Refine Search
Map
Sort by
$2,950,000
6 Beds ⋅ 6 Baths ⋅ 1035591 MLS
An extraordinary original Myron Goldfinger commission, documented in the architect’s archive as the 1991 Leff Residence, Architecture in the Landscape #7. This exceptional 8,200-square-foot contemporary residence showcases Goldfinger’s signature geometric design, dramatic curved ceiling, sculptural floating staircase, and expansive walls of glass that connect the interiors to the surrounding landscape. Six bedrooms and five-and-a-half baths include an exceptional main-level primary suite, offering a private retreat with a spectacular boutique-style walk-in dressing room featuring multiple custom closets, thoughtfully designed storage, and dedicated display spaces for shoes, handbags, and accessories. A truly special luxury feature not to be missed. The updated kitchen respects the integrity of the original architecture. Resort-style amenities include a private pool with two built-in grills, fitness room, and private tennis court, plus a four-car attached garage. Set in a remarkably private wooded setting in the Chappaqua Central School District, including Horace Greeley High School, with approximately 50-minute Metro-North access to Manhattan. A rare opportunity to own a significant work of architecture where privacy, nature, and extraordinary design converge.

20 Bessel Lane, Chappaqua
$1,995,000
4 Beds ⋅ 5 Baths ⋅ 1053697 MLS
Set in Chappaqua’s desirable Random Farms community with pool, tennis and sports court, this custom-built, sleek and sophisticated Contemporary offers a distinctive blend of architectural style, natural light, and comfortable living. An exceptional open floor plan features vaulted ceilings, skylights, custom windows, and a combination of wood and granite floors. The spacious eat-in chef's kitchen features custom Snaidero Italian white-lacquer cabinetry, granite countertops and flooring, top of the line stainless Subzero, Wolf induction and Bosch appliances, and abundant natural light. The adjoining family room with wood-burning fireplace opens seamlessly to the living and dining rooms, creating an ideal layout for both everyday living and entertaining. The second floor offers four generously sized bedrooms, including a private primary suite with marble bath, Jacuzzi tub, oversized shower, and walk-in closet. Additional bedrooms include ensuite and hall bath access. The finished walk-out lower level provides versatile additional living space for recreation, entertaining, or a home gym, with a full bath. Immaculately maintained and thoughtfully designed, this distinctive home within the highly coveted Chappaqua School District combines contemporary architecture with comfortable, functional living. Set on a beautiful, private property with level rear and side yards, this home also enjoys Random Farms’ amenities, including a pool, clubhouse, tennis courts, and sports court. Two-car attached garage with EV charging outlet, above ground Roth oil tank, and more. Not to be missed!

76 Random Farms Circle, Chappaqua
$2,349,000
5 Beds ⋅ 6 Baths ⋅ 1053148 MLS
Tucked into one of Chappaqua’s most coveted enclaves, this striking Random Farms Colonial is a standout 5-bedroom residence that lives like a 6-bedroom, with 4.5 baths and an effortless blend of architectural drama and resort-inspired luxury. Enter into a grand two-story foyer crowned by skylights and an elegant spiral chandelier, illuminating refinished hardwoods and leading to the heart of the home: a soaring two-story family room anchored by a warm wood-burning fireplace and walls of windows framing serene, golden sunset views. Designed for both grand entertaining and effortless daily life, the main level also features a formal living room with custom built-ins, an executive home office, convenient first-floor laundry, and a private guest suite complete with a full bath. The chef’s kitchen serves as a culinary showpiece with custom mitered cherry cabinetry, sleek dark granite countertops, a gathering center island, Sub-Zero refrigeration, Cafe double wall ovens, and a Bosch dishwasher—all opening seamlessly to an expansive wraparound deck. Upstairs, an open bridge walkway—suspended between and open to both the two-story foyer and family room below, creates an architectural centerpiece while naturally separating the sleeping wings. It leads to the secluded primary retreat, complete with a scenic balcony overlooking the grounds, his-and-hers walk-in closets, and an en-suite bath with a steam shower and soaking tub. Across the walkway, three additional bright bedrooms complete this level including an en-suite bedroom and two connected by a shared hall bath with all four upstairs bedrooms featuring custom built-in shelving. The fully finished walk-out lower level offers a self-contained multi-generational suite or the ultimate recreation destination, complete with a kitchenette, and abundant space for a home theater, gym, ping-pong, and pool table. Double doors spill out directly onto an expansive paver patio. Outdoors, the backyard is an exceptionally private haven framed by tiered stone retaining walls and mature woodlands. In addition to a large, flat lawn ideal for playing soccer and run freely, days are spent lounging on the wraparound deck or sun-drenched lower patio, and unwinding by the heated in-ground pool and integrated spa, protected by an automatic safety cover. Complete with a fully owned Tesla solar system, dual-unit central air, multi-zone heating, a double-wall above ground Roth oil tank, and a 240V Level 2 EV charging outlet in the garage plus Random Farms HOA clubhouse, pool, tennis, and sports courts. This home delivers an extraordinary lifestyle just minutes from top schools, town, and Metro-North.

48 Random Farms Circle, Chappaqua
$2,995,000
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 November 2026. Early buyers will have the rare chance to customize some 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

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.