk-out lower level includes all mechanicals & is ready for you to transform into whatever suits your lifestyle-whether it’s a gym, media space, or bonus area. Outdoors, you'll fall in love with the large trees in the front yard & fully fenced backyard, complete with a patio, whole-house generator, & a swimming pool. This is the perfect setting for gatherings, play, or peaceful afternoons at home. Both the home & pool are being sold as-is, offering a rare opportunity to make this home truly your own in a prime Chappaqua location. Make this home yours & start celebrating life's moments in style. The assessment has recently been successfully grieved & the taxes on the MLS report are the correct new taxes.

$1,375,000 Pending

23 Round Hill Road Chappaqua, New York

5 Beds 4 Baths 3,230 SqFt 1.27 Acres

Discover the enduring charm of this distinguished 1937 Country Colonial, offering over 4,000 square feet of dramatic, sun-filled living space. Majestically sited on over one beautifully landscaped acre, this home features level play areas and exceptional outdoor entertainment spaces, seamlessly blending classic elegance with modern updates. The impressive Great Room captivates with its vaulted ceiling, striking stone fireplace, and French doors that open to a private deck, creating a perfect retreat. A formal Dining Room sets the stage for elegant gatherings, while the renovated Kitchen flows effortlessly into the inviting Family Room, complete with a cozy fireplace. Designed for today’s lifestyle, a spacious Office provides a comfortable work-from-home space. Upstairs, the Primary Suite features a wood-burning stove, dressing area, walk-in closet, and a full bath. Two additional Bedrooms and a Hall Bath complete this level. The Lower Level Recreation Room offers versatile space for play, fitness, or media. Outdoor living is exceptional, featuring outdoor lighting, a tiered bluestone terrace with a built-in Viking barbecue, and a fenced sport court with a basketball hoop, perfect for year-round enjoyment. Surrounded by mature trees, specimen plantings, and charming stone walls, this home offers a private and picturesque setting while being just moments from Chappaqua’s vibrant town center, train station, major highways, and top-rated schools. Recent updates include: new above-ground oil tank, newer roof, freshly painted interior & exterior. A rare opportunity to own a piece of Chappaqua history—this exceptional home is not to be missed!

$1,350,000 Pending

25 Campfire Road Chappaqua, New York

3 Beds 4 Baths 4,086 SqFt 1.26 Acres

Spacious 4 bedroom/ 4 bathroom home that lives like a 5+ bedroom in a coveted Chappaqua neighborhood. Light and bright freshly painted updated home with hardwood floors throughout. The first floor has an entry foyer, powder room, eat-in-kitchen with granite countertops and new stainless steel appliances, living room/ dining room with fireplace and sliding doors to a wrap around deck also accessible from the kitchen. Several steps up lead a hall bathroom, the primary bedroom and bathroom, 3 additional bedrooms plus an office perfect for a fifth bedroom. The light and bright walkout lower level offers a spacious family room with a vaulted ceiling, a recreation room and another finished space perfect for a nanny room or playroom, plus a full bathroom and lots of storage spaces. There is a fenced in flat and usable backyard as well. This amazing home offers lots of living space and has recently installed solar panels and a GREE energy efficient heating and cooling system with 10 zones, to make it very energy efficient. It is a great home in a highly desirable, well situated Chappaqua neighborhood and is not to be missed!

$1,350,000 Pending

23 Cross Ridge Road Chappaqua, New York

4 Beds 4 Baths 3,525 SqFt 1.04 Acres

HOME IS UNDER CONSTRUCTION- READY FOR Summer 2025 closing
2 BR Briarcliff Floorplan with primary on first floor. You can still add structural and design features to this home.

This outstanding home is located in a great location facing greenspace on one side and forest views from the rooftop deck. It is located in the heart of the neighborhood where you can walk to shopping, cafes, gym and more. 2 BR + office, loft giving you plenty of space for everyone to enjoy. The open concept 2- story great room and kitchen allow for large family gatherings. The open island with ample seating beckons your inner chief to come alive. A roaring fireplace will warm the entire home. A private rooftop terrace, 2- car garage and the highest quality interior appointments you've come to expect from Toll Brothers round out this spectacular residence! Once completed this 91- Townhome community will surround it's owners with a delightful and eminently walkable village full of the niceties that make Westchester living so extraordinary; such as charming cafes, fitness center, golf, shuttle to train into Manhattan, walking trails, pool, clubhouse, and much more! All design selections have been selected and are included in price. Our design team went above and beyond and this home will be finished like a model! Additional Information: ParkingFeatures:2 Car Attached,

$1,338,995 Pending

14 Carriage Lane 87 Chappaqua, New York

2 Beds 3 Baths 2,503 SqFt

Welcome to a sleek contemporary home that seamlessly blends indoor comfort with an exceptional outdoor retreat. From the moment you enter, you'll appreciate the design's focus on chic, easy living, bathed in natural light and showcasing exposed beams, custom built-ins, and premium appointments. This home boasts an open concept and has been fully updated, living generously like a 4 or 5-bedroom residence. The versatile lower level is a true bonus, offering a family room with a second fireplace, a wet bar perfect for entertaining, a guest room, a bathroom, and a flexible two-room office suite. Both levels feature glass doors that lead to three levels of decking, providing abundant space for outdoor enjoyment and tranquil views. Set on a hillside, this property offers a feeling of a private, elevated treehouse, ideal for entertaining or simply unwinding. Enjoy the convenience of being close to Chappaqua's town amenities and train station.

$1,275,000 Active

57 Hamilton Drive Chappaqua, New York

3 Beds 3 Baths 3,728 SqFt 0.9 Acres

Welcome to 26 Mayberry Road, a charming and spacious 5-bedroom expanded ranch-style home on a quiet cul-de-sac street in the Chappaqua school district. Set on a private, landscaped acre, this home offers scenic views from the elevated deck and large stone patio just off the walkout lower level. The main floor features a versatile and inviting layout with formal living and dining rooms, a kitchen open to the breakfast area, and a family room featuring a wood-burning fireplace with heat insert, skylight, and stairs up to a bonus/playroom over the garage. The family room has direct access to a fully enclosed 3-season sunroom and upper deck with stairs down to the stone patio below. The first floor also includes the primary bedroom with an en-suite bathroom, a home office, and an additional full bathroom. Upstairs, there are four generously sized bedrooms and a full bathroom. The walkout lower level has a sliding glass door to the patio and includes an additional 900 square feet of finished storage, a dedicated laundry room, and plenty of utility/storage areas.

$1,265,000 Active

26 Mayberry Road Chappaqua, New York

5 Beds 3 Baths 3,200 SqFt 1.1 Acres

Inside & outside blend seamlessly together throughout this sleek, modern 3-bed/2-bath contemporary, wrapped by a massive deck front, side & rear, and privately set back from the road on two peaceful, sylvan acres on a cul-de-sac in the sought-after Whippoorwill neighborhood. Great layout for entertaining. Arts & crafts-inspired living room illuminated by large front-facing windows & topped with a dramatic wood-finished cathedral ceiling, end-capped by two large triangular clerestory windows, comforted by a lighted ceiling fan, and connected to the deck by a wide sliding glass door. The adjoining dining room is softly lit by sliding window sets front & rear, and capped with a beamed, wood-finished ceiling. Hardwood flooring runs throughout the living & dining rooms. Chef's will relish the designer, eat-in kitchen smartly outfitted with stainless steel appliances including a wide, 36-inch Viking Professional 6-burner range with pot-filler faucet & matching hood, GE refrigerator/freezer, GE microwave oven & KitchenAid dishwasher. The built-in cabinetry is artfully designed. Granite countertops blend the room together. Casual dining is a pleasure in the breakfast area. A built-in corner buffet & glass-doored cabinet add both style & utility. A large sliding glass door gives quick access to the deck for easy BBQ or alfresco dining. Tile backsplash & flooring, plus a wood-finished beamed ceiling complete the decor. The private quarters are composed of three bedrooms and two bathrooms. All bedrooms have a wood-finished, beamed ceiling & hardwood flooring. The primary suite is endowed with a walk-in closet, second closet & private ensuite bath with shower. The shared hall bath enjoys a shower over a jetted bathtub. Further relax and spread out in the downstairs family room which also features a sliding glass door to outside. Also stationed downstairs are laundry, mechanicals & utilities, and storage. Nature's bounty envelopes your retreat outside to entertain, play, or relax, either on the massive wrap-around deck, on the lawns around the residence, or in the wooded portion of the yard. A private oasis on two acres, seemingly a million miles away from anywhere, yet fortuitously set in the prestigious Whippoorwill section of Chappaqua, just a short ride to schools, shops, town & train.

$1,200,000 Pending

64 Stornowaye Street Chappaqua, New York

3 Beds 2 Baths 2,144 SqFt 2.028 Acres

This beautiful Chappaqua house sits on 3.25 acres surrounded by formal gardens and woods. Designed by the renowned Westchester architect James Renwick Thomson in the 30's, this home seamlessly incorporates both elements of formal sophistication along with more casual charm. It is a one-of-a-kind gem, containing Palladian windows, vaulted ceiling, custom wood work, bay windows, Dutch doors, roughhewn beams and a second-floor terrace for dining al fresco. The grounds include formal gardens with multiple sitting areas, two koi ponds, and pebbled pathways. The red clay tennis court, stream, and long driveway add to the property's unique qualities. Join one of the many swim and tennis clubs minutes away. All this in the award-winning Chappaqua School District. Convenient to NYC by either car or train.

$1,200,000 Active

124 Seven Bridges Road Chappaqua, New York

3 Beds 2 Baths 1,918 SqFt 3.25 Acres

Storybook 1930’s-era Tudor-style shingle cottage delightfully renovated & updated with all the comforts for the 21st century. Believed to be originally derived from Standard Homes Co. classic Densmore model. A welcoming entry vestibule with French door introduces a wide, front-facing living room, warmed by a stout wood-burning fireplace. Gather together in the dining room to enjoy holiday feasts artfully prepared in the modern, gourmet chef's kitchen outfitted with upscale appliances, functionally beautiful cabinetry, all sweetly accented by a backsplash of small glass subway tile. Relax, play or entertain in the large & inviting family room which adjoins the kitchen and enjoys light exposures on three sides including floor-to-ceiling windows & French doors which bring the outside in. An expansive bluestone terrace lays just beyond. The sun parlor is an ideal spot for more solitary pursuits, like reading, painting, practicing a musical instrument, or working from home. A small powder room completes the main level. A proud, L-shaped staircase ascends to the upper-level, home to a front-corner bedroom; a side-facing bedroom; an updated hall bath with glass-walled shower with bench, radiant heat & heated towel rack; an enchanting primary suite, endowed with a high ceiling, dramatic rear-facing windows, and luxurious ensuite bath with radiant heat & heated towel rack; and a front-facing den/study, which could also serve as a home office, and has a staircase ascending to the full attic. Downstairs houses an unfinished basement with laundry, natural gas utilities, storage, and access to the 1-car attached garage. With central air conditioning, municipal water and sewer. The outside grounds are very attractive. A bluestone terrace spreads out from the family room. Five wide steps lead from the terrace up to a lush lawn blanketing the back yard. Lovely, well-tended landscaping surrounds the property. A true village charmer just a short stroll to shops, schools, town & train.

$1,200,000 Pending

45 Crossways Chappaqua, New York

3 Beds 3 Baths 2,246 SqFt 0.25 Acres

Welcome to 29 Begg Drive, a meticulously-maintained gem in Chappaqua! This serene property features an open floor plan with hardwood floors, charming traditional architectural features, and numerous upgrades. The sunlit first floor features a kitchen with a large picture window, a living room area, and a dining area. An attached screened-in porch, which overlooks the yard and connects to a large refurbished exterior deck, is a love place to relax and enjoy the bucolic views. The 2nd level features a full bath, 2 bedrooms, and a home office. Continue to the 3rd level, which boasts a newly updated primary suite with skylights, walk-in closets, and fully renovated bathroom. The basement level, with a laundry and utility room, offers additional space and many opportunities. Outside, lush landscaping with mature shade trees create a private setting to enjoy for years to come, with a stone patio for additional outdoor entertainment. This picturesque home is close proximity to Metro North and downtown Chappaqua, which features delightful shops and restaurants, a fantastic library, a thriving farmer's market, and award-winning schools.

$1,200,000 Active

29 Begg Drive Chappaqua, New York

3 Beds 3 Baths 2,000 SqFt 0.43 Acres

Live minutes from the heart of Chappaqua! Commuters dream to live in this charming tudor-style home near all everyday amenities. Nestled on 1.11 acres, with 3-bedrooms and 2 bathrooms, this fully renovated residence offers timeless character and thoughtful updates throughout. The main level features an inviting entry foyer, a chef’s eat-in kitchen equipped with a gas oven/range, microwave, and dishwasher, great for cooking and hosting. Step into the spacious living room with a cozy stone fireplace, den/office space, full bathroom and laundry hook up completing the first floor. On the second level, the primary bedroom offers a walk-in closet, along with two additional bedrooms and full bathroom. Distinctive interior details include beamed ceilings, crown molding, original woodwork, and recessed lighting. Enjoy hardwood floors throughout, central A/C, laundry hookups, and ample storage with a full attic and partial unfinished basement. The exterior is equally impressive with stone-accented driveway, peaceful surroundings the large front and back yards. Quiet and desirable street with no through traffic. Close to all, don't miss out on this opportunity!

$1,199,000 Active

34 Glenside Place Chappaqua, New York

3 Beds 2 Baths 1,880 SqFt 1.11 Acres

Picture perfect Cape on level landscaped property with lush lawns radiates curb appeal. Beautifully updated and impeccably maintained with a blend of classic charm and modern luxury. Light-filled rooms with gleaming hardwood floors enhance the well proportioned living spaces. The renovated eat-in kitchen features white cabinetry, stainless steel appliances, quartz countertops and tasteful finishes. The living room with large fireplace and picture window welcome you into the home and the expansive dining room with convenient access to a peaceful covered porch offer easy entertaining and comfortable living. A cozy family room with custom built-ins is ideal for relaxation or work from home flexibility. A large first floor bedroom and renovated full bathroom complete the main level. Upstairs the generously sized primary bedroom features a walk in closet, a recently renovated full bathroom and a large bedroom with two closets and built in cabinets. The finished lower lever offers a flexible floor plan, perfect for a recreation room, family room or playroom. The gym could easily be used as a fabulous home office or guest room. The lower level includes a full bathroom, laundry, ample storage, updated mechanicals, access to two car garage and a convenient door to the backyard.
Enjoy outdoor living on the inviting covered porch, or host gatherings in the expansive backyard framed by mature trees and lush landscaping. With generously sized rooms, a thoughtful layout, and high-quality upgrades, this home is truly move-in ready. Tucked away on a quiet cul-de-sac and just a short stroll to town, train, shops, and Bell Middle School this turn-key home is not to be missed!

$1,199,000 Pending

12 Pond Hill Road Chappaqua, New York

3 Beds 3 Baths 2,652 SqFt 0.78 Acres

Picture-perfect Colonial in Chappaqua's highly sought after Lawrence Farms South neighborhood. Beautifully updated and impeccably maintained 3-bedroom, 3.5-bath home sits on nearly an acre of level, landscaped property with lush lawns and unparalleled curb appeal. Radiating a perfect blend of classic charm and modern luxury, this home welcomes you with light-filled, well-proportioned living spaces and gleaming hardwood floor.
An elegant staircase greets you in the foyer showcasing the graceful lines and rich woodwork characteristic of 1930s architecture. The expansive living room features a large fireplace and picture windows, creating a warm and inviting atmosphere. Timeless French doors lead to a beautiful sunroom perfect for enjoying the four seasons. The formal dining room with large slider to the large patio makes entertaining effortless, while the cozy family room with custom built-ins offers the ideal space to relax or work from home. The renovated eat-in kitchen boasts white cabinetry, quartz countertops, stainless steel appliances, an island with ample seating and tasteful finishes—designed for both beauty and functionality. Upstairs the luxurious primary suite offers a tastefully renovated en-suite bathroom and two large closets. There are two additional bedrooms on the second floor, one that is en-suite and one that id conveniently located across the hall from a full bathroom. A rear staircase brings you back to the kitchen and easy access to the attached two car garage.
Enjoy outdoor living on the inviting patio and host gatherings on the sweeping lawn framed by mature trees and lush landscaping. Just a short walk to town, train, shops and schools, this move-in-ready gem is tucked away on a private road in one of Chappaqua’s most desirable neighborhoods.
A rare offering-not to be missed!

$1,199,000 Active

33 High Way Chappaqua, New York

3 Beds 4 Baths 1,917 SqFt 0.95 Acres

Welcome to this enchanting, character and light-filled Colonial, nestled on beautiful grounds in the sought-after Chappaqua school district. This gracious home blends timeless character with modern updates, featuring a WOW chef’s kitchen with stainless appliances, a travertine countertops, that has been proudly showcased in Old House Journal magazine. Thoughtfully designed for both everyday living and entertaining, the home boasts an elegant entry hall with gleaming cherry floors that flow seamlessly into the kitchen. The spacious living room is anchored by a cozy wood-burning fireplace and offers stunning views of the lush backyard through oversized windows and a large dining room is sophisticated and inviting. Adjacent to the living room, a wood-paneled library/office includes custom built-ins and more of those sun-drenched windows, creating the perfect work-from-home sanctuary. Upstairs, the primary bedroom includes a renovated en-suite bath, while two additional bedrooms share a beautifully updated hall bath. The walkout lower level is a true bonus space, offering an office, gym, play area, and full bath. The home also enjoys a heated mudroom for year-round convenience. Outdoor living is just as exceptional. Enjoy tranquil moments by the pond and babbling brook—complete with a charming bridge. Specimen plantings and a whimsical playhouse with electricity (ideal for a yoga studio, art space, or children's play space) add to the home's storybook feel. The expansive flagstone patio invites alfresco dining and entertaining in a peaceful, private setting. Not to be missed!

$1,149,000 Active

326 Millwood Road Chappaqua, New York

3 Beds 4 Baths 2,313 SqFt 1.37 Acres

Move right into this walk-to-town beautifully updated 4-bedroom, 2.5-bath Colonial that offers the perfect balance of classic charm and modern convenience. Just steps from the heart of Chappaqua, this home features an open-concept layout and flexible spaces ideal for everyday living and effortless entertaining.
Step through the storybook Dutch door to a light-filled, double-height entry with a skylight and elegant wraparound staircase. The open floorplan offers flexible spaces that can change and evolve with your lifestyle. The sun-drenched updated chef’s kitchen is the centerpiece of the home with generous custom recessed panel cabinetry, large center island seating and stainless steel appliances. It is open to the living and dining areas with custom built ins. Lovely architectural beamed ceilings and a charming fireplace add warmth and character to the living room.
On the first floor, a versatile bedroom (currently used as a den) boasts elegant French doors and an adjacent half bath. With room to add a shower, this space can easily be transformed into a guest suite or convenient first-floor primary.
Upstairs, the generously sized primary suite offers soaring vaulted ceilings, abundant natural light and a newly renovated ensuite bath with double vanity, whirlpool tub and skylight. The second bedroom also features vaulted ceilings and a cozy loft area that is perfect for a reading nook, study space, or creative hideaway. Another bedroom with expansive closets and a newly updated hall bath complete the upper level.
Tucked behind the home, a charming patio with high-end, easy-care turf and lush, vibrant plantings offers a serene spot to enjoy your morning coffee or unwind at the end of the day.
This home has been thoughtfully transformed with numerous recent upgrades including stunning newly refinished floors, fresh interior and exterior paint, lighting, mechanicals and more.
Don’t miss this special Chappaqua gem where charm, convenience, and turnkey living come together in perfect harmony.

$1,099,000 Pending

5 Crossways Chappaqua, New York

4 Beds 3 Baths 2,212 SqFt 0.21 Acres

Welcome to this lovely home within the very desirable Hillholme community in Chappaqua. Perfectly maintained and set beautifully on a flat large acre for all to enjoy. The bedrooms are all very spacious, there is a dedicated home office/study that ensures productivity, while the basement adds a great space for a play area. The backyard is a dream - lush green grass, deck and patio for barbecues and entertaining. Convenient access to shopping, dining, train and of course our top - rated schools. New roof, Generator, AC system ,Floor plans are up in photos
SHOWINGS begin at noon on 3/7

$1,099,000 Pending

132 Devoe Road Chappaqua, New York

3 Beds 3 Baths 2,533 SqFt 1.08 Acres

Spacious Turn-of-the-Century Converted Cider Mill – A True One-of-a-Kind Home! Nestled on just over 1 acre of lush property, this sprawling and unique home was once a cider mill and has been beautifully converted into a spacious residence. Boasting 3 working fireplaces and retaining many of its original architectural details, this home exudes character and charm. With hardwood floors, high wood beam ceilings, and enormous rooms, it’s a perfect blend of historic elegance and modern potential—offering the opportunity to update the kitchen and bathrooms to your own taste. The sunken living room, with its soaring ceiling and cozy fireplace, sets the tone for a warm, inviting space. With 5 generously sized bedrooms, a huge terrace room with a cathedral ceiling, formal dining room, and two playrooms, there is no shortage of space for family, guests, and entertaining. Outside, enjoy the tranquil surroundings with a patio and an oversized 2-car garage. The property is located on a corner lot on a dead-end street, offering added privacy and peacefulness. It borders the Pruyn Sanctuary, a 92-acre nature preserve with over two miles of scenic hiking trails, providing a picturesque setting and an abundance of outdoor activities right at your doorstep. Conveniently located near schools, Gedney Park, shops, a bike trail, and major parkways, this home offers both seclusion and accessibility. Don't miss out on the chance to own a piece of history in one of the most serene and sought-after locations. There are no audio recording devices inside this property.

$1,075,222 Pending

2 Woodmill Road Chappaqua, New York

5 Beds 4 Baths 5,227 SqFt 1.1 Acres

$1,049,000 Active

100 Castle Road Chappaqua, New York

3 Beds 4 Baths 2,590 SqFt 0.22 Acres

Welcome to 8 Elizabeth Street – A Charming, Turnkey Colonial nestled on a quiet cul-de-sac street. A beautifully updated three-bedroom, two-and-a-half-bathroom Colonial that seamlessly blends style, comfort, and convenience. Step inside to discover a thoughtfully designed layout, where large, updated windows flood the home with natural light. The spacious living room is an inviting gathering space, featuring a stunning brick fireplace, a large bay window, and gleaming hardwood floors. The formal dining room flows effortlessly into the updated kitchen, perfect for both everyday living and entertaining. Enjoy your morning coffee in the charming breakfast nook or step through sliding glass doors onto the expansive deck—ideal for dining al fresco or relaxing in the fresh air.
The primary suite is a private retreat, offering an en-suite bath, three walls of windows, and two generous closets. Two additional bedrooms, a full bathroom with a bathtub, and a convenient second-floor laundry room complete the upper level. The lower level provides endless possibilities, with flexible space for a home office, playroom, or additional living area, plus sliding doors that open to a private patio. Outside, the expansive lawn and multiple outdoor living areas create a peaceful escape—perfect for entertaining or simply unwinding in nature. Located just minutes from downtown Chappaqua’s charming shops, restaurants, train station, schools, and parks, this home offers the perfect balance of privacy and accessibility.
Don't miss this exceptional opportunity to make this house your home!

$999,000 Pending

8 Elizabeth Street Chappaqua, New York

3 Beds 3 Baths 1,824 SqFt 0.65 Acres

Welcome to 74 Seven Bridges Road in Chappaqua—a home that perfectly blends comfort and style.

This inviting home features an open floor plan designed for effortless living and entertaining. Enter into a large foyer with a smart mud room tucked away to the side. Here you also have direct and easy access to the garage. Once inside you will appreciate the warmth and sophistication this home offers. A wood-burning fireplace anchors the sun drenched first-floor living area, creating a cozy ambiance year-round. The eat-in kitchen is the heart of the home, offering a bright and welcoming space to cook and to gather. Here there is also a door to the yard as well.

With three bedrooms plus a dedicated office, this home provides the flexibility to meet your needs. All three bedrooms are spacious and bright. The lower level, although unfinished, has the laundry, tremendous storage, and a door out to the expansive, private, and fenced backyard. This level offers endless possibilities.

Nestled in a peaceful setting yet conveniently close to Chappaqua’s vibrant town center and transportation, this home is the perfect retreat. Welcome home!

$989,000 Pending

74 Seven Bridges Road Chappaqua, New York

3 Beds 2 Baths 2,018 SqFt 1.07 Acres

Nestled in the heart of Chappaqua, this enchanting stone and wood colonial is move in ready with updates throughout! This two bedroom two and a half bath residence lives like a three bedroom! Just a short walk to shopping, restaurants, parks, school and the train. Beyond the inviting front porch you will find both comfort and charm. The main floor has beautiful beamed ceilings throughout and a vaulted cathedral ceiling in the living room. The updated chef's kitchen boasts top of the line appliances. Step out of the french doors from the cozy interior to a spacious deck, offering tranquil treetop views—a perfect retreat for morning coffee or evening gatherings.

Upstairs you will find the primary suite and two additional rooms, as well as a newly renovated hall bath along with the laundry room. The primary bedroom is spacious and light filled with two large closets a newly renovated spa like en suite bathroom.

Discover the essence of Chappaqua living, a perfect transition from the city to suburban living!

$949,000 Pending

12 Spring Lane Chappaqua, New York

2 Beds 3 Baths 2,440 SqFt 0.16 Acres

Nestled on nearly 2 acres of serene, wooded land, this beautifully maintained 4-bedroom, 2.5-bath home offers space, comfort, and privacy. The bright and airy eat-in kitchen features abundant cabinet space, a convenient in-kitchen laundry, and a large picture window overlooking the scenic backyard. A sun-filled living room with an oversized picture window enhances the home's warm and inviting atmosphere. The generously sized bedrooms provide ample space for relaxation, while the renovated lower level boasts all-tile flooring, a cozy wood-burning fireplace in the family room, an additional bedroom, a powder room, and plenty of storage. Enjoy outdoor living on the spacious deck, perfect for entertaining or unwinding while taking in the tranquil surroundings. The upper level of the private yard offers even more space, perfect for a fire pit or additional outdoor activities. Additional highlights include a full-house generator for year-round peace of mind, freshly painted interior, and hardwood floors under the carpeting. A perfect blend of space, functionality, and charm, this home is ready to welcome its next owners!

$899,000 Active

341 Millwood Road Chappaqua, New York

4 Beds 3 Baths 2,541 SqFt 1.93 Acres

Step into a beautifully refreshed Chappaqua residence. This inviting home boasts stunning wooded views, creating a serene and tranquil atmosphere. The thoughtfully designed layout flows seamlessly, connecting a spacious formal living room, an elegant dining area, and a bright, eat-in kitchen. From the kitchen, step out onto a large deck, perfect for alfresco dining and entertaining amidst the natural beauty of the surroundings. The home features a comfortable primary bedroom with a full en-suite bathroom, along with three additional well-proportioned bedrooms and a shared hall bath. The lower level adds and additonal 1066 sqft bringing the total square footage to 2954 and offers even more flexible living space, including an expansive family room ideal for relaxation and recreation. A versatile office or workshop area provides space for creative pursuits or professional needs. Added conveniences include a dedicated laundry room and a convenient powder room. Situated on a level lot, the property offers a generous backyard, providing ample space for outdoor enjoyment. This Chappaqua home offers a harmonious blend of modern updates, natural beauty, and functional living spaces, all within a community known for its peaceful suburban setting and convenient access to New York City

$899,000 Pending

16 Garey Drive Chappaqua, New York

4 Beds 3 Baths 1,888 SqFt 1.03 Acres

Welcome to a home full of warmth, charm, and everyday comfort — perfectly situated right across from beautiful Gedney Park and just around the corner from the elementary school.

This inviting 4-bedroom, 2.5-bathroom home has everything you need for easy, relaxed living. Step inside to a bright and welcoming living room, a private office ideal for working from home, and a comfortable family room made for movie nights and cozy weekends. The open kitchen flows into the dining area, creating the heart of the home — a place where everyone can gather, cook, and connect.

Upstairs, you'll find four bedrooms, including a primary with its own full bath and walk-in closet, another full bath just down the hall.

Outside, the beautiful yard is a true highlight — with plenty of room to play, garden, or simply unwind under the lovely pavilion, perfect for relaxing afternoons or casual get-togethers.

With parks, schools, and nature right at your doorstep, this home offers the perfect blend of comfort, convenience, and charm. Come make it your own!

$879,000 Pending

180 Millwood Road Chappaqua, New York

4 Beds 3 Baths 2,334 SqFt 1.04 Acres

Contemporary bi-level 4 beds 2 Bath home. Enjoy comfort and sophistication with red oak hardwood flooring, recent upgrades like a new roof, boiler, and sanitary system. Large living room with ample space for holiday gatherings. Entertain effortlessly with three freshly stained multi-level decks, perfect for parties and functions. Large yard to enjoy outdoor activities, with three sheds, offers plenty of outdoor storage . Located in Chappaqua P.O. within the prestigious Pleasantville School system, enjoy convenience with a Rare FREE SCHOOL BUS PICK UP! in a walking school district of Pleasantville!!! On a Cul-de-sac. Easy 5-minute walk to the Chappaqua Train station just 45 minutes to Grand Central Station. Park-like grounds, fostering freedom and adventure. Inside, cathedral ceilings and Red Oak hardwood floors elegance, comfort and style in a coveted Chappaqua location, minutes to Farmers market shops train and restaurants. 1 Car Attached Garage

$863,400 Active

249 Mill River Road Chappaqua, New York

4 Beds 2 Baths 2,100 SqFt 0.45 Acres

149 King Street offers a rare opportunity to live in downtown Chappaqua where restaurants, shops, playgrounds, farmers market, library, train, school and Starbucks are all within walking distance. This bright and pristine end unit townhome boasts a no step covered entry level which offers access to the garage, utilities, laundry and a den/playroom. The second level consists of an open living/dining area, a sliding glass door to a trek deck and a wood burning fireplace with a decorative mantle flanked by bookcases. The renovated eat-in kitchen has stainless steel appliances, quartz countertops, a tile backsplash and ample storage. On the upper level, in addition to a loft, there are two bedrooms with custom closets and two baths. Guest parking available in the complex. Don't miss this one...it will not last!

$820,000 Pending

149 King Street 15 Chappaqua, New York

2 Beds 3 Baths 1,925 SqFt 0.03 Acres

$629,000 Active

324 N Greeley Avenue Chappaqua, New York

2 Beds 2 Baths 1,608 SqFt

Chappaqua, N.Y.

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