Chappaqua Real Estate

Welcome to Chappaqua, a picturesque hamlet nestled in the heart of Westchester County, New York. Known for its serene landscapes and vibrant community spirit, Chappaqua offers a unique blend of suburban tranquility and urban convenience, making it a coveted destination for families and professionals alike.

As you stroll through the charming streets of Chappaqua, you'll be captivated by its rich history and stunning architecture. This quaint village is home to a variety of beautiful homes, from historic colonial estates to modern new constructions, all set against a backdrop of lush greenery and scenic parks. The local real estate market is thriving, attracting those who appreciate both the beauty of nature and the comforts of a close-knit community.

Chappaqua boasts excellent schools, including the highly regarded Chappaqua Central School District, which consistently ranks among the top in the state. Families are drawn to the area for its commitment to education, ensuring that children receive a quality learning experience in a supportive environment.

In addition to its family-friendly atmosphere, Chappaqua offers a vibrant downtown area filled with charming shops, gourmet restaurants, and cozy cafés. Residents enjoy a plethora of recreational activities, from hiking the trails of nearby parks to participating in community events that foster a strong sense of belonging.

With its convenient access to New York City via Metro-North Railroad, Chappaqua perfectly balances suburban living with urban accessibility. Whether you’re looking to settle down or invest in a thriving community, Chappaqua is a place where you can truly feel at home. Discover the magic of Chappaqua and experience the lifestyle you've always dreamed of!

Newest Listings in Chappaqua

$1,550,000

3 Beds ⋅ 3 Baths ⋅ 1023910 MLS

1926 Colonial with timeless character on a private and level half-acre, walkable to the train station and village in Chappaqua, NY. Circular driveway and classic curb appeal set the tone; inside, hardwood floors flow through an open, light-filled layout. The kitchen opens to a fireplaced family room with deck access, plus a formal dining room and a living room with its own wood-burning fireplace and screened porch. Upstairs, lives as a four-bedroom layout, the primary suite is a true retreat - en-suite bath with sauna and private balcony overlooking the yard with Koi pond plus an office/den, and a full hall bath. The partially finished lower level adds a playroom, wine closet, and storage. Brand new central air conditioning, plus a gas line on the street, offers possible future conversion.

312 Quaker Road, Chappaqua

$1,590,000

3 Beds ⋅ 3 Baths ⋅ 1017997 MLS

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 bonus room 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.

131 Douglas Road, Chappaqua

$1,594,000

3 Beds ⋅ 3 Baths ⋅ 1013791 MLS

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, 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. The outbuilding / studio can be converted back to a garage. Square footage does not include the studio space.

676 Hardscrabble Road, Chappaqua

$1,998,999

4 Beds ⋅ 4 Baths ⋅ 1011189 MLS

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.

4 Old House Lane, Chappaqua

$1,849,000

1005784 MLS ⋅ 21 BLDG.

Investment opportunities like this rarely become available in Downtown Chappaqua. Welcome to 21 King Street, a rare mixed-use commercial property offering exceptional visibility, convenience, and income potential in one of Westchester's most desirable downtown locations. The building features two street-level retail storefronts and a residential apartment above, creating multiple income streams and long-term investment value. A standout feature is the private rear parking lot accommodating approximately 14 vehicles—an increasingly valuable asset in downtown Chappaqua. In addition to serving the property's tenants and customers, the parking area may offer additional income potential through rental opportunities. The rear lot also presents future upside, as it may provide opportunities for expansion or redevelopment, subject to municipal approvals and zoning requirements. Ideally positioned just moments from shops, restaurants, and the Metro-North train station, 21 King Street benefits from excellent foot traffic and a highly sought-after location. Whether you are an investor seeking diversified income streams, an owner-user looking to establish a presence in Chappaqua, or someone searching for a prime long-term asset, this is a unique opportunity to own a landmark property in the heart of town with both immediate cash flow and future potential.

21 King Street, Chappaqua

$879,000

3 Beds ⋅ 3 Baths ⋅ 1006886 MLS

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.

2 Timberland Pass, Chappaqua

$2,649,000

4 Beds ⋅ 5 Baths ⋅ 998577 MLS

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.

40 Hamilton Drive, Chappaqua

$875,000

4 Beds ⋅ 2 Baths ⋅ 996830 MLS

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 Total Recent 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.

249 Mill River Road, Chappaqua

$2,499,000

3 Beds ⋅ 4 Baths ⋅ 973551 MLS

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.

33 Greenbriar Drive, Chappaqua

$1,590,000

3 Beds ⋅ 4 Baths ⋅ 984583 MLS

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.

17 Lila Lane, Chappaqua

$809,000

4 Beds ⋅ 3 Baths ⋅ 981423 MLS

Welcome home to this well-maintained residence in the heart of vibrant Chappaqua! This 4 bedroom and 2.5 full bathroom house is located in the award-winning Chappaqua school district. Step inside to discover gleaming hardwood floors throughout, a cozy living room with a wood-burning fireplace, and a bright, charming dining room. The kitchen features ample cabinetry, granite countertops, and brand-new stainless-steel appliances. The spacious primary suite, versatile enough to serve as a large family room, includes a walk-in closet and a newly renovated en-suite bathroom. Upstairs, three generously sized bedrooms await, including a second primary suite with a walk-in closet, and a second full bathroom. Additional highlights include a welcoming front porch, expansive attic storage, a full basement with crawl space, and a circular driveway accommodating up to six cars for effortless access. Enjoy summer days in the fenced backyard—perfect for gatherings, gardening, or basking in the sunshine. This prime location is minutes from the Train Station, library, town hall, post office, shops, restaurants, top-rated schools, and easy access to major parkways. Zoned for versatility, this property offers a potential for conversion back to commercial use, for an attorney’s office, dental practice, or other professional ventures in the bustling heart of Chappaqua. Don’t miss your chance to own this delightful home with endless possibilities! The house is no longer furnished as shown in the photos.

73 S Bedford Road, Chappaqua

$639,000

966226 MLS

A rare opportunity to build mixed use consisting of commercial/professional and multi-family with huge income potential. The 1st floor as commercial and the 2nd and 3rd floors residential apartments. An architect has drawn 4 concept plans ranging from commercial space and lobby with (4) 2-bedroom apartments to commercial space and lobby with (6) 1-bedroom apartments. One example: 1st floor commercial/professional space = 500 sf 1st floor lobby = 562 sf 2nd floor 3 residential units = 2,546 sf 3rd floor 3 residential units = 2,5646 sf Each residential apartment = 760 sf Parking spaces = 10 Land in Chappaqua is indeed a rare commodity, especially one with this amount of upside potential - don't miss this unique opportunity. The concept plans are available upon request.

65 S Bedford Road, Chappaqua

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.