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Chappaqua, New York Homes for Sale

There is something for everyone in the town of New Castle and the hamlets of Chappaqua and Millwood. New Castle has many beautiful parks, including Gedney Park that was voted best in Westchester in 2008.

In Chappaqua there is always something you can find to do! Wake up and roll into a chair at Le Jardin du Roi, to taste 2005 Westchester Magazine's "Best Breakfast." You can also head up the hill for a great sandwich at Lange's Little Store and Delicatessen (382 King St.). The Crown House Antiques is a great place for a little antique shopping. It's a great place to shop and savor the history of its objects. At the old Millwood Train station you can take a mental trip back in time to when the town grew up around it.

The town also has lots of history. The New Castle Historical Society's Headquarters in the Greeley House is where you can learn about the fascinating history of Chappaqua, including figures like Horace Greeley and religious groups like the Quakers.

When the railroad came to Chappaqua in 1848, the farms began to grow and ship "cash crops." To package and ship the cider, vinegar, apples, milk and other products, residents built cider mills, a pickle factory and a barrel factory. The two hamlets of Chappaqua and Millwood developed freight stations, livery stables, general stores and hotels. Later, 19th century industries included the Spencer Optical Works, near Mount Kisco, and the Bischoff Shoe Company in Chappaqua. Nevertheless, the Town remained a very small town, with 1,800 people in 1850 and less than 2,500 at the end of the century. Gradually, the local industries lost their vitality, but the beauty of the land and the relative ease of transportation provided by the railroad remained and began to attract people who had accumulated wealth in New York City. Among these was Horace Greeley, who first bought land in Chappaqua in 1853 and began assembling his 78-acre farm. It occupied much of what is now central Chappaqua, including the Horace Greeley House, the Robert E. Bell Middle School, the Church of Saint Mary the Virgin, the Chappaqua Library, and the Chappaqua railroad station. Greeley was America's foremost newspaper editor, and an unsuccessful Presidential candidate, losing to Grant in 1872 and died within a month of the election.

Following the World Wars, population of the town grew greatly. In the 1920's realtors promoted "the high pure air belt of Chappaqua." The Saw Mill River Parkway reached the Town in 1934 and in the late 30s and 40s lasting real estate developments took root. The most dramatic population increase came in the years following World War II. From 1950 to 1960 the number of people in New Castle rose by 60% to more than 14,000. A major factor in this increase was the acknowledged excellence of the Chappaqua school system.

The town also has lots of history. The New Castle Historical Society's Headquarters in the Greeley House is where you can learn about the fascinating history of Chappaqua, including figures like Horace Greeley and religious groups like the Quakers. Take one of their worthwhile walking tours around Chappaqua or take one of your own. When the railroad came to Chappaqua in 1848, the farms began to grow and ship "cash crops." To package and ship the cider, vinegar, apples, milk and other products, residents built cider mills, a pickle factory and a barrel factory. The two hamlets of Chappaqua and Millwood developed freight stations, livery stables, general stores and hotels. Later, 19th century industries included the Spencer Optical Works, near Mount Kisco, and the Bischoff Shoe Company in Chappaqua. Nevertheless, the Town remained a very small town, with 1,800 people in 1850 and less than 2,500 at the end of the century. Gradually, the local industries lost their vitality, but the beauty of the land and the relative ease of transportation provided by the railroad remained and began to attract people who had accumulated wealth in New York City. Among these was Horace Greeley, who first bought land in Chappaqua in 1853 and began assembling his 78-acre farm. It occupied much of what is now central Chappaqua, including the Horace Greeley House, the Robert E. Bell Middle School, the Church of Saint Mary the Virgin, the Chappaqua Library, and the Chappaqua railroad station.

Following the World Wars, population of the town grew greatly. In the 1920's realtors promoted "the high pure air belt of Chappaqua." The Saw Mill River Parkway reached the Town in 1934 and in the late 30s and 40s lasting real estate developments took root. The most dramatic population increase came in the years following World War II. From 1950 to 1960 the number of people in New Castle rose by 60% to more than 14,000. A major factor in this increase was the acknowledged excellence of the Chappaqua school system.

The mission of the Chappaqua Schools is to create a community for learning, where students, parents and staff are joined in the pursuit of academic excellence and personal growth in a caring environment. We seek to develop each student's full potential through a challenging curriculum, a diversified faculty, and a commitment to intellectual freedom. We will teach basic skills, foster creative and critical thinking, and provide a foundation for life-long learning. We will nourish our students' emotional lives and guide their social development, instilling in them an appreciation of self-worth, of individual difference, and of global interdependence. We will help them learn how to manage freedom and to act ethically so that each may become a responsible, contributing member of society. 

Town of New Castle: http://www.mynewcastle.org/
Chappaqua Central School District: http://www.chappaqua.k12.ny.us/index.cfm

Chappaqua Homes for Sale

$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

$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

$1,800,000
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

$1,594,000
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

$1,590,000
3 Beds 3 Baths 1017997 MLS
Tastefully Expanded and Renovated Colonial in the Heart of Chappaqua - New 4 bedroom Septic, 2024 Roof and Exceptional Indoor/Outdoor Living. Just moments to Chappaqua village, Metro North and highly regarded Chappaqua schools. A flexible first-floor guest/au pair suite with private bath, chefs kitchen with Wolf appliances, private primary suite, 2 fireplaces, expansive deck and mature grounds backing to protected green space. 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, a coffered ceiling, 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 au pair/guest room and full bath. 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

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