Chappaqua Real Estate

Welcome to Chappaqua, New York—a charming hamlet nestled in the heart of Westchester County. Known for its picturesque landscapes and tight-knit community, Chappaqua offers an idyllic suburban lifestyle just a stone's throw away from the bustling energy of New York City. This vibrant town is characterized by its tree-lined streets, historic homes, and a rich tapestry of local culture that seamlessly blends modern amenities with small-town charm.

Chappaqua is renowned for its top-notch schools, making it an ideal destination for families seeking quality education. The town's commitment to excellence in academics is evident in its highly rated public schools, which consistently rank among the best in the state. Beyond education, the community is vibrant with local shops, gourmet eateries, and recreational parks, providing residents with an abundance of leisure activities.

Nature enthusiasts will appreciate the scenic beauty that surrounds Chappaqua. With its proximity to the breathtaking Rockefeller State Park Preserve, residents can enjoy hiking, biking, and tranquil walks amidst stunning natural landscapes. The town also hosts a variety of community events throughout the year, fostering a sense of belonging and camaraderie among residents.

Moreover, Chappaqua's convenient location offers easy access to major highways and the Metro-North train line, making commuting to Manhattan a breeze. Whether you're a first-time homebuyer or looking to relocate, Chappaqua presents a unique blend of suburban serenity and urban convenience. Discover the charm of Chappaqua, where community spirit thrives and every day feels like a breath of fresh air.

Newest Listings in Chappaqua

$1,800,000

4 Beds ⋅ 4 Baths ⋅ 1044050 MLS

Welcome to this beautifully maintained almost 3000 sq ft 4 bedroom 4 bath Colonial set on a private, sun-filled one acre property framed by mature trees, a classic stone wall , and meticulously maintained landscaping and plantings. Elegance and craftsmanship are evident throughout with beautiful hardwood floors, generously sized bedrooms and a primary suite with private en-suite bath. At the heart of the home, the kitchen opens to an inviting sitting room with a gorgeous stone fireplace and double doors leading to a seamless indoor-outdoor living experience. The finished walkout lower level offers exceptional additional living and entertaining space, complete with a bathroom and built-in ceiling speakers (with surround sound), plus direct access to the grounds and pool area. Outside, enjoy your own private retreat featuring a 40' X 16' heated in-ground fiberglass pool with sunning deck and full Certificate of Occupancy along with a new patio and fire pit under the deck. The pool is professional maintained weekly, and the propane tanks for the pool heater were recently filled. Additional improvements include a freshly painted exterior and deck (August 2026), new hot water heater and refrigerator (2024), septic cleaning (June 2026)and an EV charging port in the two-car garage. There is an alarm system in place. Thoughtfully maintained and move-in ready, this home combines timeless craftsmanship, modern conveniences, and resort-style indoor-outdoor living in a beautiful and private setting.

406 Bedford Road, Chappaqua

$1,325,000

3 Beds ⋅ 3 Baths ⋅ 1040629 MLS

A private drive leads to your own secluded oasis. 35 Marcourt is a picture perfect colonial tucked away in a peaceful wooded setting located in the coveted Dodge Farm neighborhood. This home is filled with character, charm and architectural details making it one-of-a-kind. The classic center hall opens to both the formal dining room and a living room with a beamed ceiling, custom built-ins and a wood burning fireplace. Spectacular family room is flooded with light from skylights in the cathedral ceiling, three walls of windows and doors to the patio. A bright kitchen opens to the back porch overlooking the rear yard and adjacent to a brick patio with a built-in grill. An added bonus on the first floor is a den/office or guest suite with a beamed ceiling, built-in bookshelves and en-suite bath. Upstairs is a primary bedroom and bath, two bedrooms with double exposures and a hall bath. This home is a move-in ready gem just minutes from the village and train.

35 Marcourt Drive, Chappaqua

$1,665,000

1038452 MLS

Extremely rare and ultra-private 12.92 acres of waterfront land in the Whippoorwill Lake enclave of Chappaqua. An exceptionally private canvas for a one-of-a-kind secluded getaway compound. Beyond the gate, a long private drive ascends to a concealed building site with sweeping lake and woodland vistas, plus natural water features including a waterfall and bridge. Near Whippoorwill Park, Chappaqua’s largest preserve (169 acres) and adjoining other protected woodlands. Minutes to Chappaqua, Armonk, and Mt. Kisco, express NYC commute and just 15 minutes to Westchester County Airport. Choice of Chappaqua or Armonk schools. The land sits within the Croton Watershed. An optional, stunning modern architectural package designed specifically for the site to maximize bucolic views. Full plan set and renderings available under separate agreement ($250,000). A truly one-of-a-kind and rare offering. Showings by appointment only for discerning, qualified buyers with verified proof of funds. Ideal for those seeking to build a custom private compound or a bespoke retreat.

767 King Street, Chappaqua

$1,590,000

3 Beds ⋅ 3 Baths ⋅ 1017997 MLS

Charming Expanded Colonial in the Heart of Chappaqua - New 4 bedroom Septic, 2024 Roof and Exceptional Indoor/Outdoor Living. Beautifully renovated and expanded Colonial offering 2,690 Square Feet of sophisticated living, a flexible first-floor guest/au pair suite, chefs kitchen with Wolf appliances, private primary suite, 2 fireplaces, expansive deck and mature grounds backing to protected green space. Just moments to Chappaqua village, Metro North and highly regarded Chappaqua schools. Enter into this enduring Colonial blending elegance with today's lifestyle. A welcoming foyer opens to a gracious living room and fireplace. A formal dining room with a tray ceiling. Timeless appointed chefs eat-in-kitchen 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 and a coffered ceiling. The sunroom offers custom built-ins and an abundance of natural light. A first floor au pair/guest/office and full bathroom. Upstairs is the primary bedroom with high ceilings, walk-in custom closet, private study with built-ins, and en-suite bath with double sinks, marble shower and whirlpool tub. 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.

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

$1,849,000

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

$839,999

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

$849,999

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

$2,249,000

3 Beds ⋅ 4 Baths ⋅ 973551 MLS

Set on beautifully landscaped grounds in one of Chappaqua’s most coveted neighborhoods. This exceptional David Graham-designed 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

$4,500,000

5 Beds ⋅ 7 Baths ⋅ 950756 MLS

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!

150 Old Farm Road N, 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.