Refine Search
Map
Sort by
$1,725,000
4 Beds ⋅ 4 Baths ⋅ 974007 MLS
Welcome to an exceptional move-in ready home located in a highly desirable Chappaqua neighborhood known for its award-winning schools & sought-after lifestyle. Perfectly positioned in a quiet neighborhood, this stunning property offers privacy, space & luxury living at its finest. In addition, easy access to the North County Trail for any outdoor activities of your choice. Step inside & you'll find a bright, open-concept floor plan with natural light & high-end finishes throughout. The eat-in gourmet stylish kitchen is a chef's dream, complete with stainless steel appliances, state-of-the-art cabinetry & a large center island - perfect for entertaining or everyday living. The inviting living room & elegant dining space provide a seamless flow, ideal for gatherings of any size. The upstairs boast 4 spacious bedroom plus an office and bonus space ideal for kids suite or study. The luxurious primary suite includes spa-inspired bathroom, oversized shower, & a generous walk-in closet. Outside, step into your own private oasis designed for ultimate outdoor living with a spacious patio, a 3-season screened in porch & flat backyard. Whether you're a first time home buyer or upgrading, this is a rare opportunity to own a turn-key home in one of Westchester's finest communities. Come visit today!

53 W Orchard Road, 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
$2,400,000
4 Beds ⋅ 4 Baths ⋅ 1042846 MLS
- ELEVATED LIVING, LIGHT-FILLED DESIGN - This home has been transformed through a combination of new construction and thoughtful remodeling, blending classic Colonial proportions with a fresh, light-filled interior built for gracious living and effortless entertaining. The rebuild includes all-new HVAC, plumbing, and electrical systems and a full-house 25kW Generac generator. This lovely residence features 4 well-proportioned bedrooms and 4 bathrooms (3 full, 1 half) thoughtfully arranged across 3 finished levels, including a full lower-level recreation room. The 1st floor and 2nd floor consist of 3,191sq ft of livable space and the finished lower level is another 649 sq ft which gives you 3,840 total livable space to suit your family’s needs. At the heart of the home is a sprawling, sun-drenched great room where kitchen, dining, and family room flow together beneath soaring vaulted ceilings, a true showpiece for entertaining on any scale. The chef's kitchen commands the space with a grand quartzite island large enough to gather a crowd around, a full Thermador appliance suite, and custom Bilotta designed cabinetry, all opening onto a stone fireplace lounge or out to the rear deck for seamless indoor-outdoor living. A series of solar-powered skylights washes the main and second floors in natural light, lending the home an elevated, airy quality, a kind of California-meets-East-Coast serenity rarely found north of the city. For quieter moments, a separate formal living room with French doors offers refined, intimate gathering space, while an attached two-car garage adds everyday convenience. Upstairs, the primary suite delivers a true retreat, with a private sitting area, an oversized walk-in closet, and a spa-caliber bath with a freestanding soaking tub and oversized large glass shower. Three additional bedrooms and a second-floor laundry room complete the level with equal care. Set on an acre of flat, landscaped grounds, the property offers privacy, space, and room to entertain outdoors with space reserved for your growing needs. Architectural details include a considered blend of modern and traditional materials creating exceptional curb appeal and lasting quality. The coveted Millwood location offers the best of community living, with proximity to local shops and restaurants, the Taconic State Parkway, and Chappaqua schools, Westorchard Elementary, Seven Bridges Middle, and Horace Greeley High. At last, your perfect home awaits, where classic architecture meets modern open-plan living in beautiful Millwood. Note: The neighborhood section on Zillow is showing the incorrect neighborhood, house is located at 230 Pinesbridge Road.

230 Pinesbridge Road, Millwood
$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

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.