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$2,250,000
4 Beds ⋅ 6 Baths ⋅ 1025674 MLS
A rare opportunity to own a private mini-estate on approximately 6.9 acres in Millwood. The main residence offers four bedrooms, three-and-a-half baths and generous living spaces with views of the property’s natural surroundings. Highlights include an eat-in country kitchen with French marble flooring, a living room overlooking the pond and waterfall, multiple fireplaces, radiant heat in the primary bath and extensive closet storage. The property also includes a renovated guest cottage above a three-car garage, plus an additional three-car garage with a private retreat or meditation room featuring pine paneling and a stone fireplace. Outdoor amenities include a heated in-ground concrete pool, pond, waterfall, landscaped gardens, specimen plantings and a three-hole golf course. A distinctive property offering privacy, flexible space and a peaceful setting within the Chappaqua School District. Stay tuned coming soon!

82 Shingle House Road, Millwood
$1,995,000
4 Beds ⋅ 3 Baths ⋅ 882412 MLS
Nestled on a picturesque tree-lined street in the highly sought-after Chappaqua School District, this beautifully renovated 4-bedroom Colonial combines timeless charm with thoughtfully updated living spaces. A welcoming front porch offers the perfect place to enjoy a quiet morning coffee or relax on a summer evening. A gracious entry foyer introduces the home's warm and inviting interior. The sun-filled living room features oversized windows, custom built-ins, and elegant proportions, creating a comfortable space for everyday living and entertaining. At the heart of the home is the beautifully renovated chef's kitchen with top of the line stainless appliances, designed for both function and style, with a spacious center island with seating, a sunny dining area, built-in desk, generous walk-in pantry, and access to the deck for seamless indoor-outdoor living. Just beyond the kitchen, the inviting family room is anchored by a raised-hearth wood-burning fireplace, offering a warm and comfortable gathering space. The first floor also includes a formal dining room and a versatile room with walls of windows, ideal as a second family room, home office, playroom, or sunroom, a full bath and laundry room. Upstairs, the primary suite has a renovated bath and large walk-in closets. Three additional bedrooms share a well-appointed hall bath, providing ample space for family and guests. The expansive lower level offers exceptional storage and outstanding potential for future finished recreation, fitness, or media space. Throughout the home, rich hardwood floors, custom millwork, abundant natural light, and a thoughtfully designed open floor plan create an atmosphere that is both elegant and welcoming. Ideally located in one of Chappaqua's most desirable neighborhoods, this is a home that offers timeless appeal, exceptional comfort, and a setting you'll enjoy for years to come. A must see home!!

12 Brandon Drive, Mount Kisco
$549,000
2 Beds ⋅ 1 Baths ⋅ 993303 MLS
Opportunities like this do not come around often in Chappaqua, and when they do, they tend to move quickly. What is being offered at 58 Maple Ave is a flat, level, in-town parcel with an existing 2-bedroom, 1-bath cottage set back from the road among towering pines, in one of Westchester County's most coveted villages. Whether a buyer chooses to develop the land, renovate what is there, or simply occupy the existing structure while planning next steps, the opportunity here is defined first and foremost by the location and the lot. The cottage itself, built in 1930 and totaling 711 square feet, is being sold strictly as-is. It sits on a 0.28-acre lot with driveway parking and includes a front deck, a patio, and a yard with a quiet, private feel that genuinely surprises you given how close you are to the center of town. Inside, the main level includes a great room with cathedral ceilings and built-in features, a kitchen, two bedrooms, and a full bath. A partial basement with Bilco door access houses laundry and mechanicals. The structure has a history as a consistently rentable asset in a market where rental demand is strong and vacancy is rare, which speaks to the enduring appeal of this particular address regardless of what a future owner ultimately decides to do with it. The location is the defining feature and the reason this property commands the attention it does. You are minutes on foot from the Chappaqua Metro-North Station, putting Midtown Manhattan within comfortable commuting distance without the stress of a car or a parking lot. The village's boutique shops, restaurants, and parks are equally walkable, giving this address an everyday livability that most Westchester properties simply cannot replicate. For those who travel frequently for business, Westchester County Airport is also easily accessible. This is a genuinely rare convergence of walkability, transit access, and village character that defines the upper end of what Chappaqua real estate has to offer. The property falls within the Chappaqua Central School District, one of the most highly regarded public school systems in New York State and a consistent driver of demand in this market. Flat lot, set-back privacy, walk-to-train location, and Chappaqua schools.

58 Maple Avenue, Chappaqua
$3,100,000
5 Beds ⋅ 6 Baths ⋅ 990281 MLS
Privately gated and masterfully crafted, this exceptional custom brick estate is a showcase of timeless elegance and grand-scale living, nestled on over two acres in the heart of Chappaqua. Beyond the cobblestone apron and curbing, a sweeping driveway leads to a residence designed for both luxury and comfort, boasting soaring 10-foot ceilings, four stately fireplaces, exquisite architectural detail, and refined finishes throughout. Enter through a breathtaking grand foyer, where gleaming hardwood floors with intricate wood inlay medallion set the tone, and a dramatic three-story suspended spiral staircase anchors the home in architectural splendor. The main level is ideal for entertaining, offering a formal living room, formal dining room, an expansive family room with a custom bar, and seamless access to a private bluestone patio, perfect for indoor-outdoor gatherings. The chef’s kitchen is a culinary masterpiece, featuring high-end appliances, breakfast area, butler’s pantry, and dual access points to the patio. A main-floor guest/au pair suite, private office or den, and powder room complete the level. Upstairs, the serene Master Suite is a retreat unto itself, complete with a sitting area, dual walk-in closets, and a spa-like marble bath with heated towel racks, dual vanities, clawfoot soaking tub, and an oversized glass shower. Three additional generously-sized bedrooms, one with an ensuite, and a full hall bath, along with a dedicated laundry room, offer both comfort and convenience. The third floor adds a spacious game and media room, while the walk-out lower level features a gym, mudroom, recreation space, sitting area, and access to the beautifully landscaped backyard. Outside, enjoy artisan stonework, multiple patios, a gazebo, hot tub, built-in BBQ station, and lush, level grounds ideal for entertaining and play. Three heated garages, including an electric vehicle charging station, complete this extraordinary masterpiece with modern convenience and sophistication. Located just minutes from Chappaqua’s charming village center, award-winning schools, fine dining, shopping, Mt. Kisco Country Club, Metro North, and major highways. This is a a rare opportunity to own one of Chappaqua’s most distinguished estates, an architectural triumph of timeless sophistication and commanding presence, set within one of Westchester’s most coveted communities.

2 Heathcote Drive, Mount Kisco
$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
$989,000
3 Beds ⋅ 2 Baths ⋅ 1004970 MLS
Best value in the Award Winning Chappaqua School District! Set on an acre in the desirable Rolling Fields neighborhood, this well maintained home offers comfortable living with a flexible layout that lives larger than its 3-bedroom configuration. Updated in 2013 with, new roof, new windows, new mechanicals, kitchen and bath renovations. The main level features an inviting kitchen with stainless steel appliances and granite countertops, open to the dining area for easy everyday living and entertaining. Hardwood floors run throughout the main floor of the home, and the spacious living room has a wood-burning fireplace. The primary bedroom includes an en-suite bath, while the layout offers the convenience of no stairs from the front entry to the main living areas and bedrooms. Additional space in both the lower level and attic provides exceptional flexibility for future expansion. The home also includes both a detached two-car garage and an attached one-car garage for a total of three garage spaces. Enjoy a wonderful combination of location, functionality, and future potential, ideally situated close to Chappaqua and Mount Kisco town centers, Metro-North train service to NYC, shopping, dining, schools, and everyday conveniences, with additional room for future expansion.

10 Horseshoe Road, Mount Kisco
$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
$2,990,000
6 Beds ⋅ 6 Baths ⋅ 909816 MLS
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.

20 Bessel 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.