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$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
$1,299,000
4 Beds ⋅ 3 Baths ⋅ 1013321 MLS
Set on a level .64-acre property along one of Chappaqua's most sought-after neighborhood streets, 9 Oak Hill Road is a beautifully updated 4-bedroom, 3-bath Raised Ranch that offers spacious, light-filled living in a peaceful natural setting. A covered front porch welcomes you into an entry foyer, where a short mezzanine staircase leads to the main living level. Here, a gracious living room with a picture window flows effortlessly into the adjoining dining room, creating an inviting space for everyday living and entertaining. Adjacent to the dining room, the eat-in kitchen completes the home's open, functional layout. Oversized windows at both the front and rear fill the living areas with natural light, while the property's exceptional setting—backing to the Saw Mill River Audubon Society's Cameron-Murfeldt Sanctuary—offers privacy, scenic views, and a charming pond that enhances the tranquil landscape. The eat-in kitchen is thoughtfully designed with white cabinetry, stainless steel appliances, a picture window, and a sun-filled breakfast area that enjoys morning light. A door opens directly to the deck, making outdoor dining and weekend barbecues effortless. Three well-proportioned bedrooms are located on the main level, including a spacious primary suite with two closets and a private bath. A corner bedroom enjoys windows on two sides, while the third bedroom features two front-facing windows and a generous double closet. Every bedroom in the home is outfitted with custom California Closets, providing beautifully designed, highly functional storage and organization. The finished walk-out lower level provides exceptional additional living space with a generously sized family room featuring hardwood floors, a decorative electric fireplace, and sliding glass doors that open to the patio. A private, expansive fourth bedroom with hardwood floors and a double closet, a full bath with shower, laundry area, utility room, abundant storage, and direct access to the attached two-car garage complete this versatile level. Set back from the road with a level driveway and expansive front lawn, this inviting home offers the perfect balance of comfortable living, effortless entertaining, and the peaceful beauty of its park-like surroundings.

9 Oak Hill 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
$2,699,000
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
$2,895,000
4 Beds ⋅ 6 Baths ⋅ 992104 MLS
Exceptional new construction opportunity in the highly sought-after Chappaqua School District, currently being built with anticipated completion this Fall 2026. Early buyers will have the rare chance to customize many of the final finishes and tailor the home to their personal style. This thoughtfully designed home offers 4 bedrooms and 5.1 bathrooms, with a highly desirable layout that lives like a larger home thanks to additional flexible living spaces. The main level features an open-concept design with seamless flow between the kitchen, dining area, and informal living room with fireplace. The kitchen is equipped with a premium Thermador appliance package and includes sliding glass doors leading to the back patio, while the family room also features sliders to the covered patio—creating a seamless connection and the perfect setting for indoor-outdoor entertaining. In addition to the formal dining room, formal living room, and powder room, the main level also includes a versatile room adjacent to a full bathroom, ideal for use as a private office, den, or guest accommodations. The fully finished walk-out lower level adds substantial additional living space, including an additional room with sliding glass doors and access to a full bathroom—well-suited for a variety of uses including extended living, recreation, or work-from-home needs. The primary suite is a true retreat, showcasing a tray ceiling, two oversized walk-in closets, and a luxurious bathroom with double vanity, soaking tub, separate shower, and private toilet room. A second-floor laundry room adds everyday convenience. Just a few additional highlights include 9-foot ceilings throughout, 4" oak hardwood floors, high-end finishes across all levels, an oversized two-car garage leading to a mudroom with custom cubbies and closet, a high-efficiency heat pump and cooling system, pre-wiring for a future electric vehicle charging station, and a security system. Privately set on over an acre of land on a cul-de-sac street and surrounded by mature trees, this home offers a peaceful setting while remaining close to parks, town, schools, and transportation. A rare opportunity to own a brand-new, thoughtfully designed home with exceptional flexibility in an ideal Chappaqua location.

39 Barnes Lane, 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

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.