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:

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.

$3,677,000 Active

20 Bessel Lane Chappaqua, New York

6 Beds 6 Baths 8,200 SqFt 4.11 Acres

Nestled on over 5 private, professionally landscaped acres in the exclusive cul-de-sac of Sutton Farm within Chappaqua’s esteemed Whippoorwill area, this custom-designed and custom-built Shingle Style home is a rare and refined first opportunity. Completed in 2008 by a renowned builder and architect, the 4+ bedroom home (lives like a 5/6) has been meticulously detailed with luxurious, high-end finishes that elevate every detail. A gracious covered front entry welcomes you to a dramatic two-story foyer with soaring ceilings, a sweeping curved staircase, and exquisite architectural detailing throughout. The shingle and stone facade exudes timeless curb appeal, while inside, craftsmanship and quality reign supreme. The thoughtfully designed open layout showcases wide-plank white oak floors and designer light fixtures from Holly Hunt, Visual Comfort, Jonathan Adler, and Boyd, imbuing each space with modern sophistication. At the heart of the home is a professionally appointed chef’s kitchen. A dual oven 6-burner range with grill by Wolf is accented by a custom-designed stainless steel hood. Built-in Subzero refrigeration features dual 36’ refrigerator freezers. Quartz and marble countertops, two dishwashers, and two sinks complete this exquisite space. Ideal for both entertaining and everyday living, the inviting breakfast area flows seamlessly into the sun-drenched family room with a custom masonry stone fireplace. The main level also includes a formal dining room with butler’s pantry, a gracious living room with a second masonry fireplace, a sunlit private office, and a well-equipped mudroom with back staircase. The second level includes a separate guest suite/bonus room and additional office space—ideal for multigenerational living or working from home. The luxurious primary suite offers a peaceful retreat with a tray ceiling, a dressing area, generous walk-in closets, and a spa-like bath. Three additional spacious bedrooms each feature en-suite baths. The finished walk-out lower level adds remarkable versatility with a large recreation room, game room, gym, full bath, guest/office suite, and abundant storage.The exterior grounds are truly an outdoor oasis: sweeping lawns, specimen trees, perennial gardens, and complete privacy. A newly paved Belgian block-lined driveway provides a grand entrance, while the expansive backyard features an oversized deck, perfect for entertaining, recreation, or serene relaxation. Additional highlights include a three-car, double-height garage, radiant heat, and whole-house generator—offering ultimate comfort, efficiency, and peace of mind. Located on once historic Sutton Farm, this one-of-a-kind home offers the best of both worlds: seclusion and serenity just minutes from Chappaqua, Armonk, schools, and train. Nature preserves are nearby for peaceful hikes. A rare and refined opportunity—perfection in every detail.

$3,499,000 Active

5 Sutton Farm Drive Chappaqua, New York

4 Beds 7 Baths 7,708 SqFt 5.05 Acres

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

$3,199,000 Pending

93 Haights Cross Road Chappaqua, New York

4 Beds 5 Baths 6,542 SqFt 3.66 Acres

Welcome to 70 Haights Cross, an architectural masterpiece in one of Chappaqua’s most coveted neighborhoods. Designed by acclaimed architect Tasos Kokoris, this turn-key 5-bedroom, 7.2-bath colonial blends timeless elegance with today’s most sought-after amenities. Nestled on over two acres of private, professionally landscaped grounds, the property showcases a resort-like setting with a Gunite pool, waterfall, and jacuzzi. Perfect for both everyday enjoyment and entertaining. Inside, the heart of the home is the sun-drenched gourmet kitchen, thoughtfully outfitted with a Wolf 6-burner range, warming and fridge drawers, dual Bosch dishwashers, and a Subzero refrigerator. An expansive family room with a gas fireplace, a rich wood-paneled library with wood-burning stove, a sophisticated home office, and an upstairs gathering room create spaces designed for comfort and connection. The lower level elevates the lifestyle experience with a dramatic garden room opening to a stone patio, two full baths, a recreation room, lounge, sitting area, and mudroom. Bordering the scenic Glazier Arboretum and its tranquil hiking trails, this home offers the perfect balance of luxury and nature. Located within the highly sought-after Chappaqua School District, 70 Haights Cross is more than a residence, it’s a lifestyle. Experience the pinnacle of Westchester living in a private and serene retreat, just minutes to Chappaqua village, train, and parkways.

$3,150,000 Active

70 Haights Cross Road Chappaqua, New York

5 Beds 9 Baths 8,775 SqFt 2.17 Acres

Rare opportunity to move right into one of the most beautiful homes in the area! This fully renovated 5BR, 4 full & 2 half bath Colonial sits on 2.46 private acres at the end of a cul-de-sac in one of Chappaqua’s most coveted neighborhoods. Blending timeless charm with modern updates, the home features a chef’s kitchen with high-end appliances, sun-filled living spaces, custom millwork, and an ideal layout for everyday living and entertaining. The spacious primary suite is complemented by four additional well-sized bedrooms. Outside, enjoy resort-style living with a heated gunite pool, bluestone patio, lush landscaping, and expansive, fully fenced-in backyard. Conveniently located close to town, award-winning Chappaqua schools, shopping, and train. A turnkey gem in a premier location!

$2,950,000 Pending

3 Round Hill Place Chappaqua, New York

5 Beds 6 Baths 5,285 SqFt 2.46 Acres

Exciting and new state-of-the-art expansion and renovation by highly recognized local developer, Tavo Development teaming with noted architect Teo Seguenza. Ready for occupancy in Spring 2026. Meticulous attention to detail, years of experience and master craftsmanship are combined in this new offering, encompassing 5,536 sq ft, 4 bedrooms, 5 full and 2 half baths, a finished walk-out lower level and all the modern amenities for today’s discerning buyer. The light-filled main level highlights a chef’s kitchen with island and breakfast room, formal living room and dining room, family room, large mudroom and a screened in porch. Upstairs, the primary suite is enhanced with a spa-like bath and oversized walk-in closet. Two additional ensuite bedrooms, bonus room with access to a large balcony and laundry complete the upper level. The lower-level with an exercise room, lounge, laundry and full bath segues to the outdoors with almost an acre of flat usable grounds and site plan approval for a pool. Interior pictures displayed are samples of previous Tavo built homes.
A perfect combination of style, space, and comfort. Close to town, highways and 50 minutes to NYC.

$2,850,000 Active

211 Bedford Road Chappaqua, New York

4 Beds 7 Baths 5,536 SqFt 0.95 Acres

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

$2,699,000 Pending

35 Overlook Drive Chappaqua, New York

4 Beds 7 Baths 5,354 SqFt 1.22 Acres

Meticulously maintained, beautifully appointed 4-bedroom, 4 full and 1 half-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 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 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 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. 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.

$2,575,000 Active

17 Byram Meadows Road Chappaqua, New York

4 Beds 5 Baths 6,640 SqFt 1.02 Acres

Located in the coveted Whippoorwill estate area, 61 Carolyn Place presides on 2.19 manicured acres and overlooks the Whippoorwill Country Club’s private golf course. Meticulous details abound with lofty ceilings and spacious rooms, complemented by warm, inviting, intimate spaces and outdoor areas. An open gourmet kitchen and breakfast room flow to the grand two-story family room and dedicated solarium, both accessing a large outdoor deck and rocking chair porch. The second-floor features a large primary suite with a gorgeous, sun-drenched bedroom complete with western-views and a wood burning fire place. A sitting room/second office, double walk-in closets, and a lavish bath with a jacuzzi tub, dual vanities and a spacious shower complete the suite. A wide hallway spanning the breadth of the home gives access to two additional ensuite bedrooms, the upstairs laundry room, and home office. The home’s eastern wing, features the final two bedrooms, connected by a Jack-and-Jill bath and features a Juliet balcony overlooking the front yard. A heated, three car garage, connecting mudroom, and full, walk-out basement complete the interior, while the expansive front and backyards feature vast rolling lawns, beautiful scenery, and a potential pool site. The home's assessment has been grieved to correlate to the original list price of $2.8M and will take effect in April 2026. This will substantially lower the property taxes with opportunities to further reduce the assessment in June of 2026. The home is conveniently located between Chappaqua and Armonk, close to town and highways, and approximately 50 minutes to NYC, 61 Carolyn Place is a truly remarkable home and not to be missed.

$2,500,000 Pending

61 Carolyn Place Chappaqua, New York

5 Beds 6 Baths 5,907 SqFt 2.19 Acres

Timeless elegance meets modern comfort in this enchanting 1901 hunting lodge, masterfully restored in 1991 and recently enhanced. Set on beautifully landscaped grounds with lush gardens, this distinguished home features a dramatic front portico, high ceilings, intricate millwork, and unique architectural details throughout. Grand living spaces include a library/home office with French doors and fireplace, a formal living room with built-ins, fireplace, and terrace access, and a dining room with fireplace that opens to a sun-drenched three-season room. The custom chef’s kitchen features a center island, marble countertops, high-end appliances, and an adjoining octagonal breakfast room with cathedral ceiling and clerestory windows. A family room and mudroom/laundry with garage and yard access complete the main level. Upstairs, the spacious primary suite offers a walk-in dressing room and spa-like bath. Additional bedrooms include one with ensuite bath and walk-in closet, one with a fireplace, and one with built-ins. The finished third floor offers a bedroom, full bath, and flexible bonus room. Additional highlights include updated mechanicals, a 17kW whole-house generator, a detached garage, and numerous enhancements made over the past few years. A rare opportunity to own a truly special home filled with character, comfort, and timeless style in a prime location.

$2,200,000 Pending

77 Haights Cross Road Chappaqua, New York

5 Beds 5 Baths 4,172 SqFt 2.6 Acres

50 Overlook Drive, an elegant 6-bedroom colonial Tudor set in a quiet, tree-lined neighborhood. With fresh upgrades completed this month, including interior repainting, carpet-removal to expose wood floors. This one-of-a-kind home is a must see.
Meticulously maintained heating and cooling systems, brick exterior, and a classic-tile roof are some of the exceptional features this home can offer. Homes built to this quality are a rare find. Constructed in 1929, the home is also graced with soaring ceilings, intricate period moldings, and expansive sunlit interiors.
Designed for both grand entertaining and comfortable living, this spacious home is roaring with charm and can suit a variety of tastes and living styles. The first floor offers a living room with fireplace, an all seasons sunroom, a bright and airy dining room, a kitchen with pantry and wet-bar, a half bath, and an in-law or au pair suite with a full bath. Upstairs features 5 bedrooms and 3 full baths, a grand hallway, and attic access. Additional recreational space is provided in the finished basement, with a family room, a gym, and large mudroom, a half-bath, and a utility room.
The beautifully landscaped 1.2-acre lot boasts stunning specimen plantings and a private stone patio adjacent to the all-seasons sunroom. There is also a charming bridge, designed by renowned architect Ned Baldwin, leading to a park-like setting in the backyard.
This is an incredible opportunity to own a truly distinguished home in one of Chappaqua’s most desirable neighborhoods. Experience the perfect balance of classic architecture and modern luxury in this extraordinary residence, in a home that is built to stand the test of time.

$2,000,000 Pending

50 Overlook Drive Chappaqua, New York

6 Beds 6 Baths 5,234 SqFt 1.2 Acres

Stunning and elegant 5 bedroom/5.5 baths ranch style home plus detached garage studio with full bath and kitchenette. Luxuriously appointed. Custom millwork featured in every room. Open floor plan, living room with marble floors, fireplace surrounded by built-in shelving with adjacent dining room with built-in cabinetry and buffet. Custom kitchen with oversized marble island, custom cabinetry and new appliances. Large eat-in area. Separate pantry /mudroom with abundant storage. Library with pocket french doors, and built-in book cases. Primary suite with a wall of custom cabinetry, walk-in closet, marble bath plus private balcony. Each bedroom features custom built-ins. Two additional ensuite bedrooms. Large family room with entertainment center and full bath. Sought after detached garage with beautifully appointed studio featuring large work area, kitchenette and a full bath with storage and built in cabinetry. Centrally located in Chappaqua, close to the train and all highways.

$1,850,000 Coming Soon

675 Quaker Road Chappaqua, New York

5 Beds 6 Baths 4,616 SqFt 1.04 Acres

Move-in ready, light and bright 3 bedroom/ 3.5 bathroom home that can live like a 5 bedroom in the coveted Lawrence Farms South neighborhood with a private, flat backyard with a stone patio, heated gunite pool and a charming pergola. This inviting home with high ceilings throughout, offers a spacious living room with a fireplace, adjacent to a formal dining room, both with glass door access to the backyard and pool, plus a chef's kitchen with center island, granite countertops and high-end appliances and glass surrounded breakfast area, also with access to the backyard. There is a very large first floor primary bedroom with 2 walk-in closets and a roomy primary bathroom with double sinks, shower and whirlpool tub. Also on the first floor, there is a half bathroom, an additional bedroom with double closets, plus an office/den with a wet bar and lots of built-in cabinets and shelves, a full bathroom, a laundry area and access to the garage and lower level. On the second floor there is a large bedroom, a full bathroom and another nice-sized room, perfect for a playroom or additional bedroom. This pristine and well-maintained home with lots of special features in one of Chappaqua's prime developments is close to all and an amazing offering; not to be missed!

$1,850,000 Active

24 North Way Chappaqua, New York

3 Beds 4 Baths 3,960 SqFt 1 Acres

Welcome to 56 Annandale Drive, Chappaqua, a capacious and captivating Cape Cod commandingly set on 1.4 acres in sought-after Lawrence Farms East within walking distance to Mount Kisco Country Club, Kittle House, Chappaqua Crossing, Horace Greeley High School and the town of Mount Kisco. Built for entertaining, every day is a holiday to celebrate in the open, spacious interiors, starting with the inviting front-facing living room with wood-burning fireplace. The gourmet kitchen is equipped with solid wood cabinetry with pull-out shelving, tile backsplash, stone countertops, center island with prep sink, 5-burner cooktop, dual Thermador in-wall ovens, GE microwave, Sub-Zero refrigerator/freezer, and a Viking dishwasher. Host feasts or fests in the dramatic formal dining room with wood burning fireplace and opposing sets of French doors to opposing patios. BBQ on the built-in grill and dine alfresco on the patio. The party continues in the extra-spacious family room with large windows on three sides. Main-level private quarters include a front-facing in-law or guest suite with private, ensuite bath; and the king-sized primary suite endowed with its own sitting/dressing area, a sumptuous, private, resort-worthy ensuite bath, and French doors to the patio with swim spa for rejuvenation or relaxation. Completing the main-level are the entry foyer with two separate coat closets, broom closet and powder room; and a front-to-back mud room with front- and rear- facing French doors and garage access. Upstairs houses a wide, front-facing lounge or play space adjoining two rear-facing bedrooms with built-ins, outfitted, dormered closets with attic access, and sharing a “Jack-n-Jill” bath with double vanity, linen closet and tiled shower with in-wall jets and regular and handheld showerheads. Downstairs sit two generously sized recreation rooms; a full bath with shower; a laundry room equipped with Whirlpool front-loading washer and dryer, sink, ironing board and built-in cabinetry; storage; mechanicals; and access to the attached 3-car garage with electric car charger. An alarm system and a standby, backup, whole house generator help protect it all. A sweeping drive provides plenty of off-street parking. Lovely lawns and landscaping add colorful accents, and mature and established trees ring the perimeter of the property. A distinctive residence in a notable location.

$1,799,000 Pending

56 Annandale Drive Chappaqua, New York

4 Beds 5 Baths 4,543 SqFt 1.404 Acres

Welcome to 20 Wallace Way – a rare offering in the sold-out Chappaqua Crossings Carriages community. This sophisticated Byram Wetherby model redefines townhouse living with nearly 3,000 sq. ft. of thoughtfully curated interiors, exceptional finishes, and inviting outdoor spaces. Ideally set along an expansive open lawn, the home enjoys abundant sunlight, privacy, and serene views throughout the day.

The main level is designed for both everyday living and entertaining, featuring a dramatic great room with fireplace and seamless connection to the chef’s kitchen. A striking oversized island anchors the space, complemented by custom cabinetry, premium appliances, and an elegant dining room with adjacent butler’s pantry. A bright home office/library adds versatility, while a stylish mudroom with built-ins leads to the two-car garage with electric charger and ample storage. Upstairs, the primary suite serves as a serene retreat, complete with a spa-inspired bath and a spacious walk-in closet. A well-appointed secondary bedroom and bath offer comfort for family or guests. Enhancing the level even further is an oversized sunlit loft, complete with a wet bar, that flows seamlessly to a private rooftop terrace—an ideal setting for both quiet evenings and lively gatherings.

Life at Chappaqua Crossings Carriages extends well beyond the front door. Residents enjoy walkable access to the pool, clubhouse, and fitness center, as well as nearby Whole Foods, Life Time, shops, and restaurants. A dedicated shuttle to the train offers effortless Manhattan commutes, while golf courses, parks, and the best of the Hudson Valley are just minutes away.
Built by Toll Brothers, celebrated for their quality and craftsmanship, 20 Wallace Way seamlessly blends modern design, luxury amenities, and the charm of a vibrant community.

$1,699,000 Active

20 Wallace Way Chappaqua, New York

2 Beds 3 Baths 2,906 SqFt 0.06 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

Welcome to this sophisticated 4-bedroom, 3.5-bath contemporary residence, perfectly designed for today’s lifestyle with a seamless blend of modern style and functional comfort. Set on a gracious property, this home offers open, luminous living spaces flooded with natural light and thoughtful architectural detail throughout. At the heart of the home, a beautifully appointed kitchen opens to a spacious family room—ideal for relaxed gatherings and everyday living. The formal living room is a true standout, featuring near wall-to-wall windows that frame the surrounding landscape and bathe the room in sunlight. A formal dining room provides a refined setting for entertaining, while the flowing layout ensures effortless movement between spaces. The coveted main-floor primary suite offers privacy and ease, with serene views and a spa-like en-suite bath. Upstairs, three additional bedrooms provide comfort and flexibility for guests, family, or work-from-home needs. Beyond the home’s design, the location truly shines—just minutes from town, Metro-North train service, top-rated local schools, and the convenience of Whole Foods Market. Whether you're commuting, shopping, dining, or enjoying the community, everything you need is close at hand. With expansive windows, sunlit interiors, multiple living and dining areas, and a prime layout designed for both entertaining and retreat, this home offers the best of contemporary living in a timeless and highly convenient setting.

$1,650,000 Pending

6 Whippoorwill Lake Road Chappaqua, New York

4 Beds 4 Baths 3,244 SqFt 1.47 Acres

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

$1,599,995 Pending

15 Wallace Way 20 Chappaqua, New York

3 Beds 4 Baths 3,353 SqFt 0.08 Acres

Timeless elegance meets modern comfort in this beautifully updated Colonial home. Double entry front doors open to a gracious foyer, setting the stage for the home’s expansive and light-filled layout. At its center, the renovated chef’s kitchen impresses with gleaming Caesarstone countertops, professional-grade stainless steel appliances, dual dishwashers, an oversized island with prep sink, ample counter seating, and abundant pantry and cabinet storage. Designed as the true heart of the home, the kitchen flows into a sun-drenched four-season sunroom—an inviting space for casual dining, quiet reading, or relaxed evenings. Off the kitchen is an elegant dining room and spacious living room perfect for grand entertaining and everyday comfort. An elegant powder room and home office add refinement and functionality. Thoughtfully connected to the main living areas, a bedroom with full bath, family room, and sitting room provide flexible space for everyday living, while a separate entrance offers the option of a private guest or in-law suite. Upstairs, the large primary suite is a luxurious sanctuary, featuring an expansive walk-in closet and a spa-like full bathroom with large glass shower. Two additional bedrooms share a well-appointed full bath with bathtub. An upstairs laundry area provides convenience at your fingertips.
The lower level offers exceptional versatility, with generous storage, a secondary laundry room, and access to the oversized garage—large enough to accommodate three vehicles. Two attics provide additional storage solutions.
Outdoors, a spacious deck with an electric awning overlooks the level, fenced-in backyard. The entire house is framed by mature trees, professional landscaping, and vibrant plantings. Additional amenities include a full-house generator, basketball hoop and an enviable location close to schools, train, shops, parks, and with direct access to the North County Trailway.
This turnkey Colonial combines classic sophistication, modern amenities, and a welcoming floor plan—perfectly suited for today’s lifestyle and ready to be cherished by its next owners.

$1,599,000 Pending

35 Whitlaw Lane Chappaqua, New York

4 Beds 4 Baths 3,732 SqFt 1.13 Acres

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

$1,575,000 Pending

58 Spring Lane Chappaqua, New York

4 Beds 3 Baths 3,457 SqFt 2 Acres

Hywood Ledge is a spectacular expanded ranch in the desirable Deepwood neighborhood of Chappaqua, which presents sophisticated charm and tranquility. This cedar-shake beauty is perfectly situated at the end of a cul-de-sac on 1.9 acres, offering unparalleled privacy, yet only 5 minutes to the center of town and the Chappaqua Metro-North. The home was renovated between 2000-22 offering years of peace of mind with quality upgrades: new roof (2020); new boiler (2020); new above-ground oil tank (2020); new 1250 gallon septic tank (2020); new Marvin Elevate, divided light windows (2021); professional landscaping (2021); electrical updates that include a 220V garage car charger and a house generator interlock with electrical sub-panel (2021); Belgium block driveway (2022). A gorgeous great room with James Allan lighting anchors the house with a wood burning fireplace, across from the beautifully renovated eat-in kitchen with custom maple Omega cabinetry. A chef’s dream is complete with large Viatera Quartz countertops plus state-of-the-art Wi-Fi supported Samsung induction cooktop and Family Hub refrigerator. Stunning floor to ceiling wrought-iron doors lead to a new multi-level Trex deck perfect for outdoor entertainment. The home’s wonderfully curated renovations carry through to the first-floor primary bedroom, with an ensuite bath with Italian mosaic tile work surrounding the spa like walk-in shower accompanied by a gorgeous copper soaking tub. The lower-level features two beautiful bedrooms with their own personal full bathroom. The bonus recreation room offers numerous possibilities for additional living and workspace. The moment you drive through the stone entry pillars, you will want to call Hywood Ledge your own.

$1,550,000 Pending

27 Deepwood Hill Chappaqua, New York

3 Beds 3 Baths 2,830 SqFt 1.962 Acres

Welcome to 9 Point Place, an exquisite, 4-bedroom, 3.5-bath Colonial located at the end of a cul-de-sac. This home offers approximately 4,100 sq ft of beautifully finished living space on nearly half an acre in the desirable Chappaqua school district. Step inside to an open, light-filled layout ideal for everyday living and entertaining. The kitchen features high-quality finishes and flows seamlessly to the dining and living areas. Sliders, off of the family room, lead to a spacious outdoor area with its own fireplace and grill making it ideal for relaxing or dining al fresco. This property boasts an expansive, fenced-in backyard perfect for outdoor gatherings or quiet reflection in a peaceful setting. Upstairs, the serene primary bedroom offers a luxurious ensuite bathroom, while three additional bedrooms provide flexible space for family, guests, or a home office. Enjoy the convenience of an attached 2-car garage. Ideally located just minutes to Chappaqua’s charming shops, dining, and train station for an easy NYC commute. Smart Home WIFI electronic system throughout, and a full house generator run by natural gas are just a few of the many features this home has to offer.

$1,550,000 Pending

9 Point Place Chappaqua, New York

4 Beds 4 Baths 4,100 SqFt 0.48 Acres

Welcome to this beautifully maintained home featuring a spacious 476 sq ft sunroom with direct access from both the living room and family room—ideal for year-round enjoyment. Recent updates include a new roof (2023), new central air unit (2022), and all new water and heating systems in the basement, offering peace of mind and modern efficiency. The family room boasts a classic wood-burning fireplace, perfect for cozy evenings. Enjoy a formal dining room and an eat-in kitchen, great for everyday living and entertaining. A generous deck overlooks a large backyard, providing ample space for outdoor relaxation. Conveniently located near Metro-North and the towns of Chappaqua and Armonk, this home blends comfort, convenience, and charm.

$1,500,000 Active

7 Byram Meadows Road Chappaqua, New York

4 Beds 3 Baths 2,891 SqFt 0.92 Acres

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

$1,399,995 Pending

13 Wallace Way 19 Chappaqua, New York

2 Beds 4 Baths 2,945 SqFt

Experience the pinnacle of refined living in this newly reimagined modern farmhouse, perfectly sited on a secluded, tree-lined acre in the heart of Chappaqua. With over 2,800 square feet of exquisitely finished space, this residence blends timeless architectural detail with sophisticated, high-end design for the ultimate in quiet luxury. Andersen 400 series windows and doors throughout, most are six-foot in height, enhance natural light and frame serene woodland views. A dramatic vaulted great room sets the tone with white oak floors, exposed beams, and a wood-burning fireplace, opening to a bespoke chef’s kitchen outfitted with custom shaker cabinetry, granite counters, and a striking oversized island—ideal for elevated entertaining. The floorplan flows effortlessly from an intimate dining area to a cozy mezzanine retreat above. The luxe primary suite is a private sanctuary, featuring a tree-top balcony and a spa-level bath with floating vanities, soaking tub, and walk-in glass shower. The lower level offers a custom-designed entertainment lounge with wet bar and game room, opening to an expansive bluestone patio for seamless indoor-outdoor living. A charming covered front porch, lush lawns, and a tranquil brook complete this idyllic setting. Nestled just moments from Chappaqua Crossing—home to Whole Foods, Lifetime Fitness, dining, shopping, and medical facilities. Metro-North and major parkways are easily accessible for effortless commuting. Located in the nationally recognized Chappaqua School District. Meticulously renovated with every luxury in mind, this designer home delivers a rare blend of comfort, elegance, and convenience in one of Westchester’s most desirable communities.

$1,375,000 Active

136 Roaring Brook Road Chappaqua, New York

4 Beds 5 Baths 2,875 SqFt 1.02 Acres

This sophisticated four-bedroom residence offers an ideal blend of convenience and tranquility just north of New York City. Enjoy the ease of walking to the vibrant village of Chappaqua—with its boutiques, cafés, and train station—while benefiting from the highly regarded Pleasantville School District. Commuting is effortless with the Chappaqua station mere minutes away and seamless access to the Saw Mill Parkway. An evening on Broadway is just a train ride away, with the serenity of home awaiting your return.
The home’s thoughtful layout begins with a welcoming entry that flows into a beautifully renovated kitchen, where a center island anchors the space. Designed with a nod to California bungalow charm yet updated with modern finishes, it sets the tone for comfortable, stylish living. At the rear of the home, a luminous family room with vaulted ceilings provides an airy, sunlit retreat, ideal for both relaxation and entertaining.
Upstairs, four generously proportioned bedrooms offer privacy and comfort. The principal suite, discreetly positioned in its own wing, affords a peaceful escape from the bustle of daily life, while the remaining bedrooms accommodate family or guests with ease. Beyond the interiors, a private, low-maintenance backyard extends the living space outdoors.
With its prime location, modern updates, and seamless lifestyle, this residence presents a rare opportunity to step effortlessly into Westchester living. Full bus service to Pleasantville schools further enhances its appeal.

$1,325,000 Pending

260 Mill River Road Chappaqua, New York

4 Beds 5 Baths 3,561 SqFt 2.71 Acres

Set on a quiet cul-de-sac, this charming 3-bedroom Cape, which could live like a 4-bedroom, offers the perfect blend of comfort, convenience, and style. The home has been impeccably maintained and thoughtfully renovated, with updates that make it truly move-in ready.
From the moment you arrive, the curb appeal stands out, enhanced by updated landscaping and a freshly painted exterior. Inside, natural light fills every room. The main level offers a primary bedroom and a flexible office/den, while upstairs provides spacious additional bedrooms and beautifully renovated full bath.
Enjoy entertaining or relaxing outdoors with a slate patio and a stunning pool, ideal for summer gatherings. A whole-house generator, newer roof, and central air provide ease of living, while the finished basement with full bathroom offers space for recreation, work, or guests.
Perfectly situated within walking distance to town, schools, shops, parks, and train, this home offers both privacy and community — a rare find in such a convenient location.

$1,299,500 Active

36 Pond Hill Road Chappaqua, New York

3 Beds 4 Baths 2,866 SqFt 1.43 Acres

AO as of 9/29. Beautifully sited on a lovely & picturesque acre plus of perfectly flat property on a highly desirable street in the Chappaqua school district, this gracious colonial lives like a four bedroom home. The first floor boasts a formal dining room and living room with oversized windows, a combination eat in kitchen (renovated 2019) and family room with a wood burning fireplace and sliders to the yard, renovated powder room mud room with laundry and garage & driveway access. The upstairs living space features a primary bedroom with en suite bathroom, two bedrooms, a bonus room with a door & closet and full hall bathroom with tub/shower combination. Hardwood floors flow throughout with the exception of one of the bedrooms. The 1000 sq ft unfinished lower level (not included in total s.f) can be an incredible playroom/recreation room when finished and offers an abundance of storage. The stunning open kitchen with custom Coline cabinetry, quartz countertops and breakfast bar seating, recessed lighting and pantry cabinets is a highlight. Improvements made after 2018 include a new roof, boiler and hot water heater. All bathrooms have been completely renovated in the recent years. This meticulously maintained and quality built home with very low taxes situated in a neighborhood that is ideal for biking/walking/play and a picture perfect piece of property is a combination not to be missed!

$1,299,000 Pending

41 Valley Lane Chappaqua, New York

3 Beds 3 Baths 2,034 SqFt 1.19 Acres

Nestled in a tranquil cul-de-sac, this captivating single-family home effortlessly combines historical charm with modern amenities. Set on a third of an acre with lush, mature landscaping for beauty and privacy, the property also features a fenced yard—an ideal space for pets, play, or outdoor relaxation. The antique home, distinguished by its high ceilings and vintage architectural details, welcomes you with a classic front porch, inviting you to appreciate its timeless appeal.

Inside, the residence features an elegant entrance foyer that leads to a spacious, light-filled formal dining room, perfect for entertaining. The chef’s kitchen is a culinary enthusiast's dream, equipped with granite countertops, a sizable kitchen island, and ample pantry space for all your storage needs. Two and a half well-appointed bathrooms serve the home, offering convenience for family and guests alike.

The home boasts four generously sized bedrooms, including a luxurious primary bathroom that provides a serene retreat. Each room reflects the property’s history while accommodating a modern lifestyle. Ample storage throughout ensures functionality without compromising on the aesthetic integrity of this antique gem.

This property offers a unique opportunity to own a piece of history complemented by today’s comforts, making it an ideal sanctuary for those seeking both elegance and practicality.

$1,250,000 Pending

59 Crest Road Chappaqua, New York

4 Beds 3 Baths 2,550 SqFt 0.33 Acres

Tucked back on a private corner lot on one of Chappaqua’s most desirable and quiet streets, this expanded mid-century ranch offers a rare opportunity to create your dream home in an award-winning school district. The property is well situated on the lot, leaving plenty of space for a pool or future outdoor expansion.

Inside, the home offers a light-filled layout with generously sized rooms, walls of windows, and a natural flow between indoor and outdoor spaces. The kitchen opens to a large living and dining area anchored by a slate-surround fireplace and wide views of the level, park-like backyard. French doors lead to a deck and stone patio—ideal for relaxing or entertaining.

A spacious great room with wood-burning stove and powder room adds flexibility for everyday living. The main level also features an ensuite bedroom with glass doors to the yard, along with two additional bedrooms and a full hall bath. Upstairs, you'll find another bedroom, a full bath, a study, and a bonus room—offering a flexible layout that lives like a 5+ bedroom home.

The current owners have already begun the process of restoring and upgrading the home, and it’s ready for its next chapter. With potential for reconfiguration or expansion (with approvals), this is a smart value opportunity in a location where homes are rarely available at this price point.

Just minutes from the train, town, schools, Whole Foods, and Lifetime Fitness, this peaceful and private retreat offers convenience without compromise.

$1,200,000 Pending

6 Algonquin Drive Chappaqua, New York

4 Beds 4 Baths 3,776 SqFt 1.22 Acres

Step into this beautifully updated 4-bedroom, 2.5-bathroom home, just a short stroll from the vibrant shops, dining, and charm of downtown Chappaqua. Perfectly situated for an easy city commute, this home offers the ideal blend of convenience and tranquility. Inside, you'll find generously sized rooms filled with natural light. The serene primary suite provides a peaceful retreat at the end of the day and features a walk-in closet and private bathroom with double vanity. Gorgeous refinished hardwood floors flow throughout, complemented by fresh, professional painting that brings a modern, cohesive touch. The family room, adorned with warm antique barnwood from a Pennsylvania farm, offers a cozy, cabin-like ambiance—perfect for relaxing or entertaining. An attached garage provides ample space for storage and vehicles, ensuring comfort and practicality.
Don't miss this unique opportunity to own a move-in ready home in one of Chappaqua’s most desirable locations.

$1,200,000 Pending

21 Kipp Street Chappaqua, New York

4 Beds 3 Baths 2,447 SqFt 0.66 Acres

Welcome to 26 Kings Court, Chappaqua, a storybook, village Colonial enchantingly set among towering trees on a quiet cul-de-sac just a short stroll to schools, shops, town and train. If your Brooklyn brownstone could move to the suburbs, this would be it. Regal, barrel-vaulted front portico. Welcoming front entry. French doors introduce the gracious front-facing living room warmed by morning sun and a wood-burning fireplace and accented with built-in cabinetry and hardwood flooring. Adjoining is a traditional formal dining room with chair-rail molding and hardwood flooring. Afternoon sunshine streams into the wonderful white, designer kitchen outfitted with high-end, stainless-steel appliances from Wolf, Sub-Zero and Bosch, and anchored by a large center island with striking butcher block top and breakfast bar. A French door to the deck makes for easy BBQ and alfresco dining. Retreat to the coziness of the sunroom, illuminated by natural light on three sides. Comfort abounds throughout the four, upstairs bedrooms, including the primary with its own sitting/dressing area and private ensuite bath, and in the updated hall bath with marble tile and shower over jetted bathtub. An unfinished, walk-up attic adds more charm and storage. The basement is unfinished and houses laundry, mechanicals and storage. A convenient side entry connects to a flat driveway leading to a detached garage with a separate studio offering flexible space for home office, exercise, or more introspective pursuits. Lush landscaping and lovely yards envelope the residence. A quintessential Chappaqua Colonial.

$1,159,000 Pending

26 Kings Court Chappaqua, New York

4 Beds 3 Baths 2,060 SqFt 0.39 Acres

A dramatic and stunning four-bedroom Contemporary home set on 1.2 professionally landscaped acres, designed by Jan Johnsen, former landscape architect for the New York Botanical Gardens. Surrounded by wooded privacy, this serene setting features two separate decks and a ground-level patio that surrounds the exterior of the home. Inside, this home offers a light-filled, modern, and open layout with a seamless connection to nature through its soaring ceilings, skylights, and windows. The main living area features both living and family rooms, separated by a custom wood-burning fireplace and dual access to the large deck that runs along the side of the house. The eat-in kitchen is outfitted with heated floors, soapstone countertops, stainless steel appliances, and direct access to a second deck, ideal for grilling or your morning coffee. A formal dining room, two-story entry foyer, powder room, and a convenient laundry area with patio access complete the first floor. Upstairs, the primary suite includes a walk-in closet and a completely renovated en-suite bath. Three additional bedrooms and another full bath. Additional highlights include hardwood floors, modern brushed nickel switch plates, upgraded interior doors, and modern lighting. Nest cameras and thermostats, roof and skylights (2021). The unfinished basement provides storage or potential for future customization, with direct access to a two-car garage. Located near schools, shops, and just a short drive to the Chappaqua train station, this home offers a rare combination of privacy, space, and modern comfort.

$1,150,000 Pending

569 Millwood Road Chappaqua, New York

4 Beds 3 Baths 3,264 SqFt 1.26 Acres

Move right into this beautifully updated three bedroom, two bathroom ranch, perfectly situated within the award-winning Chappaqua school district. Thoughtfully renovated from top to bottom, this home offers modern comfort and timeless charm. The heart of the home is the stylish kitchen featuring classic oak cabinetry, sleek quartz countertops, and ample space for cooking and entertaining. Both bathrooms have been fully renovated with fresh, contemporary finishes. Enjoy cozy evenings by the fireplace in the spacious living room, and retreat to one of the generously sized bedrooms for quiet relaxation. Step outside to a flat, private yard—ideal for play, gardening, or hosting gatherings on the patio. This turn-key home offers the perfect blend of convenience, comfort, and location. Don’t miss this exceptional opportunity to live in a move-in ready home with top-tier schools and suburban tranquility.

$1,099,000 Active

10 Barnes Lane Chappaqua, New York

3 Beds 2 Baths 1,776 SqFt 0.8 Acres

Striking frame and brick-front split-level. Welcoming front-deck. Grand and gracious living room richly adorned with a brick-front, wood-burning fireplace, built-in cabinetry, hardwood flooring, recessed lighting, and three front-facing, sliding glass doors to the deck, which illuminate the space in natural light, let gentle breezes cool the space, and provide easy access for indoor/outdoor living. Cater formal occasions in the front-corner, formal dining room, adjoining the living room and the eat-in kitchen, outfitted with stainless steel appliances, wood cabinetry, tile backsplash, and granite countertops. Grow and pick fresh herbs right from the box-type, greenhouse window over the kitchen sink. Dine casually in the open, airy, atrium-like breakfast room, with ceiling fan, large wall of windows, and slider to the new, generously proportioned bluestone patio for easy alfresco dining. The main-level home office is a flexible space for work, study or relaxation. Completing the main level, off the kitchen is a laundry/mud room with a door to the side yard. Upstairs reside three bedrooms and two full bathrooms, including a primary suite with walk-in closet and its own private bath ensuite, two spacious, front-facing bedrooms, both with outfitted closets and hardwood flooring beneath wall-to-wall carpeting, an updated hall bath with beadboard wainscoting, a natural stone-topped vanity and a shower over bathtub, and a large, cedar hall closet. Sitting downstairs is an inviting family room with large, front- and side-facing windows, a ceiling fan, recessed lighting, hardwood flooring and a side-entry door for easy indoor/outdoor access. Garage access is also on this level. The front deck and the new, rear, generously proportioned bluestone patio both provide enjoyable options for outdoor settings, including viewing the old growth trees and established landscaping surrounding the property, which is nicely accented with new bluestone pathways and outdoor landscape lighting. Plus, easy access to schools, and a central Chappaqua location.

$1,075,000 Pending

495 Quaker Road Chappaqua, New York

3 Beds 2 Baths 2,695 SqFt 1.157 Acres

AO 9/23/25. Set on 3.25 private acres of lush formal gardens and mature woodlands, this one-of-a-kind Chappaqua residence is a rare architectural treasure. Designed in the 1930s by renowned Westchester architect James Renwick Thomson, the home blends refined sophistication with warm, inviting charm—offering an unparalleled living experience just minutes from the heart of town. From Palladian windows and vaulted ceilings to Dutch doors, rough-hewn beams, copper gutters and exquisite custom woodwork, every detail speaks to the home's timeless character. Light floods the interiors through bay windows, while a second-floor terrace invites al fresco dining overlooking the serene landscape. Outdoors, the grounds are truly spectacular: meandering pebbled pathways wind through formal gardens with multiple sitting areas, two tranquil koi ponds, and a meandering stream. A red clay tennis court (easily restored) adds a resort-like touch, and the long, private driveway ensures a secluded retreat. Located within the award-winning Chappaqua School District and close to town, train, schools and swim and tennis clubs, this property offers both privacy and practicality. Commuting to NYC is a breeze—just a short drive or train ride away. Low taxes. DRIVEWAY ON TURNER DRIVE. Timeless Elegance Meets Tranquil Living - Don't miss this unique offering!

$999,000 Pending

124 Seven Bridges Road Chappaqua, New York

3 Beds 2 Baths 1,918 SqFt 3.25 Acres

$849,000 Active

73 S Bedford Road Chappaqua, New York

4 Beds 3 Baths 1,584 SqFt 0.26 Acres

$799,000 Active

5 Grove Mews Chappaqua, New York

2 Beds 3 Baths 1,500 SqFt

Charming and lovingly maintained cape cod home on beautiful private property. Located in the sought after Chappaqua Ridge neighborhood ,this home offers town water, sewer and natural gas, and is minutes to town, train and schools. The first floor features an open kitchen/dining/ living room plus 2 bedrooms and a bath. One of the bedrooms could also be used as a home office. There are sliders out to an expansive deck overlooking the picturesque property. Upstairs has 2 additional nice sized bedrooms and a hall bath. The kitchen, bathrooms and windows have been updated, and there are hardwood floors under the carpets. Automatic generator.The fenced rear yard has been lovingly tended to by the owners, showcasing specimen trees, flowering perennials and plenty of flat yard to play. This home is lovely and charming as is, or has great potential for an addition/renovation.

$799,000 Pending

37 Hollow Oak Road Chappaqua, New York

4 Beds 2 Baths 1,420 SqFt 0.31 Acres

Experience the vibrancy and user-friendly vibe of the Hamlet of Chappaqua in this very special move-in ready, end-unit townhouse, which could be the one you’ve been waiting for. Perfectly located, it is walkable to train, schools, restaurants, shops, farmer’s market, town hall, library and more. It offers generous space with flexibility of use featuring two large bedrooms, plus loft, lower level flex room and 2 1/2 baths. There are fabulous hardwood floors on both the first and second levels -- oak with cherry stain on the first and beech wood on the second. After entering through a rocking chair, covered front porch, the main floor features a considerable entry hall, powder room, renovated dine-in kitchen with bay window and pantry, newer stainless steel appliances, and new silestone counters and backsplash. The expansive, sun-filled dining area flows seamlessly into the living room, showcasing an elegant wood burning fireplace and custom built-in shelving. A sliding glass door leads to a private deck. The second floor has a sizable primary suite with great closet space and a nicely updated bath. The second bedroom is very spacious. A large loft area is currently used as an office but could be used as a media or guest space depending on your needs. A modern hall bath completes the second floor. The basement offers an additional 531 square feet (not included in the 1767 total square footage). This area features a flex room, a huge laundry room, amazing storage space and access to the garage. Leafy front and side yards with two gardens of eco-friendly native plants and designated as "pollinator pathway" are unique to this unit. One car garage plus two additional parking spaces (driveway and carport) are also unique to this unit. This townhouse is truly a “must see.” It is no wonder that this was the builder’s model!

$799,000 Pending

149 King Street 4 Chappaqua, New York

2 Beds 3 Baths 1,767 SqFt 0.03 Acres

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

$799,000 Active

249 Mill River Road Chappaqua, New York

4 Beds 2 Baths 2,100 SqFt 0.45 Acres

$799,000 Pending

816 Hardscrabble Road Chappaqua, New York

3 Beds 2 Baths 1,660 SqFt 0.58 Acres

Accepted offer 8/19 Inspections scheduled 8/20 Showing for back-ups only.
Discover exceptional living in this well maintained 2-bedroom, 2-bath townhome.
A true gem within Chappaqua's coveted Old Farm Lake community.
Enjoy lake views from your back deck or use the electric roller shades for the living room view.
This unique unit boasts a front lawn, inviting patio, and lush landscaping overlooking a picturesque pond.
The kitchen features new appliances, complementing the peace of mind offered by a new furnace and AC with whole-house air purifier.
The master suite offers a walk-in closet and a spacious bathroom.
The second bedroom features clever built-ins perfect for a desk space.
The finished basement provides versatile bonus space for a home office or gym.
Experience the best of Old Farm Lake at the club house, gym, pool, tennis courts, paddle tennis, basketball, and beautiful grounds.
Close to shopping, schools, and highways.

$775,000 Pending

77 Further Lane Chappaqua, New York

2 Beds 2 Baths 1,549 SqFt 0.01 Acres

Beautifully updated 2-bedroom, 2.5-bath townhouse in the desirable Old Farm Lake community. The open layout features new hardwood floors on the main level, freshly painted interiors, and renovated baths. Upstairs offers two generous bedrooms with ensuite baths, including a primary suite with ample closet space and an updated bath. Relax on your private patio with lake views and enjoy community amenities—pool, tennis, basketball, clubhouse, and fitness center. With low taxes and a prime Chappaqua location near schools, shops, and train, this home is a must-see!

$745,000 Pending

30 Rambling Brook Road Chappaqua, New York

2 Beds 3 Baths 1,244 SqFt 0.01 Acres

$699,000 Active

10 Grove Mews Chappaqua, New York

2 Beds 3 Baths 1,479 SqFt

This charming cottage has been completely reimagined, seamlessly blending timeless character with modern luxury. Fully gut-renovated and thoughtfully redesigned from top to bottom, this inviting home offers the perfect retreat—whether you're seeking a serene weekend escape or a full-time residence.
Ideally located just minutes from downtown Chappaqua and seconds from Chappaqua Crossing, Horace Greeley High School, and Whippoorwill Park, the convenience is unmatched.
Inside, the sun-drenched interior features an open layout with high-end finishes throughout. The custom kitchen (2018) is outfitted with sleek appliances and tailored cabinetry, while the beautifully updated bathrooms exude style and sophistication. Cozy living spaces and gorgeous hardwood floors enhance the home’s warmth and character. Every detail has been carefully curated, including updated systems and new windows, all while preserving the home’s original charm.

$600,000 Pending

380 Whippoorwill Road Chappaqua, New York

3 Beds 2 Baths 880 SqFt 2.29 Acres

$599,000 Active

150 Bedford Road 12A Chappaqua, New York

2 Beds 2 Baths 924 SqFt 0.001 Acres

Major Renovation required.Property being sold As Is. Verify Taxes with municipality. Price includes New Construction and Engineering Plans with Clean Asbestos Abatement Certificate. Underground Oil Tank has been removed with a Clear D.E.C; Certificate.

$599,000 Active

1008 King Street Chappaqua, New York

1 Beds 2 Baths 1,052 SqFt 0.99 Acres

Location, Location, Location! Chestnut Oak Complex. Dramatic and bright townhouse with natural lighting. This 1 bedroom 1.1 bath plus huge Loft/Den is in mint condition. Updated kitchen with stainless-steel appliances. Living room with high ceilings, fireplace and wall of windows is combined with spacious dining area. Updated powder room on the first level. Huge primary bedroom with with two clothes closets and private updated full bath. Loft/Den/Office off primary bedroom with sliding glass door to balcony. This unit comes with one-car garage, newer furnace, hot water heater, refrigerator. Washer and dryer in the unit. Entire interior of the unit was just painted (September 2025). Complex offers, pool, tennis and community garden. Conviently located to Chappaqua train station, shopping, schools, parkways and bus.

$539,000 Active

356 North Greeley Avenue Chappaqua, New York

1 Beds 2 Baths 1,207 SqFt 0.15 Acres

Chappaqua, N.Y.

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