Chappaqua, NY Homes for Sale: Your Guide to Exceptional Westchester Living

Advanced Search Market Reports Home Value Connect

Discover an exquisite selection of homes for sale in Chappaqua, NY, a highly sought-after hamlet in Westchester County known for its prestigious schools, picturesque landscapes, and vibrant community. Tierra Stanback presents a diverse portfolio ranging from charming historic residences to modern luxury estates, catering to discerning buyers seeking a tranquil yet connected lifestyle. Explore available properties, understand local market trends, and find your ideal Chappaqua home, whether you desire a spacious family abode near top-rated schools or a secluded retreat amidst nature's beauty. Chappaqua's unique blend of suburban tranquility and convenient access to NYC makes it a premier destination for those seeking exceptional living.

Search Chappaqua, NY by Lifestyle

Search Chappaqua, NY by Price

Search Chappaqua, NY by Bedrooms

Search Chappaqua, NY by Bathrooms

Exploring Chappaqua's Diverse Real Estate Market

The array of homes for sale in Chappaqua, NY, presents an incredible opportunity for discerning buyers seeking a blend of sophistication and suburban comfort. This picturesque hamlet, nestled within New Castle in Westchester County, boasts a dynamic real estate landscape.

Luxury Homes and Estates in Chappaqua

For those seeking unparalleled elegance, Chappaqua offers a remarkable selection of luxury homes and expansive estates. These properties often feature sprawling acreage, custom architectural designs, and high-end amenities, providing privacy and opulence. Many luxury listings showcase gourmet kitchens, home theaters, and private pools, reflecting the affluent lifestyle synonymous with this area.

Family-Friendly Homes Near Top Chappaqua Schools

A significant draw for families exploring homes for sale in Chappaqua is the highly-regarded Chappaqua Central School District, including the prestigious Horace Greeley High School. Buyers frequently seek single-family homes situated in close proximity to schools, offering convenience and a strong sense of community. These properties often feature spacious yards, multiple bedrooms, and family-oriented layouts, ideal for raising children.

Historic Charm and Modern Residences

Beyond contemporary luxury, the Chappaqua real estate market also includes charming historic homes, many meticulously maintained and updated. These residences often tell a story, featuring unique architectural details from bygone eras. Conversely, new construction homes are also available, offering modern design, energy efficiency, and the latest smart home technology to suit contemporary tastes.

Chappaqua Neighborhoods: Finding Your Perfect Place

Understanding Chappaqua's distinct neighborhoods is key when searching for the ideal home. Each area offers a unique ambiance and property style.

Whippoorwill: Secluded Estates and Privacy

The Whippoorwill section is renowned for its larger properties and a heightened sense of seclusion. Here, residents find magnificent estates set on generous parcels of land, often bordered by natural woodlands. These homes for sale appeal to those prioritizing privacy and expansive outdoor living.

Quaker Street Area: Classic Homes and Community Feel

The Quaker Street area is cherished for its classic Chappaqua homes, often Colonials or Victorians, situated on well-manicured lots. This neighborhood fosters a strong community feel, with many properties offering easy access to the town center and local amenities.

Lawrence Farms East: Prestigious Living

Lawrence Farms East is another highly sought-after enclave, characterized by its prestigious homes and well-established streetscapes. Properties here represent a blend of classic architecture and modern upgrades, appealing to buyers looking for elegance and a prime location.

The Chappaqua Lifestyle: More Than Just a Home

Living in Chappaqua extends beyond the four walls of your home; it's about embracing a superior quality of life.

Exceptional Education: Horace Greeley High School and Beyond

The Chappaqua Central School District consistently ranks among the top in New York State. This commitment to educational excellence is a primary driver for many families looking at homes for sale in Chappaqua, ensuring access to outstanding public schools from elementary through high school.

Outdoor Recreation and Green Spaces

Nature enthusiasts will appreciate Chappaqua's abundance of parks and green spaces. Gedney Park offers walking trails and recreational facilities, while the nearby Rockefeller State Park Preserve provides miles of picturesque trails for hiking, horseback riding, and enjoying the tranquility of nature. Finding a home for sale close to these amenities enhances the Chappaqua living experience.

Commuting from Chappaqua: Convenience to NYC

Chappaqua's strategic location in Westchester County provides convenient access to New York City. The Chappaqua Metro-North station offers frequent express service to Grand Central Terminal, making it an ideal location for commuters seeking a peaceful suburban retreat without sacrificing urban accessibility. Many homes for sale are attractive due to their proximity to the train station.

Navigating the Chappaqua Real Estate Market with Tierra Stanback

Identifying the perfect home among the many desirable homes for sale in Chappaqua, NY, requires local expertise. Tierra Stanback is dedicated to providing comprehensive guidance, helping buyers understand market nuances, explore off-market opportunities, and navigate the purchasing process with confidence. Whether you are searching for a starter home, a sprawling estate, or an investment property, Chappaqua offers diverse options waiting to be discovered.

Newest Homes for Sale in Chappaqua, NY

$825,000

3 Beds ⋅ 3 Baths ⋅ 1062795 MLS

Welcome to Apple Hill Farm, a beautifully landscaped community set on over 37 wooded acres. Nestled on a quiet cul-de-sac, this sun-filled, renovated 3-bedroom, 2.5-bath end-unit townhome offers privacy, comfort, and modern living. The open-concept layout features soaring ceilings, Andersen windows, skylights, custom built-ins, and a wood-burning fireplace. The modern eat-in kitchen boasts white cabinetry, quartz countertops, stainless steel appliances, and a breakfast bar. Sliding doors from the kitchen and dining area open to a spacious private deck and yard. Extensive updates since 2025 include renovated bathrooms, new laminate flooring in the living and dining areas, new tile flooring in the kitchen, laundry room, and powder room, new pine hardwood floors on the upper levels, refinished staircases, fresh paint throughout, an updated laundry room with new washer and dryer, and newly replaced and stained deck flooring. The primary suite features a Juliet balcony, en-suite bath with double vanity, and generous closets. Additional highlights include central air, abundant storage, and a heated attached garage. Enjoy the community pool and tennis courts, conveniently located near downtown Chappaqua, Metro-North, shops, restaurants, and schools. A wonderful combination of privacy, modern updates, and convenience!

2 Timberland Pass, Chappaqua

$2,799,000

6 Beds ⋅ 5 Baths ⋅ 923774 MLS

Distinguished and timeless, this exquisite pre-war Colonial is beautifully renovated and meticulously maintained, privately set amid mature specimen trees and spectacular, level, park-like grounds at the end of a gorgeous, quiet, estate-studded cul-de-sac in Lawrence Farms East, one of the area's most sought-after neighborhoods. A rare blend of classic architectural elegance, gracious living spaces, and modern amenities, this exceptional home offers extraordinary privacy and a serene natural setting. Rich in character and craftsmanship, the home features intricate hardwood floors, elegant moldings, fine millwork, and French doors throughout. The expansive and inviting front-to-back Living Room, with its wood-burning fireplace, opens to a screened porch overlooking the stunning grounds. A gracious Dining Room, also with door to the screened porch, adjoins the beautifully updated eat-in Kitchen, appointed with high-end appliances, marble countertops and center island, and a wall of glass-front cabinetry, creating an elegant and functional space for everyday living and entertaining.The dramatic, wood beamed Family Room is a true highlight, with a fireplace and door to the patio. A first floor office/study, with ensuite bath, laundry room, mudroom and renovated powder room complete the first floor. On the second floor, the light-filled primary suite offers a door to a balcony and renovated en-suite bath with radiant heat and steam shower, is complemented by four additional generously proportioned bedrooms. Two renovated full baths and a gym/office complete the second floor. With lots of multi-use rooms, this home offers exceptional flexibility for guests, home offices, and additional living needs. Set on approximately two acres of level, park-like property, the grounds feature expansive lawns with abundant room for play, recreation, and relaxation, complemented by an inviting fire pit, elegant stone walls, and a welcoming patio— all framed by mature trees and lush natural surroundings. The remarkable setting combines the beauty of a private estate with the convenience of a coveted neighborhood location. Substantial recent upgrades include a new roof (2025), new boiler (2025), ductless split air-conditioning systems (2024) and generator. Natural gas utilities, a detached two-story garage with exceptional bonus storage space above, and an EV car charger add further convenience. Enjoy an enviable location within walking distance of Horace Greeley High School, Mount Kisco Country Club, the renowned Crabtree's Kittle House, and Chappaqua Crossing, featuring Whole Foods, Life Time Fitness, the Chappaqua Performing Arts Center, and an array of additional shopping and dining options. A truly exceptional offering that combines distinguished Colonial architecture, sophisticated updates, generous living spaces, and magnificent private grounds in one of Lawrence Farms East's most desirable settings.

18 Ivy Hill Road, Chappaqua

$3,995,000

5 Beds ⋅ 6 Baths ⋅ 1031593 MLS

A long, majestic, illuminated tree-lined driveway introduces this sophisticated Colonial , privately nestled on one of Chappaqua most prestigious cul-de-sac streets. Surrounded by professionally landscaped grounds, mature specimen trees, and lush greenery, this exquisitely renovated and impeccably maintained residence offers over 7,000 square feet of extraordinary living space, unparalleled privacy, and timeless elegance . New hardwood floors, detailed millwork , marble and travertine radiant heated floors, custom built ins , architectural moldings, and modern renovated bathrooms showcase outstanding craftsmanship and attention to detail. A soaring two-story foyer, sweeping staircase with custom designed banister, and floor to ceiling windows create an impressive entrance. The formal living room with fireplace and elegant dining room flank the foyer. The light-filled, open floor plan centers around a spectacular double-height family/great room featuring custom picture windows, a wood burning fireplace, and French doors to an expansive patio overlooking the orchard-like grounds. The adjoining eat-in kitchen offers an oversized island and sunlit breakfast area. A four season room with walls of windows and an adjacent office with a striking marble fireplace provide additional exceptional spaces. Two renovated powder rooms , a laundry room , and a spacious mudroom with side porch access and a three-car heated garage complete the first floor. The second floor features a luxurious primary suite with an oversized and vaulted ceiling bathroom, expansive walk-in closet, and two additional closets, plus four generously sized bedrooms, two with exquisitely renovated en-suite baths and a second family room. The finished lower level includes a large recreation room, home gym, full bathroom, and enormous storage. Outside, custom designed landscaping and property lighting, sweeping lawns, specimen trees , and flowering gardens create a private oasis, complemented by expansive bluestone terraces, a fire pit and a generous patio ideal for entertaining and outdoor enjoyment. Significant improvements include a driveway, Azec trim, freshly painted exterior, roof , comprehensive drainage system , stone retaining walls, boiler and condensers . Ideally located minutes from Chappaqua town, the train, and major highways, and less than an hour commute from Manhattan this exceptional property is situated within the award-winning Chappaqua Central School District . A truly rare offering combining refined living, remarkable space, and extraordinary privacy in a premier location. For the discerning buyer.

9 Trails End, Chappaqua

$3,088,000

7 Beds ⋅ 7 Baths ⋅ 1055737 MLS

Welcome to The Roaring Brook Estate, a rare Chappaqua retreat set on more than seven private acres of natural beauty, architectural significance, and quiet history. Just about one hour north of Manhattan, this distinctive property offers a remarkable combination of privacy, land, design, and lifestyle. Originally built in 1958, the residence is known in architectural records as the Donald Miller Jr. House, Now the Roaring Brook Estate, and was designed by celebrated American modernist architect Edward Larrabee Barnes. The home was featured in Architectural Record Houses of 1959, with USModernist identifying the original project team as including structural engineer William Atlas, builder O’Brien and Kinkle, landscape designers Bye and Herrmann, and interiors by Mary Barnes and Emily Malino. The architecture reflects Barnes’s modernist philosophy: clean lines, openness, natural light, and a close relationship between the residence and the surrounding landscape. Glass, structure, and proportion work together to frame the outdoors rather than compete with it, creating a home that feels deeply connected to its setting. Surrounded by mature trees, open lawns, a peaceful brook, and beautiful natural scenery, the estate creates an immediate sense of calm and escape. The property unfolds through light, landscape, and privacy — morning sun through the trees, quiet afternoons across the grounds, and peaceful evenings surrounded by nature. Here, the land is not simply a backdrop; it is part of the living experience. In addition to the main residence, the property also includes a separate guest house featuring a beautiful studio space, currently occupied by a tenant. This added structure enhances the estate’s flexibility and creates potential for guest accommodations, creative use, private work space, or income-producing use, subject to applicable lease terms and local requirements. This is a unique opportunity for the next owner to enjoy, restore, or reimagine a significant modernist estate with character, history, and long-term lifestyle potential. Whether used as a full-time residence, weekend retreat, creative sanctuary, or private gathering place, 301 Roaring Brook Road offers the space, privacy, and atmosphere that are increasingly difficult to find in Westchester. Located in desirable Chappaqua, the property is close to village conveniences, Metro-North, parks, trails, and the highly regarded Chappaqua school district. More than a home, The Roaring Brook Estate is a setting, a story, and a rare opportunity to become the next steward of one of Chappaqua’s most memorable properties.

301 Roaring Brook Road, Chappaqua

$2,790,000

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

$1,599,000

8 Beds ⋅ 8 Baths ⋅ 1052500 MLS

There are houses you pass without a second thought, and then there are houses you remember. For years, set quietly behind a canopy of mature trees along Bedford Road, this stately white Georgian has inspired curiosity. What is behind those walls? What could it become? Now, offered for the first time in decades, the doors to 600 Bedford Road are opening and with them comes a remarkable opportunity to write the next chapter of a truly special Chappaqua property. Ideally positioned between Chappaqua and Mount Kisco, this substantial residence encompasses just shy of 6,000 square feet with 8+ bedrooms and 6+ baths. Grand in scale yet filled with character, the home offers an extraordinary amount of space and flexibility for living, entertaining, working, and hosting Its balanced Georgian facade, impressive proportions, and timeless architectural presence speak to another era. Local history has long associated the property with the greater Lawrence Farms estate, adding another layer of intrigue to a home that already feels as though it has a story to tell. Inside, the expansive layout unfolds room after room, offering a rare canvas for someone with vision. This is not a house that asks to become something ordinary. Thoughtfully restore its classic character, reimagine it for modern living, or create a home that blends the best of both. With this much space, presence and possibility, the opportunities are endless. And then there is the location. Tucked behind its blanket of trees, 600 Bedford Road feels wonderfully removed, yet Chappaqua and Mount Kisco are both just minutes away. Metro North, shopping, dining, recreation and the conveniences of both villages are within easy reach, all within the Chappaqua Central School District. Homes of this scale and character are increasingly difficult to find. For decades, 600 Bedford Road has quietly waited and now it's time for it's next chapter to begin.

600 Bedford Road, Chappaqua

$2,299,000

5 Beds ⋅ 5 Baths ⋅ 1036792 MLS

Welcome to 20 Hitching Post Lane in Chappaqua, New York. This five-bedroom, 4.1 bath Colonial is set on over 2 bucolic acres on a beautiful tree-lined street. An impressive oak floored entry foyer with cherry inlay opens to a spacious formal living room with crown moldings and new windows (2023), warmed by a wood burning fireplace with decorative mantle. The adjacent family room has a second wood burning fireplace, this one brick, spanning floor-to-ceiling with raised hearth. Sliding glass doors lead from the Family Room to an Azek deck installed in 2016. Walk through the formal dining room accented with chair rail and crown molding, into a chef's kitchen with Richmaid cabinetry and tumbled marble backsplash with hand painted accents, a center island, and GE Monogram 6 burner gas stove with convection oven, farm sink, GE Monogram side/side refrigerator, microwave and dishwasher. Sliding glass doors open from the kitchen to deck with internal shades. The second floor Primary bedroom has a private bath with steam shower, double vanity and a Crema Marfil counter, whirlpool tub and radiant heated stone floors. The walk out lower level is included in the square footage and has a laundry room, playroom and a full bath. The mechanicals include: 4 zone heat, 3 zone AC, sophisticated sound system and CAT 5 wiring, full house generator (2014) Azek deck with an automated awning, fenced in yard, above ground oil tank (2024) and irrigation system. Enjoy this professionally landscaped retreat, minutes from downtown with easy Metro-North railroad service to New York City.

20 Hitching Post Lane, Chappaqua

$5,750,000

6 Beds ⋅ 8 Baths ⋅ 1017994 MLS

Welcome to 24 Trails End, an unparalleled private resort estate redefining luxury living on over 9 pristine, park-like acres. This majestic brick Colonial, quietly positioned at the end of a prestigious cul-de-sac, overlooks a scenic, spring-fed pond. Inside, classic architectural sophistication meets modern design, highlighted by a soaring double-height great room, dual home offices, and a rich mahogany billiard room with a wet bar and fireplace. The heart of the home is an expansive chef's kitchen, with an oversized marble island, and a sunny breakfast area. The lower level is an extraordinary recreation destination, boasting a 2600 sqft indoor sports court lined for basketball and pickleball, alongside a full home gym. Step outside to your private backyard paradise with an inviting heated Gunite pool, integrated spa, and a pool house/cabana surrounded by sprawling bluestone terraces and meandering walking trails. Two firepits located around the property and a serene pond with an island, an additional firepit and two docks for unmotorized boat usage complete this spectacular picture. An ultra-private lifestyle compound in the award winning Chappaqua schools, just under an hour from Manhattan.

24 Trails End, Chappaqua

$1,780,000

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

$1,665,000

1038452 MLS

Extremely rare and ultra-private 12.92 acres of waterfront land in the Whippoorwill Lake enclave of Chappaqua. An exceptionally private canvas for a one-of-a-kind secluded getaway compound. Beyond the gate, a long private drive ascends to a concealed building site with sweeping lake and woodland vistas, plus natural water features including a waterfall and bridge. Near Whippoorwill Park, Chappaqua’s largest preserve (169 acres) and adjoining other protected woodlands. Minutes to Chappaqua, Armonk, and Mt. Kisco, express NYC commute and just 15 minutes to Westchester County Airport. Choice of Chappaqua or Armonk schools. The land sits within the Croton Watershed. An optional, stunning modern architectural package designed specifically for the site to maximize bucolic views. Full plan set and renderings available under separate agreement ($250,000). A truly one-of-a-kind and rare offering. Showings by appointment only for discerning, qualified buyers with verified proof of funds. Ideal for those seeking to build a custom private compound or a bespoke retreat.

767 King Street, Chappaqua

$1,490,000

3 Beds ⋅ 4 Baths ⋅ 1017997 MLS

$100,000 REDUCTION 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

$1,495,000

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

Start Your Search

Prev
1
2
of 2
Next

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.