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:

1906 Grandeur. 2026 Luxury: The Ultimate Gated Sanctuary. Perched majestically atop a private hilltop, this gated 7,800-square-foot, five-bedroom estate presents a rare convergence of Gilded Age prestige and contemporary luxury. Believed to have been commissioned in 1906 for railroad magnate A.H. Smith, the residence has been masterfully renovated to honor its historic soul, featuring original interior stone walls and soaring ceilings that strike a perfect balance between grand scale and intimate warmth.Anchored by three distinctive hearths, the home is designed for both elegant living and everyday ease. A sun-drenched chef’s kitchen showcases a central island, dramatic overhead skylight, and professional-grade appliances. Unique architectural moments—including a circular-skylit Stargazer’s Nook—add character and charm, while the versatile five-bedroom layout offers both a magnificent two-story primary wing and a coveted first-floor private suite.Set on more than four exceptionally private acres, the grounds unfold as a true outdoor sanctuary, featuring a beautiful pool and spa (32x20), refined pergola terraces ideal for entertaining, and a private tennis court. From its commanding hilltop position, the estate delivers an unparalleled sense of privacy, security, and timeless elegance. Welcome home!

$4,500,000 Active

150 Old Farm Road N Chappaqua, New York

5 Beds 7 Baths 7,608 SqFt 4.45 Acres

Timeless elegance meets exceptional craftsmanship in this spectacular brick and stone estate, privately set behind gates on 4+ acres in one of Chappaqua's prestigious Whippoorwill neighborhoods. Designed by acclaimed architect Carol Kurth and masterfully built in 2003 by renowned builder Robert Torre, this extraordinary 5-bedroom, 6 full, 1 half bath residence offers over 10,000 square feet of impeccably crafted living space, where timeless architecture, luxurious finishes, and modern comfort come together seamlessly. A long private drive leads to a grand arrival. Inside, a dramatic two-story foyer with a sweeping circular staircase sets the tone for the home's impressive scale and refined design. Every room features soaring 10-ft ceilings, while the entry foyer and formal living room rise to over 20 feet, filling the home with light and volume. Rich hardwood floors, exquisite custom millwork, recessed lighting, and four fireplaces enhance the warmth and sophistication throughout. Designed for both grand entertaining and comfortable everyday living, the main level flows effortlessly from room to room. A spectacular formal living room with walls of windows opens to a gracious dining room, while the designer chef's kitchen features custom cabinetry, honed natural limestone floors, an oversized island with seating, breakfast area, abundant prep space, and premium stainless appliances including a 48" Wolf range, 30" Wolf convection oven, Thermador microwave, separate 36" Sub-Zero refrigerator and freezer, and 2 Bosch dishwashers. A butler's pantry enhances entertaining, and French doors lead to an expansive stone terrace overlooking the pool and grounds. Adjacent to the kitchen, the family room is anchored by a striking stone fireplace. The 1st floor also includes a spacious guest suite with a private bath, a back hall with pool bath, and access to the heated epoxy-finished three-car garage with room for up to five vehicles using lifts—a dream for the automobile enthusiast. Between 1st and 2nd floors is a private office and below a wine tasting room. The luxurious primary suite offers a dressing room, two oversized walk-in closets, a private balcony overlooking the backyard, and a spa-inspired bath with radiant heated floors, whirlpool tub, and steam shower. Three additional en-suite bedrooms, an expansive recreation room, and a 2nd floor laundry complete the upper level, while an additional 1st floor laundry room adds convenience. An enormous unfinished lower level offers exceptional potential for a home theater, fitness center, wine cellar, golf simulator, or additional recreation space. The outdoor setting is equally impressive. Beautifully landscaped grounds designed by acclaimed landscape architect Louis Fusco feature sprawling level lawns, specimen plantings, curated gardens, classic stone walls, and a magnificent Cardillo saltwater pool with a new filtration system and electric safety cover. An expansive stone patio and charming gazebo provide exceptional spaces for entertaining and relaxation. Bordering the Glazier Arboretum and backing to forever protected land, the property enjoys extraordinary privacy, tranquility, and picturesque natural surroundings. Additional amenities include a whole-house generator, electric vehicle charger, Elan smart home system for lighting, thermostats, and security. Just minutes from downtown Chappaqua, award-winning schools, and Metro-North for an approximately 50- minute commute to Manhattan, this remarkable Whippoorwill estate represents a rare opportunity to own one of Chappaqua's premier luxury properties.

$3,599,000 Coming Soon

301 Whippoorwill Road Chappaqua, New York

5 Beds 7 Baths 10,594 SqFt 4.39 Acres

Timeless elegance meets relaxed country chic at this extraordinary Chappaqua retreat. Ideally situated on one of Chappaqua's most coveted streets, this remarkable residence was originally built in 1910 and completely renovated and reimagined in 200l and then again in 2009 for modern living. Privately set amid beautifully landscaped grounds, 40 Algonquin blends classic country manor-style architecture with warm sophistication and resort-inspired outdoor living.A stately columned facade creates a striking first impression, while inside, expansive rooms, oversized windows, and sun-filled spaces create a bright yet inviting atmosphere throughout. Thoughtfully designed living spaces offer effortless flow for both relaxed everyday living and entertaining. This 4-bedroom home lives like a 5-bedroom, offering outstanding flexibility for guests, au pair, home office, or multigenerational living.Light-filled gathering spaces include a gracious den/library anchored by a fireplace, formal living room and an expansive family room with wood plank flooring and its own custom wood framed fireplace thoughtfully designed for comfortable living and effortless entertaining The beautifully updated chef’s kitchen is truly the heart of the home, featuring a redesigned center island, stainless steel appliances, and its own wood burning fireplace. The kitchen flows seamlessly into a stunning sun-filled dining area framed by a dramatic wall of windows overlooking the expansive outdoor terrace — creating the perfect setting for both everyday meals and memorable gatherings.A private main-level guest suite with en-suite bath adds wonderful convenience and flexibility for visitors or extended stays.Upstairs, A generously sized bedroom with en-suite and office/den flex space that lead to the tremendous primary suite retreat, complete with fireplace, dual bathrooms, two oversized walk-in closets, and a separate office or flex space with balcony to have your morning coffee. The third level offers an additional bedroom with loft/gaming area with full bathroom and an additional storage/Flex space.The renovated lower level adds impressive lifestyle space with a private gym, updated full bath, and beautifully finished recreation area ideal for entertaining, play, or relaxation. Walk-out directly to the patio where the Salt-water pool and hot tub create the ultimate outdoor retreat.The backyard is truly spectacular — a private resort-like oasis featuring a gorgeous gunite pool and spa, sprawling lawns, mature specimen plantings, multiple lounging and dining areas, and incredible privacy. Designed for both entertaining and peaceful retreat, the outdoor spaces deliver the lifestyle today’s luxury buyers are seeking.Ideally located just minutes to town, train, and Chappaqua Central School District award-winning schools, 40 Algonquin offers the rare combination of timeless charm, modern comfort, and elevated estate-style living- all in one of Westchester's most coveted settings.

$3,389,000 Active

40 Algonquin Drive Chappaqua, New York

4 Beds 7 Baths 5,563 SqFt 1.53 Acres

Exciting all new construction by highly regarded local builder, Tavo Development, along with noted architect Teo Siguenza, aiming for a Fall 2026 completion. This refined, 5,712 sq ft Colonial blends classic architecture with sophisticated modern living. The light-filled main level, with 10’ ceilings, offers a seamless open floorplan featuring a chef’s kitchen with island and service pantry, breakfast room with terrace access, formal dining room, private library, and an inviting family room with fireplace. A dramatic two-story entry foyer, generous mudroom with laundry, and attached 3-car garage complete the level. Upstairs, the luxurious primary suite is a true retreat, highlighted by a vaulted ceiling, fireplace, dressing room with island, and a spa-inspired dual bath with soaking tub and oversized shower with separate entries. Three additional ensuite bedrooms and a second laundry provide comfort and functionality. Nearly one acre of usable grounds, with town approved pool site, creates the ideal backdrop for the finest outdoor living. Next to 2026 new build by Tavo, in the Chappaqua school district. Convenient to town, schools, highways, and approximately 50 minutes to NYC. House has a 5 bedroom septic system.

$3,350,000 Pending

201 Bedford Road Chappaqua, New York

4 Beds 7 Baths 5,712 SqFt 0.94 Acres

Nestled in breathtaking natural surroundings, this modern architectural masterpiece by renowned designer Myron Goldfinger offers three levels of striking contemporary design. The residence features a soaring three-story curved ceiling, a dramatic floating staircase, and expansive open-plan living and entertaining spaces that frame the home’s private setting. The main-level primary suite provides a serene retreat, while the sleek, state-of-the-art kitchen is ideal for both everyday living and entertaining. Additional highlights include a fitness room, Shoreline pool with cabana, and a private tennis court. A 4+ car attached garage and below-ground oil heating add convenience. Located just 45 minutes from New York City, this one-of-a-kind residence blends luxury, privacy, and timeless modern design.

$2,990,000 Active

20 Bessel Lane Chappaqua, New York

6 Beds 6 Baths 8,200 SqFt 4.11 Acres

$2,895,000 Active

39 Barnes Lane Chappaqua, New York

4 Beds 6 Baths 4,589 SqFt 1.06 Acres

Welcome to this timeless and stunning Colonial, sited on 1.3 beautifully landscaped, private acres. This gracious 4-Bedroom Colonial blends classic architectural details with modern amenities -- open renovated kitchen with large island w/seating, spa-like bathrooms, new windows, solar paneling, Sonos throughout, a 2-bedroom cottage over the garage for long term guests, and a stunning Shoreline pool with new pool filter and heater. Hardwood floors, walls of new windows, stunning millwork create a warm and inviting setting -- and the renovated chef's Kitchen is a showstopper. The main floor features formal and informal gathering areas with wood-burning or gas fireplaces, a newly renovated eat-in Kitchen, spacious Mudroom with Laundry area and storage, Den/Sitting area with access to the pool + back yard, a delightfully bright Home Office with custom built-in cabinetry, a wonderful Great Room with wood burning fireplace that accesses the pool and back yard and a generous-sized Dining Room with wood-burning fireplace for friends to gather. Upstairs, the Primary Suite has a newly renovated spa-like Bathroom with two vanities, steam shower and soaking tub. Three additional bedrooms and two renovated Baths complete the upstairs. Above the two-car garage (with electric car charger) is another living space -- including 2-bedrooms, sitting area, Kitchenette and a screened-in porch. The property is sublime. Flat, manicured lawns, landscaped flowering trees + shrubs and a beautiful outdoor patio all center around the Shoreline pool. A true focal point for this incredible home.

$2,750,000 Pending

7 Quaker Lane Chappaqua, New York

6 Beds 5 Baths 5,004 SqFt 1.3 Acres

Tucked away on over two exquisitely landscaped acres in one of Chappaqua’s most prestigious enclaves, this exceptional newly constructed modern home redefines luxury living through a masterful blend of architectural sophistication, cutting-edge efficiency, and timeless elegance. Designed with a discerning eye and crafted with uncompromising quality, this magazine-worthy residence offers the ultimate turnkey lifestyle only moments from downtown Chappaqua, Metro North, and top-ranked schools. A dramatic arrival sets the tone as you enter through oversized custom doors into sun-drenched interiors framed by soaring 10-foot ceilings, expansive walls of glass, and wide-plank white oak flooring throughout. The home’s seamless open-concept design was thoughtfully curated for both grand-scale entertaining and intimate everyday living, creating a warm yet elevated atmosphere in every room. At the heart of the home is a spectacular chef’s kitchen worthy of a luxury design showroom, featuring premium professional-grade appliances, bespoke custom cabinetry, oversized quartzite island, designer lighting, and exceptional prep and storage space. Flow effortlessly into the breathtaking great room anchored by a statement fireplace and oversized sliders that open to a covered outdoor lounge, creating a true indoor-outdoor living experience. The primary suite is a private sanctuary rivaling a five-star resort, complete with a boutique-inspired dressing room and a spa-caliber bath featuring radiant heated floors, custom marble steam shower, soaking tub, and designer vanities. Generously sized ensuite bedrooms provide exceptional comfort and privacy for family and guests alike. The fully finished walk-out lower level elevates the home even further, offering an extraordinary extension of living space ideal for a private wellness retreat, gym, media lounge, golf simulator, wine tasting room, or entertainment venue. A striking custom wine display serves as a dramatic focal point and conversation piece. Every inch of this residence reflects a commitment to luxury and modern convenience, including geothermal heating and cooling, smart-home integration, premium fixtures and finishes, oversized heated garage space, and meticulously curated landscaping designed for both beauty and privacy. A rare offering that blends modern elegance, privacy, and convenience just under an hour from Manhattan. Come see a flawless fusion of contemporary design, superior craftsmanship, and effortless luxury set within one of Westchester’s most coveted communities today.

$2,699,000 Active

40 Hamilton Drive Chappaqua, New York

4 Beds 5 Baths 5,918 SqFt 2.263 Acres

Welcome to an exceptional move-in ready home located in a highly desirable Chappaqua neighborhood known for its award-winning schools & sought-after lifestyle. Perfectly positioned at the end of a quiet cul-de-sac, this stunning & chic property offers privacy, space & luxury living at its finest. Step inside & you'll find a bright, open-concept floor plan with natural light & high-end finishes throughout. The eat-in gourmet stylish kitchen is a chef's dream, complete with stainless steel appliances, custom cabinetry & a large center island - perfect for entertaining or everyday living. The inviting living room & elegant dining space provide a seamless flow, ideal for gatherings of any size. The upstairs boast 5 spacious bedrooms, including a luxurious primary suite compete with spa-inspired bathroom, oversized shower, & two generous walk-in closets. Four additional bedrooms provide flexible living, including a convenient jack & jill bathroom - optimal for family or guests. The noteworthy fully finished lower level offers additional living space with a large family room, private office & home gym - perfect for the current style of living. Outside, step into your own private resort-style oasis designed for ultimate outdoor living, featuring an in-ground gunite saltwater pool with an electric cover, a spacious patio with fire pit and built-in grill w/refrigerator. You will also enjoy a large flat yard with and existing vegetable garden. Additional highlights include fully owned energy-efficient solar panels & thoughtful upgrades throughout, including a convienent doggy door making this home as practical as it is luxurious. Whether you're a first time home buyer or upgrading, this is a rare opportunity to own a turn-key home in one of Westchester's finest communities. Come visit today!

$2,650,000 Pending

3 Pondfield Drive S Chappaqua, New York

5 Beds 5 Baths 4,975 SqFt 1.08 Acres

Set on beautifully landscaped grounds in one of Chappaqua’s most coveted neighborhoods, this exceptional luxury Colonial blends timeless architecture, designer finishes, and an unmatched indoor-outdoor lifestyle within the award-winning Chappaqua school district. Privately positioned against acres of preserved land, this premier Westchester County property offers both tranquility and convenience, just minutes to Metro North, downtown Chappaqua, and Chappaqua Crossing featuring Whole Foods Market and Life Time. Living like a 5-bedroom home, this luxury home for sale in Chappaqua showcases exceptional craftsmanship throughout with Juliet balconies, copper-topped cupolas, Belgian block-lined driveways, soaring ceilings, custom millwork, and walls of glass that flood the interiors with natural light. A dramatic curved staircase welcomes you into elegant yet comfortable living spaces designed for both everyday living and sophisticated entertaining. The chef’s kitchen is beautifully appointed with premium Wolf and Sub-Zero appliances, custom cabinetry, and European mosaic tilework, seamlessly connecting to the formal and casual gathering spaces. Highlights include a sophisticated library with gas fireplace, a stunning vaulted family room, and an impressive entertainment lounge with a wood-burning fireplace, wet bar, Viking wine refrigerator, and custom built-ins. The luxurious primary suite offers a gas fireplace, oversized dressing room, and spa-inspired bath, delivering the ultimate private retreat.Outside, the property lives like a private resort with a heated saltwater pool, outdoor fireplace, expansive patios, built-in grill, fire pit, poolside grotto with shower and changing area, gazebos, and a half basketball court with spotlighting. This exceptional Chappaqua estate offers luxury living, privacy, and resort-style amenities in one of Westchester’s most sought-after communities, known for top-rated schools, vibrant downtown, and easy NYC commute. A rare opportunity to experience estate-style living and the quintessential Chappaqua lifestyle at its finest.

$2,499,000 Active

33 Greenbriar Drive Chappaqua, New York

3 Beds 4 Baths 6,115 SqFt 0.93 Acres

Beautifully appointed and meticulously maintained 4 bedroom, 4 1/2 bath Colonial set on a level acre at the end of a quiet cul-de-sac in prestigious Inglenook Farm in the coveted Byram Hills Schools. A grand and light-filled two-story entry welcomes you into this refined open layout home featuring 9-foot ceilings on 1st and 2nd levels, oak flooring, and custom moldings and trim throughout. Formal living and dining rooms lead to a Chef's eat-in kitchen with granite countertops, oversized island, stainless appliances and dining area. The kitchen opens to a spacious family room with wood burning fireplace and doors to an expansive deck overlooking the serene, park-like level backyard. A mudroom off the kitchen provides everyday convenience, and a separate back bonus/recreation room adds flexible space for work, play, or relaxation. Upstairs, the primary suite features a spa-like bath, dressing area, and oversized custom-outfitted closet. The finished legal walkout lower level includes a large recreation room, gym, full bath, and ample storage. Other highlights include a large laundry room, large walk-in pantry and a 3-car attached garage. Whole house generator. Located just minutes to the towns of Chappaqua and Armonk, in the Byram Hills School District and just 45 minutes from NYC, this home is not to be missed. TAXES BEING GRIEVED.

$2,475,000 Pending

17 Byram Meadows Road Chappaqua, New York

4 Beds 5 Baths 6,640 SqFt 1.02 Acres

A Rare Opportunity Where History Meets Modern Living.Built in 1750 and thoughtfully renovated in 2005. White clapboard, black shutters, cedar shake roof, and copper gutters set a timeless exterior, framed by professionally designed grounds.A wide entry hall opens to living and dining rooms bookended by floor-to-ceiling stone fireplaces. Hardwood floors and detailed millwork mark the quality craftsmanship throughout every room.The main house offers four bedrooms and three and a half baths. The gourmet kitchen anchors daily life. Sub-Zero and Viking appliances, generous custom cabinetry, and a large center island flows into a family room that opens directly onto the patio and gardens.The primary suite is a retreat in its own right: vaulted ceilings, a stone fireplace, walk-in closet, and a spa-inspired bath with soaking tub and glass-enclosed shower.A separate carriage house extends the home’s character and livability. The main level offers a welcoming sitting room, while upstairs an open living area with kitchenette is bathed in natural light. Equally suited to hosting guests or serving as a private studio or work-from-home retreat. Outside, grounds designed by acclaimed landscape architect Jan Johnsen unfold around an oversized stone patio with outdoor kitchen, generous space for hosting friends, or enjoying the surrounding beauty in complete privacy. A vegetable garden and expansive lawn extend the property further, all bordered by protected land that offers a balance of openness and seclusion that can’t be replicated.A heated three-car garage rounds out the property. Byram Hills School District. Chappaqua train parking eligibility.

$2,350,000 Pending

790 King Street Chappaqua, New York

4 Beds 5 Baths 4,385 SqFt 1.7 Acres

Experience modern luxury at 21 Hemlock Hills, a stunning home set on 1.8 acres of meticulously landscaped grounds.This residence features 4 spacious bedrooms and 3.5 bathrooms, including a gorgeous, luxurious master bathroom that serves as a private retreat. The heart of the home is the Carol Kurth-designed Leicht kitchen, a masterpiece featured in a magazine, seamlessly flowing into the open great room—perfect for entertaining or everyday living.A dedicated home office provides a quiet and functional space, while the finished basement offers endless possibilities for recreation or additional living areas. The extensive landscaping creates a serene outdoor sanctuary, ideal for relaxation or hosting gatherings.Practicality meets elegance with the inclusion of a full-house generator, ensuring uninterrupted comfort and convenience. Every detail of this home has been thoughtfully curated, from its modern finishes to its functional layout, offering a harmonious blend of sophistication and practicality.Discover the perfect balance of style and comfort at 21 Hemlock Hills. Schedule your private tour today to explore this exceptional property.

$2,250,000 Pending

21 Hemlock Hills Chappaqua, New York

4 Beds 4 Baths 3,988 SqFt 1.81 Acres

Set on a picturesque property in sought-after Random Farms, this stunning 6-bedroom residence offers dramatic views, soaring ceilings, and exceptional living spaces designed for both everyday comfort and elegant entertaining. A breathtaking double-height entry welcomes you into sun-drenched interiors featuring walls of windows, rich hardwood floors, and seamless open-concept flow throughout.The spectacular great room is the heart of the home, highlighted by oversized architectural windows, a striking fireplace, and direct access to outdoor living spaces overlooking the serene landscape. The spacious chef’s kitchen features extensive custom cabinetry, premium appliances, large center island, and sunny breakfast area perfect for gathering.Designed with flexibility in mind, the home includes a full first-floor guest suite and a private first-floor office with custom built-ins — ideal for today’s work-from-home lifestyle. Additional highlights include elegant formal living and dining rooms, generous secondary bedrooms, and beautifully scaled entertaining spaces throughout. Located within the prestigious Random Farms community offering clubhouse, pool, tennis, and lifestyle amenities, this exceptional home combines privacy, luxury, and convenience just minutes to town, train, and top-rated Chappaqua schools.

$2,195,000 Pending

22 Random Farms Circle Chappaqua, New York

6 Beds 6 Baths 6,563 SqFt 1.21 Acres

Welcome to 350 Wooded Hill Court. A grand, young Colonial offering resort-style living in Chappaqua, sited on 2.9 acres. Discover the perfect blend of luxury, lifestyle, and location in this exceptional 4-bedroom, 4.5-bath set on a private cul-de-sac just minutes from town, schools, shopping, and Metro-North. Built with exquisite craftsmanship by one of Chappaqua’s most reputable builders, this home showcases superior quality, timeless detailing, and an open floor plan ideal for modern living. A striking two-story entry foyer sets the tone for the sun-filled interior, featuring Brazilian Cherry floors throughout, elegant millwork, and expansive windows framing views of the meticulously landscaped grounds. The gourmet chef’s kitchen offers top-of-the-line appliances, custom cabinetry, and seamless flow into the family room and sunroom, perfect for everyday living and entertaining. Upstairs, the luxury primary suite feels like a private retreat with a massive custom walk-in closet/dressing room complete with office space and a spa-inspired bath. Three additional spacious bedrooms and beautifully appointed baths complete the second floor. The lower level is an entertainer’s dream, featuring a state-of-the-art home theater, full wet bar, recreation space, and direct access to the yard. Step outside to your own private oasis. A breathtaking Gunite infinity-edge pool, charming gazebo, stone patios, stone walls, and specimen trees create a resort-like setting. Whether hosting summer gatherings or enjoying peaceful mornings outdoors, this property delivers unmatched indoor-outdoor living. Additional highlights in • Full-house generator • 3-car attached garage with 2 charging stations• Newer roof. Award winning Yorktown Schools.

$2,100,000 Pending

350 Wooded Hill Court Chappaqua, New York

4 Beds 5 Baths 4,681 SqFt 2.9 Acres

Perfectly situated on over three picturesque acres, this timeless 5 bedroom Federal Colonial effortlessly blends historical charm with modern convenience. Thoughtfully updated while maintaining its classic character, the home offers expansive living spaces, refined finishes, and an exceptional layout designed for today’s lifestyle. At the heart of the home is the stunning chef’s kitchen featuring a Wolf 6-burner range with grill and double ovens, Sub-Zero refrigerator, custom maple cabinetry, large banquette and oversized island — all seamlessly opening to the dining room and dramatic great room, ideal for both everyday living and entertaining. A charming screened-in “lemonade porch” invites peaceful mornings and relaxed summer evenings overlooking the beautiful property. The home offers a flexible and functional floor plan featuring a private first-floor guest suite, separate office spaces, and, upstairs, a quaint secondary bedroom wing accented with irreplaceable wide plank floors. For added privacy, the expansive primary suite can be accessed via a secondary staircase. The luxurious primary retreat features a spa-like bath and oversized his and hers walk-in closets, creating a true sanctuary. Outside, enjoy resort-style living with a heated Gunite pool, expansive upper and lower patios, sweeping lawns, a very special Williamsburg style potager, and mature landscaping — all offering incredible usable outdoor space rarely found in the area. There’s even room for a future tennis or pickleball court. Located in the highly sought-after Byram Hills School District with convenient access to Chappaqua train parking, downtown shops, restaurants, and local favorites, this exceptional property offers the perfect balance of privacy, charm, and everyday convenience — all with low taxes.

$1,999,999 Pending

765 King Street Chappaqua, New York

5 Beds 5 Baths 4,058 SqFt 3.46 Acres

Nestled on over an acre of beautifully landscaped grounds in the highly sought-after Chappaqua School District, this exceptional residence offers a rare blend of privacy, craftsmanship, and versatility. Behind a gated entrance, mature specimen plantings, expansive lawns, and a tranquil natural setting create a true private retreat just minutes from downtown Chappaqua and Metro-North.Thoughtfully improved throughout the years, the home features cedar siding, Anderson windows and sliding doors, custom hardwood flooring with intricate inlay detail, reinforced structural beams, remote-controlled skylights, and numerous mechanical upgrades. Dramatic ceilings, walls of windows, and sun-drenched living spaces create an inviting atmosphere designed for both everyday living and entertaining.The eat-in kitchen is appointed with custom cabinetry, premium stainless steel appliances, a center island, and seamless access to the outdoor deck. Formal and informal living spaces flow effortlessly throughout the main level, highlighted by a dramatic living room with soaring ceilings, oversized windows, and a marble fireplace.The luxurious primary suite serves as a private retreat featuring custom California Closets and a stunning spa-inspired bath with a freestanding soaking tub, oversized glass-enclosed shower with body jets and bench seating, custom mahogany detailing, designer lighting, and exceptional finishes throughout. Renovated bathrooms throughout the home showcase custom tilework, premium fixtures, and thoughtful spa designs.Additional highlights include California Closets throughout, intercom and surround sound systems, smart gate access, surveillance cameras, irrigation system, renovated garage, and a charming detached storage shed. Outdoor living is equally impressive with expansive decking, a remote-controlled SunSetter awning, and peaceful grounds designed for entertaining and relaxation.A truly special offering combining privacy, quality craftsmanship, modern conveniences, and exceptional flexibility in one of Westchester County's most desirable communities.

$1,998,999 Active

4 Old House Lane Chappaqua, New York

4 Beds 4 Baths 3,124 SqFt 1.322 Acres

Exquisite architectural design, timeless charm & luxurious modern amenities merge effortlessly in this elegant Colonial in the heart of Chappaqua. C.1902 & superbly upgraded and meticulously maintained, the home offers an open, sun-bathed interior w/hardwood floors, high ceilings, abundant built-ins, extensive millwork and a quintessential porch - sure to please the most discerning buyers! The gracious foyer leads to a classic dining room with fine millwork, a fireplace and boasts a lovely historical handpainted mural of the Hudson Valley at the turn of the century. The formal living room with concealed pocket doors has a second fireplace and French doors opening to the covered porch. The sunny and bright eat-in kitchen is a chef’s dream featuring a Wolf double oven, Sub Zero fridge, ample storage and opens to the casual living room/ leisure room. 2nd floor features a primary bedroom suite with a sparkling spa bath, walk-in closet and and adjoining office. An additional 3 bedrooms and a tastefully renovated hall bath complete the second floor. Finished 3rd level includes a bedroom and Bonus room perfect for studio/office/playroom w/ full hall bath. The large unfinished basement offers additional space and Bilco doors to the exterior. A 2 car detached garage originally used as stables has 2 levels and offers many possibilities. The park-like, level property is professionally landscaped and is an oasis of tranquility w/ lush lawns, a dazzling variety of specimen trees & plantings with ample parking. Ideally located close to town, train, schools and more!

$1,975,000 Pending

111 Prospect Drive Chappaqua, New York

5 Beds 4 Baths 4,166 SqFt 0.67 Acres

Welcome to this warm, inviting 5-bedroom home nestled on a tree-lined beautiful Chappaqua street. It has a lovely front porch with plenty of room for cozy chairs, perfect for sipping coffee in the morning. Inside, there is a spacious living room with a wood burning fireplace, a bright kitchen and a large island. First floor features a Primary Suite, 4 additional bedrooms with 2 full baths upstairs as well as two offices.There is a large finished basement that runs the length of the house with an additional full bath. The charm really comes through in the details- wood floors, perfect layout, wood built -ins and big windows letting in lots of light. It’s the kind of home and neighborhood you just fall in love with.

$1,925,000 Pending

1 Hitching Post Lane Chappaqua, New York

5 Beds 5 Baths 4,489 SqFt 1.96 Acres

Welcome to 2 DeWitt Drive — a stunning 2025-built carriage home offering refined luxury and effortless living in one of Chappaqua’s most desirable communities. This light-filled corner residence spans 3,574 square feet with 2 spacious bedrooms (lives like a 3BR) and 3.5 baths, thoughtfully designed with high-end finishes and sophisticated upgrades throughout. Expansive windows flood the home with natural light and showcase the beautiful grassy expanse bordering the front and side of the property, creating an airy, open feel rarely found in attached living. The main living spaces blend elegance and comfort with designer details, premium materials, and a seamless flow. The generous primary suite offers a true retreat, while flexible bonus spaces provide room for multiple home offices, media room, or guest accommodation. Enjoy warm-weather living on the expansive second-floor terrace with beautiful open views, or relax on the inviting front porch overlooking the generous grassy lawn right at your feet. This home delivers the best of new construction without the wait. Residents enjoy exclusive access to a private clubhouse featuring a beautifully appointed common area, fitness center, and pool. Located within the Chappaqua School District and set in a vibrant mixed-use community with Whole Foods, Starbucks, Restaurants and Shopping just moments away, this property offers a rare combination of luxury, convenience, and lifestyle. A sophisticated, low-maintenance opportunity in the heart of Chappaqua.

$1,799,000 Pending

2 Dewitt Drive Chappaqua, New York

2 Beds 4 Baths 3,574 SqFt 0.1 Acres

Welcome to 26 Wallace Way — a standout residence in the coveted, sold-out Chappaqua Crossings Carriages community. Thoughtfully designed and impeccably finished, this first-floor primary bedroom home elevates townhouse living with refined interiors, dramatic architecture, and a setting that is both private and connected.The main level makes an immediate impression with a dramatic double-height living room, where oversized windows flood the space with natural light and tranquil views of the open grass courtyard placing the home at the heart of one of the community’s most desirable locations. The chef’s kitchen flows seamlessly into the living and dining areas, anchored by a generous center island, custom cabinetry, and premium appliances, creating an ideal layout for both everyday living and entertaining. The primary suite offers effortless main-level living, complete with a spa-inspired bath and an expansive walk-in closet. A stylish powder room, along with thoughtful storage, laundry, and garage access, completes the level.Upstairs, a sunlit loft serves as a versatile lounge or gathering space with western exposure showcasing beautiful sunsets beyond. From here, step out to the private outdoor terrace overlooking landscaped grounds and treetops—a peaceful retreat perfect for morning coffee or evening unwinding. This level also features a well-appointed second bedroom, a full bath, and a dedicated home office, along with large walk-in closets that enhance both comfort and functionality.The living space extends even further with a finished basement, ideal for an additional bedroom, media room, or gym, and is complemented by a third full bathroom. The home also includes dedicated areas on all three levels for a future elevator, offering long-term flexibility and ease of living.Just a short walk from the clubhouse and pool, the amenities feel like a natural extension of your home. Residents enjoy walkable access to the fitness center, Whole Foods, Life Time, shops, and restaurants, along with a dedicated shuttle to the train for effortless commuting.Built by Toll Brothers, known for exceptional quality and craftsmanship, 26 Wallace Way offers a rare blend of first-floor primary living, dramatic architectural design, privacy, and resort-style amenities in one of Chappaqua’s most sought-after communities.

$1,780,000 Pending

26 Wallace Way Chappaqua, New York

2 Beds 4 Baths 2,945 SqFt 0.06 Acres

Renovated and Reimagined Colonial on Spectacular Park-Like Grounds, this exceptional residence includes a separate cottage-style bonus building that offers endless possibilities. Whether envisioned as a private home office, artist’s studio, wellness retreat, yoga or fitness center, man cave or an inspiring creative workspace, this detached structure provides exceptional flexibility and privacy. Nestled amid the lush grounds and mature landscaping, it serves as a peaceful extension of the home and creates a rare opportunity for today’s work-from-home lifestyle or entrepreneurial pursuits. At the heart of the home, an original stone wood-burning fireplace serves as a stunning focal point, infusing the living space with warmth, character, and timeless charm. Perfect for cozy winter evenings, holiday celebrations, and memorable gatherings with family and friends, this impressive architectural feature creates an inviting atmosphere that embodies the true spirit of home. The stunning chef’s kitchen features premium stainless-steel Thermador appliances, elegant quartz countertops, a spacious walk-in pantry, and seamless access to an oversized slate patio—ideal for indoor-outdoor entertaining. The captivating primary suite offers soaring beamed ceilings, a generous sized walk-in closet, and a luxurious spa-inspired bath complete with dual vanities and a classic clawfoot soaking tub. Convenient second-floor laundry with storage enhance everyday living. Additional highlights include all-new Anderson windows, all new electrical, all new plumbing, new roof, new c/air, new Navien system, energy-efficient blown-in insulation, solid wide-plank oak flooring, and exquisite custom millwork throughout. The separate cottage building has all new electrical, blown insulation, windows, flooring and roof. Located minutes from the Metro North Train Station and downtown Chappaqua, you'll have quick access to commuter routes and a charming village filled with shopping, restaurants and community events. A rare offering that perfectly blends timeless charm with sophisticated modern updates, all set within a serene and private setting designed for both relaxation and entertaining.

$1,695,000 Active

676 Hardscrabble Road Chappaqua, New York

3 Beds 3 Baths 2,420 SqFt 1.483 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

Most “walk-to-town” homes ask you to compromise on space, privacy, or both. At 14 Crossways, you get all three. Set less than a mile from the Chappaqua station, it combines true walkability with more than 3,100 square feet of well-organized living space on a private, level half-acre. Carefully maintained and thoughtfully improved, it is also a house designed for entertaining. At its center, the kitchen acts as the engine room of the home, anchored by a substantial island and flowing directly into the family room, dining room, and screened porch. Because the porch is accessed from the kitchen, the connection between indoor and outdoor living feels particularly natural and highly practical. From the family room, the house also connects directly to the lower level, allowing the living spaces to expand easily when people spread out. The first floor also includes a dedicated office and a separate guest bedroom with a full bath, positioned to function independently from the main living areas. Upstairs, the nearly 600 square foot primary wing is set apart, offering a true sense of scale and separation, along with a walk-in closet and primary bath. Two additional bedrooms and a full bath are located on the opposite side, creating a balanced and practical second floor. The lower level adds a large recreation room, a powder room, and a custom wine cellar, giving the house a valuable secondary entertaining space that is fully integrated into the overall layout. A rare combination of scale, function, and convenience in the heart of Chappaqua.

$1,600,000 Pending

14 Crossways Chappaqua, New York

4 Beds 4 Baths 3,138 SqFt 0.51 Acres

Thoughtfully reimagined farmhouse with barn, this distinctive 4-bedroom, 3-bath home blends historic charm with striking modern design. Set on close to 2 private acres surrounded by mature trees, the property offers exceptional privacy and a peaceful natural setting. Inside, soaring ceilings, oversized windows, and multiple skylights flood the home with natural light. The open-concept living space flows seamlessly into a sleek contemporary kitchen featuring custom cabinetry, a large center island, premium appliances, and walls of glass that connect the interior to the surrounding landscape—ideal for both everyday living and entertaining. Solar panels enhance the home’s efficiency, adding a thoughtful, sustainable element to its modern design. The home offers four well-proportioned bedrooms and three beautifully designed full baths, including a serene primary suite with a spa-like bath featuring a soaking tub and double vanity. A versatile loft area provides flexible space for a home office, guest quarters, and more.The sun-filled lower level with expansive picture windows creates an inviting lounge or media space and includes a lovely, newly renovated laundry room with a hot stone sauna.A rare blend of modern architecture, farmhouse warmth, sustainability, and privacy on close to two acres in Chappaqua.

$1,599,999 Pending

734 King Street Chappaqua, New York

4 Beds 3 Baths 3,672 SqFt 1.93 Acres

Welcome to 34 Turner Drive South -- an expanded and gracious 4-bedroom, 2-1/2 Bath, Farmhouse Colonial nestled at the end of a private drive. This special home is set on over an acre of flat, private property, surrounded by towering trees and tranquil woods. The interior features 3 fireplaces, custom millwork, hardwood floors and classic architectural details. The main level has a gracious Living Room w/wood-burning fplc, Dining Area that opens to large Family Room w/built-ins, gas fplc and French doors out to a wonderful, expansive screened-in porch; Kitchen w/large eat-in area, a third fplc and doors out to screened-in porch; Office and Powder Room. Upstairs you will find a generous-sized Primary Bedroom Suite w/large Bath and walk-in closets, three additional Bedrooms, recently renovated Hall Bath and Laundry. New Roof (2023), New Furnace (2022) and new Marvin windows throughout. A truly exceptional home.

$1,599,000 Pending

34 Turner Drive Chappaqua, New York

4 Beds 3 Baths 3,496 SqFt 1.36 Acres

A truly exceptional offering, this picture-perfect 1930s Colonial blends timeless elegance with modern luxury. Set on beautifully landscaped property in a serene setting yet just a moment away from town. Impeccably maintained, tastefully expanded & renovated, the home showcases refined design, effortless flow, and enduring architectural charm.The main level is thoughtfully designed with a spacious, open layout—ideal for both everyday living and entertaining. A welcoming foyer opens to a gracious living room with a fireplace and the oversized window frames the view to the back yard. The dining room flows seamlessly into the beautifully appointed chef’s kitchen, complete with a 48-inch Wolf range, Sub-Zero refrigerator, quartzite countertops, custom cabinetry, and a generous center island. Just off the kitchen, the family room offers a warm and comfortable setting for relaxing or casual gatherings. The versatile sunroom, with walls of windows and a slider to the patio is well suited for a sitting room, an office, or a play room. A mudroom with custom built-in storage, a separate laundry room, and a stylish powder room enhance the home’s effortless, well-curated lifestyle.Upstairs, this 3-bedroom home lives like a 4-bedroom, offering exceptional flexibility. The expansive primary suite is a private sanctuary with abundant natural light, a spa like bath with soaking tub, separate shower, private water closet, dual vanities, and a dressing area with two walk-in closets. Two additional bedrooms, a full bath, and an office complete the second floor.Outside the property it truly magnificent—lush, level lawn framed by mature landscaping and specimen plantings create a rare sense of privacy and tranquility . A spacious patio extends the living space outdoors, perfect for dining, entertaining, or simply unwinding while enjoying the peaceful surroundings. Ideally located just moments from town, the train and schools, this home offers an exceptional blend of timeless elegance, modern comfort, and unmatched convenience.

$1,599,000 Pending

40 Kings Court Chappaqua, New York

3 Beds 3 Baths 3,121 SqFt 0.32 Acres

Enter into this enduring Colonial blending elegance with today's lifestyle. This home lives like a 4-bedroom and has 4 BR septic. Set on beautifully landscaped property moments away from town, the train and Chappaqua schools. Tastefully expanded and renovated in 2008, this home showcases classic architectural details everywhere. A welcoming foyer opens to a gracious living room and fireplace. A formal dining room with a tray ceiling. Timeless appointed chefs EIK with Wolf appliances, custom cabinetry and marble counter tops, wine refrigerator and breakfast bar. The family room offers a second fireplace and a wall of windows to view the private setting. The sunroom offers custom built-ins and an abundance of natural light. A first floor study/bedroom and full bathroom works well for guests or an au pair. A mudroom with custom built-ins. Upstairs is the primary bedroom with high ceilings, walk-in custom closet, private study, and en-suite bath with double sinks, marble shower and whirpool bath. Two additional bedrooms, one with custom built-ins, custom closets, and a hall bath. New laundry is located conveniently on the second floor. Outdoors, an expansive deck extending the living space and creating the perfect setting for entertaining, dining and relaxing while overlooking mature landscaping and private grounds that back up to protected green space. Completing the property is a detached two car-garage with generous storage above. The home was extensively renovated and expanded in 2008 offering the finest architectural finishes. An exceptional offering. New roof 2024 and new 4 bedroom septic 2026.

$1,590,000 Active

131 Douglas Road Chappaqua, New York

3 Beds 3 Baths 2,690 SqFt 0.7 Acres

Welcome to this sophisticated carriage home at 17 Lila Lane, offering a rare blend of contemporary luxury and maintenance-free living within the prestigious Chappaqua Crossing community. The thoughtfully designed layout is anchored by a gorgeous chef’s kitchen, featuring a large center island with ample seating and a premium JennAir appliance package. Equally enticing is the coveted first-floor primary suite, providing a serene sanctuary with a spa-inspired ensuite bathroom and an expansive walk-in closet. The second level serves as a versatile retreat, home to a spacious second bedroom, a dedicated home office/bedroom, an inviting sitting area, and a gorgeous private terrace. Additional living space abounds in the fully finished lower level, perfectly suited for a high-end home gym and a cozy media den, while the attached two-car garage comes equipped with an EV charging station for modern convenience. Residents enjoy an unparalleled "village within a village" lifestyle defined by sprawling green space and scenic walking trails, with exclusive access to a luxury clubhouse and sparkling pool. Situated in the heart of Chappaqua, this residence is just steps from Whole Foods, Life Time Fitness, delicious restaurants, and offers the convenience of a private community shuttle to the Metro-North for a seamless commute to Manhattan.

$1,590,000 Active

17 Lila Lane Chappaqua, New York

3 Beds 4 Baths 2,576 SqFt 0.06 Acres

Set on a sought-after cul-de-sac lined with charming classic homes, this 1938 Colonial masterfully blends period charm with today’s lifestyle needs. Set on a lovely private acre with flat lawns surrounded by towering trees yet nestled in a neighborhood setting, this 2,715 square foot center hall Colonial home offers 4 bedrooms, 2 full and 2 half baths. The heart of the home is the family room open to the kitchen, featuring a raised hearth stacked stone fireplace, custom built-ins, and a door to the deck and patio. The eat-in kitchen is a chef’s dream, with tile flooring, a large center island, wood cabinetry, glass tile backsplash, and premium stainless steel appliances including a 6-burner Wolf gas range with addt'l griddle and grill, double ovens, and a Sub-Zero refrigerator — plus its own door to the deck. A screened porch offers additional space for indoor-outdoor living.Elegant formal spaces include a living room with fireplace and built-ins, and a dining room with built-in corner cupboards, both showcasing beautiful oak hardwood floors throughout. The primary bedroom suite is a true retreat, with an adjacent sunroom/home office, walk-in closet, and en-suite full bath. Three additional bedrooms and a hall bath complete the upper level.Additional highlights include main floor laundry, a side door entry, ample basement storage, and expansion potential over the garage. Recent updates include a roof just 8 years new, boiler (2015), new windows in the kitchen, family room, sunroom, and 2 bathrooms, 4-zone heat, 2-zone central air, and a portable generator hookup for peace of mind. Cedar shake exterior adds to the timeless curb appeal.Located in the award-winning Chappaqua school district, close to shops, schools and metro North commuter train, this is a rare opportunity to own a piece of classic Chappaqua charm with all the modern comforts today’s buyers demand.

$1,575,000 Active

50 Ludlow Drive Chappaqua, New York

4 Beds 4 Baths 2,715 SqFt 0.99 Acres

$1,550,000 Coming Soon

312 Quaker Road Chappaqua, New York

3 Beds 3 Baths 2,451 SqFt 0.51 Acres

Beautifully updated split ranch set on 1.02 park-like acres in a sought-after Chappaqua location near school, train and walkable to village center train and shops. The heart of this home is a spectacular high-end renovated eat-in kitchen featuring white cabinetry, Wolf, Miele, and Sub-Zero appliances, honed marble and granite counters, a center island with pendant lighting, a peninsula with seating, a walk-in pantry, bay window and a door to the patio-all flowing seamlessly into the living room with stacked stone fireplace, family room, and large dining area with bay window and crown molding. Wide-board pegged oak hardwood floors, crown molding and an abundance of natural light enhance the warm, inviting ambiance throughout.The living room showcases a dramatic floor-to-ceiling stacked stone raised hearth fireplace and custom built-ins. The light-filled family room impresses with soaring ceilings, a skylight, windows on three exposures, and French doors opening to a slate patio- perfect for indoor-outdoor living. A windowed main-level laundry room with built-ins and a renovated powder room add everyday convenience.Upstairs, are four bedrooms-three generous bedrooms with wide-board pegged oak floors and double closets share a newly renovated hall bath with double-sink vanity and full tub. A privacy door leads to the primary suite with king-size bedroom, oversized windowed walk-in closet, and an updated en-suite spa style bath with skylight, jetted tub, large storage vanity and frameless glass shower.The expansive lower level offers exceptional flexibility and has a playroom with sliding glass doors to a lower patio, home office, powder room, large mudroom, and an oversized two-car garage with storage alcove. The fenced backyard with multi-level patios and flat lawn presents a potential pool site. Additional features include new windows, professional landscaping, wired-for-generator, EV charger, closet organizers, 10-year new roof, 4 zone HVAC, and low taxes. Truly move-in condition, a gem, won’t last.

$1,495,000 Pending

105 Cross Ridge Chappaqua, New York

4 Beds 4 Baths 2,953 SqFt 1.02 Acres

Perched on a lushly landscaped acre and thoughtfully expanded, offering a comforting blend of function, space, and versatility for today’s lifestyle, whether working from home (the main-level office opens to a private deck, creating a delightful setting for morning coffee or an inspiring workday), entertaining (the spacious living room with fireplace adjoins the formal dining room with sliding glass door to the patio for easy alfresco dining; the bright eat-in kitchen is smartly designed with custom cabinetry and granite countertops, and a breakfast area with a big bay window and a French door to the patio for immediate access to outdoor cooking and entertaining), or simply enjoying room to spread out (an expanded family room, den/study/playroom/home office x 3, 3 spacious bedrooms, 4 full bathrooms [including 2 ensuite]), there’s a place for everyone to live, work and play. Versatility abounds in the expanded family room with its built-ins and spaces to recreate, work or relax. The luxurious primary suite features a soaring ceiling, oversized windows, boutique-like walk-in closet, and a spa-like bath with double vanity, soaking tub, and separate shower. The second bedroom also features a walk-in closet and an upscale, private ensuite bath with shower. The shared hall bath has been recently refreshed with a double vanity, sconces and mirrors, plus new tile and glass surrounding a bathtub with shower and handheld. The lower-level playroom enjoys easy indoor/outdoor access with a French door to the yard. Commandingly set on a pretty, landscaped acre with a large patio and terraced lawns adding to the scenic surroundings. Welcoming, comforting, spacious and versatile inside and out.

$1,399,000 Active

22 Garey Drive Chappaqua, New York

3 Beds 4 Baths 3,140 SqFt 1.007 Acres

Welcome to 10 North Lane, a spacious 3-bedroom, 3-bath home offering 3,155 square feet of comfortable living in the heart of Chappaqua. Located within the highly acclaimed Chappaqua School District, this charming residence is perfectly positioned on a quiet, private cul-de-sac street just minutes from the Taconic Parkway, shopping, and the vibrant Chappaqua town center. Enjoy a beautifully level yard, ideal for outdoor entertaining, play, or peaceful relaxation. Featuring updated hardwood floors, a convenient first-floor bedroom, and tasteful minor updates throughout, this home blends space, style, and serenity. A rare opportunity in one of Westchester’s most desirable communities!

$1,350,000 Pending

10 North Lane Chappaqua, New York

3 Beds 3 Baths 3,155 SqFt 1.1 Acres

Completely reimagined and move-in ready, this sun-filled 3-bedroom plus home office, 2.5-bath home sits on over one acre of rare, level property in one of Chappaqua’s most sought-after neighborhoods. Blending modern updates with timeless design, the home offers a bright, open flow ideal for today’s lifestyle, with expansive windows that flood every room with natural light.The main level showcases an expansive living room with a newly added gas fireplace and dual picture windows, a dedicated home office ideal for remote work, and a beautifully updated eat-in kitchen that flows seamlessly into an open-concept dining room —perfect for everyday living and entertaining. Step outside to a large deck overlooking the private, flat backyard, offering exceptional indoor-outdoor living. Just off the kitchen, a half-flight of stairs leads to a versatile ground level bonus room with picture windows, windowed powder room, and conveniently located mudroom with direct access to the attached two-car garage—ideal for everyday convenience. The second level, features a generous primary suite with a walk-in closet and en-suite bath, along with two additional spacious bedrooms and a full hall bathroom. The expansive lower level provides additional flexible living space, including a recreation room a windowed laundry room along with ample storage space.Set on meticulously maintained, park-like grounds with mature plantings, this property offers the perfect combination of tranquility and convenience. Just minutes to downtown Chappaqua, schools, train, Gedney Park, shopping, and dining!

$1,299,000 Pending

14 Garey Drive Chappaqua, New York

3 Beds 3 Baths 2,096 SqFt 1.2 Acres

$1,299,000 Pending

816 Hardscrabble Road Chappaqua, New York

3 Beds 3 Baths 2,444 SqFt 0.58 Acres

Set on a level .64-acre property along one of Chappaqua's most sought-after neighborhood streets, 9 Oak Hill Road is a beautifully updated 4-bedroom, 3-bath Raised Ranch that offers spacious, light-filled living in a peaceful natural setting. A covered front porch welcomes you into an entry foyer, where a short mezzanine staircase leads to the main living level. Here, a gracious living room with a picture window flows effortlessly into the adjoining dining room, creating an inviting space for everyday living and entertaining. Adjacent to the dining room, the eat-in kitchen completes the home's open, functional layout. Oversized windows at both the front and rear fill the living areas with natural light, while the property's exceptional setting—backing to the Saw Mill River Audubon Society's Cameron-Murfeldt Sanctuary—offers privacy, scenic views, and a charming pond that enhances the tranquil landscape.The eat-in kitchen is thoughtfully designed with white cabinetry, stainless steel appliances, a picture window, and a sun-filled breakfast area that enjoys morning light. A door opens directly to the deck, making outdoor dining and weekend barbecues effortless.Three well-proportioned bedrooms are located on the main level, including a spacious primary suite with two closets and a private bath. A corner bedroom enjoys windows on two sides, while the third bedroom features two front-facing windows and a generous double closet. Every bedroom in the home is outfitted with custom California Closets, providing beautifully designed, highly functional storage and organization.The finished walk-out lower level provides exceptional additional living space with a generously sized family room featuring hardwood floors, a decorative electric fireplace, and sliding glass doors that open to the patio. A private, expansive fourth bedroom with hardwood floors and a double closet, a full bath with shower, laundry area, utility room, abundant storage, and direct access to the attached two-car garage complete this versatile level. Set back from the road with a level driveway and expansive front lawn, this inviting home offers the perfect balance of comfortable living, effortless entertaining, and the peaceful beauty of its park-like surroundings.

$1,299,000 Active

9 Oak Hill Road Chappaqua, New York

4 Beds 3 Baths 2,406 SqFt 0.631 Acres

The truly enchanting waterfront setting of this exceptional in-town 1930 Dutch Colonial is defined by sweeping views, lush landscaping, expansive flat yards and a pristine spring-fed duck pond. Meandering stone pathways guide you through beautifully curated grounds, revealing peaceful gathering spaces and quiet corners perfect for enjoying the storybook scenery. Just off the kitchen, a generous stone patio creates an ideal backdrop for seamless indoor-outdoor entertaining; the front porch is a classic for your rocking chairs and morning coffee.The home blends timeless craftsmanship with modern comfort, featuring a stunning gourmet kitchen, elegant French doors, central air and so much more, thoughtfully designed for effortless everyday living.Perfectly positioned in the heart of the village of Chappaqua, with no need for a car to get to everything, you’re just moments from town, shops, restaurants, and the Metro-North train station, approximately 45 minutes express train to New York City. Located in one of Westchester’s most sought-after communities, Chappaqua is known for its fabulous schools, charming downtown, scenic wooded landscapes, and outstanding quality of life. Taxes with STAR approximately $20,556. A magical home in a setting like this is a rare find, and the ability to enjoy this spectacular quality of life within steps to farmers market, gourmet food shops and restaurants, stores, train and everything you need is a dream come true.

$1,250,000 Pending

65 Douglas Road Chappaqua, New York

3 Beds 2 Baths 1,702 SqFt 0.52 Acres

Classic 1920 Colonial brimming with vintage charm and modern updates, ideally located on a desirable cul-de-sac just a short walk to town. This beautifully maintained 4/5-bedroom home features 2 renovated full baths plus a new powder room, a sparkling white renovated kitchen with floor to ceiling cabinetry, stainless steel appliances-Sub Zero, Miele, & Viking and a generous eat-in area with door to an expansive slate patio. renovated baths throughout. Gleaming hardwood floors, graceful architectural details, a cozy fireplace add timeless appeal. The light-filled formal living room and dining room offer gleaming oak hardwood floors, crown molding and many windows. The adjacent family room or home office has windows on three exposures. The second floor features a primary suite with renovated full bath and walk-in closet plus two additional bedrooms and a renovated hall bath. The third floor offers a large bedroom, and an additional playroom/guest/office, and oak floors throughout. Set on nearly an acre (.89) of landscaped grounds with a turfed play area and flat yard, this home offers comfort and convenience inside and out. New Marvin windows, updated mechanicals, gas heat, sewer, and 3-zone heating with central air ensure year-round efficiency. Ample storage in both basement and attic, plus excellent curb appeal, a freshly painted interior & exterior, low taxes, and a prime walk-to-town location make this property an exceptional find.

$1,249,000 Pending

14 Aldridge Road Chappaqua, New York

4 Beds 3 Baths 2,478 SqFt 0.89 Acres

Location, location, location! Traditional 3-bedroom, 2.1-bath colonial-style home serenely set on a prime, flat 1.14-acre parcel. Covered front portico. Spacious living room with wood burning fireplace and hardwood flooring. Formal dining room with bay window, hardwood flooring and door to sunroom (additional 150sqft not included in total) with garden sink and slider to deck with steps to backyard. Eat-in kitchen with picture window to backyard and GE appliances including 4-burner electric cooktop, double in-wall ovens, refrigerator/freezer and dishwasher. Private home office. Rear entryway with powder room and main-level garage access. Rear-corner primary bedroom with two closets and private ensuite bath. Front-corner bedroom and front-facing bedroom with closet access to walk-up, unfinished attic share hall bath with shower over bathtub. Walk-out basement offers recreation room with wood-burning fireplace (additional 400+/-sqft not included in total), large unfinished storage or workshop and utility/laundry room with Whirlpool washer, Maytag dryer, slop sink and door to side yard. New indoor above-ground oil tank. Flat, easy driveway. Rare, flat-as-a-pancake backyard surrounded with lush and mature landscaping. One of the most sought-after neighborhoods in Chappaqua within walking distance to school and close proximity to shops, town and train. A prime opportunity.

$1,200,000 Pending

100 Devoe Road Chappaqua, New York

3 Beds 3 Baths 2,010 SqFt 1.141 Acres

"VICTORIAN SPLENDOR" - A unique opportunity to own an early Grand Victorian home on park-like property with 3 fireplaces, a pool and a barn.Designated a New Castle George Carpenter Historic Landmark dating back to 1780. As you enter the main entrance a flood of natural light welcome you. The two-story projection of the façade’s central section, rising to a peak at the roofline, along with the hand-carved wooden banister, creates a beautifully dramatic entrance. The home possesses a special character of historic and aesthetic interest and value as part of the cultural and social history of the town.Among the most prominent features are the curved corbels or brackets under the eaves, seamlessly blending the character of its 1780 origins.Extra-tall Victorian windows still contain the original hand-blown glass, distinguished by a rippled effect in the living room, parlor and dining room adding a beautiful charm, character and workmanship that can no longer be replicated. The second floor has breathtaking library with at least 12 feet high ceilings, custom built-in bookshelves, 3 bedrooms, 2 baths and an office. Set on an acre level lot, the rear terrace overlooks a garden and pool. Do not miss this special offering.

$1,200,000 Pending

335 Roaring Brook Road Chappaqua, New York

3 Beds 3 Baths 3,112 SqFt 0.99 Acres

Move right into this sparkling, beautifully updated 4-bedroom Colonial, ideally located in the highly sought-after Chappaqua School District. Blending timeless pre-war charm with modern amenities, this home offers exceptional comfort and style.Freshly painted inside and out, the home features beautiful hardwood floors, recessed lighting, a renovated kitchen, updated bathrooms, a wood burning stove and more . A walk-up attic provides excellent storage or future expansion possibilities.Outside, enjoy a large, private property with mature landscaping and perennial gardens, a usable yard, and an expanded driveway accented by elegant Belgian block edging. Additional highlights include an above-ground oil tank and a convenient location close to schools, shopping, dining, transportation, and all that the area has to offer.A truly turnkey opportunity combining character, updates, and convenience.

$1,199,000 Pending

21 Campfire Road Chappaqua, New York

4 Beds 3 Baths 2,207 SqFt 0.38 Acres

Escape to your own private retreat on 3.44 acres of wooded land, where rustic charm meets modern comfort. This unique residence was thoughtfully expanded in 2005 and refined with modern luxuries while preserving its timeless character. The beautifully crafted, freshly painted 2,708-square-foot home offers 3 bedrooms and 4 bathrooms in a serene, nature-filled setting.Inside, you'll find a thoughtfully designed open-concept layout featuring a modern kitchen that flows seamlessly into a stunning log cabin-style living room. In addition, a sun-filled family room provides exceptional flexibility and can easily serve as a fourth bedroom, home office, or guest suite. The first-floor bedroom adds convenience and accessibility for family members and visitors alike.Step outside and discover an extraordinary outdoor lifestyle. Explore your own private forest hiking trails and designated picnic area, enjoy the playground, relax on the inviting front porch, or entertain guests on the expansive stone patio. The property also features a stone-rimmed natural pool, a charming gazebo, and a unique stone pizza oven—perfect for outdoor gatherings, dining, and creating lasting memories.Offering the rare combination of privacy and convenience, this peaceful sanctuary is just minutes from shopping, restaurants, and schools. Located only 35 miles from New York City, it provides the perfect balance of tranquil country living and easy access to world-class amenities.Whether you're searching for a forever home, a weekend getaway, or a vacation retreat, this one-of-a-kind property offers an exceptional lifestyle in a truly picturesque setting.

$1,199,000 Pending

25 Cabin Ridge Road Chappaqua, New York

3 Beds 4 Baths 2,708 SqFt 3.44 Acres

Nestled privately back from the street, this stunning residence offers a seamless blend of indoor elegance and outdoor serenity. The heart of the home is an airy, open-concept first floor anchored by a cozy wood-burning fireplace and a renovated chef’s kitchen. This level flows naturally into a bright family room with exposures on three sides. This level also opens through sliders to an expansive entertaining deck. For quieter moments, a secluded bluestone side patio provides a peaceful escape. The unique side split-level design is tailored for modern lifestyles. Just a half-flight up, you’ll find a restful primary suite and a second bedroom. One more short set of stairs leads to a massive third bedroom with a private bath—a versatile "mega-suite" that easily doubles as a quiet professional workspace or guest wing. Completing the home is a finished walk-out lower level, offering the perfect flexible space for a home gym, media room, or play area, with direct access to the two-car garage. With its blend of private outdoor extensions and dedicated living areas, this home perfectly adapts to your every need. Did we mention the automatic generator? Welcome home!

$1,195,000 Pending

86 Seven Bridges Road Chappaqua, New York

3 Beds 3 Baths 2,407 SqFt 1 Acres

Welcome to 26 Meadow Lane, a pristine 2,178-square-foot ranch set on over half an acre of flat, beautifully landscaped property in one of Chappaqua’s most coveted residential neighborhoods. A rocking chair front porch and Belgian block-lined driveway offer an immediate sense of arrival, while sidewalk-lined streets connect the neighborhood to the acclaimed village of Chappaqua, minutes from restaurants, shopping, playgrounds, the library, Metro-North rail service, and more. Situated within the highly sought-after Chappaqua Central School District, including Roaring Brook Elementary and Robert E. Bell Middle School. The sun-drenched main level features a cathedral-ceiling living room anchored by a dramatic stone fireplace that adds immediate texture, warmth, and luxury to the space. The formal dining room overlooks a stunning yard, while the expansive skylit eat-in kitchen with cathedral ceiling offers an abundance of counter space, a center island, and a built-in entertaining hutch with glass-front cabinetry. A screened porch flows to an expanded stone patio below that lives like a true outdoor living room, seamlessly extending your entertaining space into the beautifully level yard. The primary suite with renovated en-suite bath, two additional bedrooms, a full hall bathroom, and a home office complete the main level. The lower level is anchored by an expansive family room with slider to the patio, complemented by a mudroom, laundry room, half bath, and generous storage throughout. Additional highlights include wood floors, custom closet organizers, extensive crown molding throughout, whole-house generator hookup, dual-zone heating and central air, two-car attached garage, and fresh paint throughout. Legal three-bedroom with flexible four-bedroom living, 2.5 baths, septic, public water, and natural gas. Immaculate, versatile, and perfectly positioned for future expansion.

$1,195,000 Pending

26 Meadow Lane Chappaqua, New York

3 Beds 3 Baths 2,178 SqFt 0.56 Acres

Some homes have good bones. This one has great ones in a private setting. Nestled in Chappaqua's beloved Seven Bridges neighborhood, this 1934 Colonial sits on nearly three-quarters of an acre where tree-lined streets and a true sense of community appeal to buyers who embrace Chappaqua and remain for years. Original hardwood floors, a wood-burning fireplace, crown molding, and a screened porch speak to craftsmanship that simply cannot be replicated. An updated kitchen with granite countertops, wood cabinetry, and a gas range bring real functionality to the floor plan. Main floor offers living room with attached screened in porch, formal dining room, family room / breakfast room, kitchen, huge en-suite bedroom and laundry room. Upstairs holds four more bedrooms, primary ensuite and another full bathroom. Basement has slop sink with laundry hook up and mechanicals. A 2-car garage with a huge walk-up attic, and two additional attics accessed from inside the home give you the space and storage to match your needs. Bring your vision and make it yours in one of Westchester's most sought-after school districts.

$1,100,000 Active

2 Turner Drive Chappaqua, New York

5 Beds 3 Baths 2,715 SqFt 0.73 Acres

Some homes offer space. Others offer a feeling.Tucked along a picturesque tree lined street in the sought after Dodge Farm section of Chappaqua, 28 Valley View Road is a place where privacy, comfort and timeless charm come together beautifully.Privately sited on approximately 1.2 acres, framed by beautiful landscaping, mature plantings and striking stone walls, this thoughtfully designed 3 bedroom, 2 bath home offers a wonderful layout designed for everyday living and effortless entertaining.Step inside to a warm and inviting living room anchored by a wood burning fireplace, flowing seamlessly into the dining area to create comfortable gathering spaces filled with natural light and connection.One of the home's standout features is the expansive screened porch offering nearly 300 square feet of additional enjoyment, creating a seamless extension of the interior living experience. Rainy evening dinners, game nights with friends, quiet mornings with coffee or simply unwinding with a good book become moments to savor while surrounded by peaceful outdoor views. Designed for enjoyment through multiple seasons, this exceptional space brings the beauty of the outdoors closer to home.The kitchen offers timeless appeal with freshly painted solid wood cabinetry, granite countertops and a comfortable eat in area overlooking the backyard. Just outside, a private deck creates the perfect setting to enjoy morning coffee surrounded by mature landscaping and serene property views.The primary bedroom offers an ensuite bath and walk in closet, while two additional bedrooms provide flexibility for a variety of lifestyle needs.The finished walk out lower level adds over 400 square feet of versatile space featuring remarkable wide plank pine flooring reminiscent of craftsmanship rarely found today. Rich in character and warmth, the space lends itself beautifully to recreation, hobbies, workspace, fitness or gathering areas.An oversized attached two car garage offers excellent storage, while the walk up attic presents exciting possibilities for future expansion potential, offering flexibility for evolving needs.Located in the desirable Dogwood Farm area of Chappaqua, known for its peaceful setting while offering convenient access to local shopping, dining, parks, recreation and transportation options, this home presents a wonderful opportunity to enjoy space, privacy and timeless appeal in one of Northern Westchester's most sought after communities.A home designed not simply for living, but for enjoying life's quieter moments beautifully.

$1,099,000 Pending

28 Valley View Road Chappaqua, New York

3 Beds 2 Baths 1,999 SqFt 1.2 Acres

NOW Easy to Show Welcome to this beautifully maintained raised ranch offering the perfect blend of space, comfort, and convenience in a highly desirable Chappaqua P.O. location within the award-winning Pleasantville School District. Situated on a quiet cul-de-sac, this 4-bedroom, 2-bath home features soaring cathedral ceilings, rich red oak hardwood floors, and an inviting open layout designed for both everyday living and entertaining.The spacious living room provides the ideal setting for gatherings and holidays, while multiple freshly stained multi-level decks create seamless indoor-outdoor living perfect for entertaining, summer barbecues, or relaxing evenings overlooking the expansive park-like property. The large yard offers endless possibilities for play, gardening, and recreation, plus three storage sheds for added convenience. Also included is a 11'x54' triangular shaped lot on north side of primary lot. .46 Acre TotalRecent updates including a newer roof and boiler provide peace of mind, while the attached garage adds practicality and storage. Commuters will love the easy 5-minute walk to the Chappaqua train station with approximately 45-minute access to Grand Central Terminal. Rarely offered, this home also includes FREE school bus pickup within Pleasantville’s walking district.Ideally located just minutes from the farmers market, shops, restaurants, parks, and Metro-North, this move-in ready home delivers comfort, charm, and an exceptional lifestyle in one of Westchester’s most sought-after communities. Easy to show same day showings are ok now.

$895,000 Active

249 Mill River Road Chappaqua, New York

4 Beds 2 Baths 2,100 SqFt 0.45 Acres

Welcome to Old Farm Lake - one of Chappaqua's most desirable condominium communities, offering low-maintenance living with resort-style amenities. This 3-bedroom, 2.5-bath townhome is set in a private setting and lives beautifully with natural light across three levels. The main level features an open living and dining area with cathedral ceilings, a skylight, and a wood-burning fireplace. The eat-in kitchen offers granite countertops, custom Rutt cherry cabinetry, stainless steel appliances, and a Sub-Zero refrigerator with direct access to a private patio overlooking the woods. Hardwood floors, a half bath, and one-car garage access complete the main level. Upstairs, the primary suite includes an en-suite bath and walk-in closet, with two additional bedrooms and a full hall bath. The lower level offers finished storage or a dedicated workspace. Community amenities include a pool, tennis courts, sport court, fitness center, clubhouse, and playground - all maintained for you. Just 1 mile to the Chappaqua train station and village.

$890,000 Active

20 Waters Edge Chappaqua, New York

3 Beds 3 Baths 1,569 SqFt 0.01 Acres

Welcome to Apple Hill Farm, sitting on highly desirable, 37+ Wooded Acres. Where calm meets comfort. This corner Townhome, located in a cul-de-sac for added privacy, features a manicured lawn and a carefully curated garden. Experience modern elegance in this home, with high ceilings, lots of Windows and Skylights that bring abundant natural daylight and sunlight indoors. It has 3 Bedrooms and 2.5 Bathrooms, many updates throughout the home, including the exterior deck. The Living Room has custom built-ins. An inviting Dining Room for memorable meals and an Eat-in-Kitchen with quartz countertops and stainless steel appliances, both rooms have sliding doors onto the deck. It features hardwood floors throughout, many closets and storage spaces. The Primary Bedroom has a Juliet Balcony, En-Suite bathroom with Double sink vanity, Second Bedroom with Skylights, Third Bedroom with Hallway Bathroom. Close to Train, Close to Downtown Dining and Shops, Close to Schools. Property includes 1-Car Attached Garage with Driveway for 1 additional car. Amenities include: Inground Pool and Tennis Courts.

$879,000 Active

2 Timberland Pass Chappaqua, New York

3 Beds 3 Baths 1,586 SqFt 0.56 Acres

$809,000 Active

73 S Bedford Road Chappaqua, New York

4 Beds 3 Baths 1,584 SqFt 0.26 Acres

TURNKEY in every way! Beautiful End Unit Townhouse in Old Farm Lake with private wooded views. Spacious Living Room with Wood Burning Fireplace and Cathedral Ceilings. Open Floor Plan with Living Room/Dining Room combination and sliding glass doors out to Deck. Renovated Eat in Kitchen with Carrera Marble counters and Stainless Steel Appliances -- including Bosch Dishwasher, Fisher & Paykel Refrigerator, GE Gas Range and Oven. Entry Foyer with Coat Closet, Powder Room & Door to Garage. Second Floor includes a spacious Primary Bedroom Suite with Walk-in Closet & Updated Primary Bathroom. An Additional Bedroom Ensuite with Full Bath, Laundry Area with New GE Washer/Dryer and Pull Down Stairs to Attic. Complex has Pool, Tennis, Clubhouse, Paddle/Basketball Court and Playground. Convenient to Chappaqua Schools, Library, Shopping, Train Station, Parks & Recreation. Easy NYC Commute. THIS HOME IS NOT TO BE MISSED!

$799,000 Pending

127 Stone Bridge Square Chappaqua, New York

2 Beds 3 Baths 1,244 SqFt 0.001 Acres

Straight from the pages of a storybook, this enchanting French Revival Tudor-inspired home is tucked amongst a canopy of mature trees and natural stone walls which create an unforgettable first impression. A winding stone walkway leads to a charming covered entry highlighted by a stained glass front door, hinting at the warmth and character that await inside. Living room with fireplace, eat-in kitchen with farm sink, beamed ceilings, and updated appliances with access out to a large terraced patio. Offering three Bedrooms, the primary bedroom/bath provide access to third floor flexible space as office/studio with additional storage. Finished lower level designed for versatility as recreation/media/playroom, complete with powder room, laundry, utilities and garage. Rich in architectural detail and overflowing with charm, this is the kind of home that instantly captures your heart. Award winning Chappaqua school district; 4 minutes to the Chappaqua metro north train station, 46 Min. express to Grand Central, 0.9 miles to town.

$790,000 Active

220 Mill River Road Chappaqua, New York

3 Beds 2 Baths 1,538 SqFt 0.515 Acres

Offering over 1650SF of living space, this spacious townhouse in the sought-after Old Farm Lake community has private wooded views and an open, light-filled floor plan. The living room which is open to the dining area, features cathedral ceilings, a wood-burning fireplace, and sliding glass doors to a private deck. A renovated eat-in kitchen is well- appointed with granite countertops and stainless-steel appliances. Additional on this level is a den/office and powder room. The second floor offers a spacious primary suite with cathedral ceiling, a custom organized walk-in closet and ensuite bathroom. The second bedroom also has an ensuite bathroom. Basement provides a great place for all of your storage. Enjoy resort-style amenities including a pool, tennis courts, clubhouse, paddle and basketball courts, and playground. Conveniently located in the Chappaqua School District, just minutes from shopping, parks, Metro-North, and an easy commute to New York City.

$750,000 Pending

110 Woods End Road Chappaqua, New York

2 Beds 3 Baths 1,653 SqFt 0.01 Acres

Welcome to 134 Bayberry Close in the sought-after Old Farm Lake community, in the heart of Chappaqua. This spacious 2-bedroom, 2.5-bathroom townhouse offers over 1,800 sq ft of living space across three levels, including a finished walk-out lower level. The main level features an eat-in kitchen, a dining area with sliding glass doors to the deck, and a sun-filled living room with cathedral ceilings and a fireplace. Upstairs, the nicely sized primary suite offers a walk-in closet and en-suite bath, while the second bedroom features its own full bath. Laundry is conveniently located on the upper level. The lower level provides valuable flexible living space, featuring a family room and a separate area ideal for a home office, gym, or guest space. Residents enjoy exceptional community amenities including pool, tennis courts, clubhouse, playground, and basketball court, all just minutes to town, train, shopping, and top-rated Chappaqua schools. A rare opportunity to own in one of Chappaqua’s most desirable condominium communities. Additional highlights include a new water heater, central air, natural gas heat, attached 1-car garage, and excellent storage.

$725,000 Pending

134 Bayberry Close Chappaqua, New York

2 Beds 3 Baths 1,818 SqFt 0.01 Acres

Experience the best of convenient living in this stylishly updated 3-bedroom home, perfectly situated in a walk-to-all neighborhood near the train, schools, shopping, and library. This meticulously maintained property boasts significant modern upgrades, including double pane windows, Hardiplank siding, and a spacious Trex deck overlooking a private, flat, grassy backyard. Inside, enjoy hardwood floors and LED lighting throughout, leading you into a bright living room with crown molding and large windows that frame the deep front yard. The kitchen is a chef's delight, featuring quartz countertops, a deep stainless steel sink, and stainless steel appliances, including a gas range and French door refrigerator. The king-size primary bedroom has an en suite bathroom and offers direct access to the deck, while the walk-out lower level adds versatile living space, complete with a private office, a third bedroom with an en-suite bath, and laundry. This home is ready for you to move in and enjoy!

$685,000 Pending

80 Bischoff Avenue Chappaqua, New York

3 Beds 3 Baths 1,299 SqFt 0.19 Acres

Welcome to Chestnut Oaks. Corner unit Townhome located in building 5 featuring 2 bedrooms, 2 full baths, fireplace, attached garage and balcony. Located in the heart of Chappaqua and close to train, town and schools. Renovated in 2010 with new dine-in kitchen, granite counter tops, stainless steel appliances, hardwood floors, renovated primary bathroom, custom walk-in closet, new washer/dryer and Bose speakers. Community outdoor pool and tennis.

$649,000 Active

353 N Greeley Avenue 353 Chappaqua, New York

2 Beds 2 Baths 1,458 SqFt 0.001 Acres

Welcome to 309 N. Greeley Avenue. This lovely first floor Town House in the sought-after Chestnut Oaks Community is conveniently located to the heart of downtown Chappaqua. With the award-winning Chappaqua School District and proximity to a Metro North station, this property will not last! This Two Bed, 1 Bath unit has a great layout with a front and back patio! There are no stairs (just one step-down to a sunken Living Room)....enter into this unit and all rooms are one the same level! The main living room is both open and airy with a high ceiling, fireplace and two sliding glass doors leading out to lovely patios and open space. The complex features a swimming pool, tennis and a garden. Make your appointment today!

$579,000 Active

309 N Greeley Avenue 5C Chappaqua, New York

2 Beds 1 Baths 1,200 SqFt 10.063 Acres

Opportunities like this do not come around often in Chappaqua, and when they do, they tend to move quickly. What is being offered at 58 Maple Ave is a flat, level, in-town parcel with an existing 2-bedroom, 1-bath cottage set back from the road among towering pines, in one of Westchester County's most coveted villages. Whether a buyer chooses to develop the land, renovate what is there, or simply occupy the existing structure while planning next steps, the opportunity here is defined first and foremost by the location and the lot.The cottage itself, built in 1930 and totaling 711 square feet, is being sold strictly as-is. It sits on a 0.28-acre lot with driveway parking and includes a front deck, a patio, and a yard with a quiet, private feel that genuinely surprises you given how close you are to the center of town. Inside, the main level includes a great room with cathedral ceilings and built-in features, a kitchen, two bedrooms, and a full bath. A partial basement with Bilco door access houses laundry and mechanicals. The structure has a history as a consistently rentable asset in a market where rental demand is strong and vacancy is rare, which speaks to the enduring appeal of this particular address regardless of what a future owner ultimately decides to do with it.The location is the defining feature and the reason this property commands the attention it does. You are minutes on foot from the Chappaqua Metro-North Station, putting Midtown Manhattan within comfortable commuting distance without the stress of a car or a parking lot. The village's boutique shops, restaurants, and parks are equally walkable, giving this address an everyday livability that most Westchester properties simply cannot replicate. For those who travel frequently for business, Westchester County Airport is also easily accessible. This is a genuinely rare convergence of walkability, transit access, and village character that defines the upper end of what Chappaqua real estate has to offer.The property falls within the Chappaqua Central School District, one of the most highly regarded public school systems in New York State and a consistent driver of demand in this market.Flat lot, set-back privacy, walk-to-train location, and Chappaqua schools.

$549,000 Active

58 Maple Avenue Chappaqua, New York

2 Beds 1 Baths 711 SqFt 0.28 Acres

Welcome to Chestnut Oaks, a sought-after condominium community just moments from downtown Chappaqua. This sun-filled 1-bedroom plus loft and den residence offers 5 well-designed rooms, 1.1 updated baths, and a flexible layout ideal for today’s living. The inviting entry hall features tile flooring and a generous closet, leading to an updated powder room accented by a charming octagonal window and Carrera marble floor. The renovated kitchen showcases stainless steel appliances, crisp white cabinetry, black granite countertops, and a Carrera marble subway tile backsplash, with a convenient pass-through to the dining area. The expansive living/dining room is highlighted by laminate wood flooring, recessed lighting, oversized windows, and a dramatic partial cathedral ceiling—perfect for entertaining or relaxing. Upstairs, the spacious primary bedroom includes wall-to-wall carpeting, recessed lighting, crown molding, and two double closets. An updated dual entry bath, from the hallway and primary bedroom, features gray tile flooring and a white tile tub surround. The open loft, with sliding glass doors to a private balcony, provides an ideal home office or reading nook. Additional features include a versatile den or guest space with crown molding and clerestory windows, and a convenient laundry closet with stackable washer and dryer. Enjoy complex amenities including an outdoor pool and tennis court. Ideally located close to shops, restaurants, library, park, farmer’s market, and train to NYC, this residence offers comfort, convenience, and a true Chappaqua lifestyle.

$510,000 Pending

368 N Greeley Avenue Chappaqua, New York

1 Beds 2 Baths 1,207 SqFt 0.001 Acres

$499,999 Active

150 Bedford Road 12A Chappaqua, New York

2 Beds 2 Baths 924 SqFt 0.001 Acres

Chappaqua, N.Y.

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