Courtesy: Compass Greater NY, LLC
914-238-0676
Move right into this beautifully renovated 2-bedroom condo in Chappaqua’s sought-after Old Farm Lake community! Bright and airy with soaring ceilings, this home features a spacious, open living and dining area, an updated eat-in kitchen with high-end stainless steel appliances, and two generously sized upstairs bedrooms, each with its own renovated en-suite bathroom. Recent upgrades include brand-new Andersen windows and sliding doors throughout and fresh interior paint. An attached one-car garage with interior access adds everyday convenience. Perfectly situated just a stones-throw from the clubhouse, pool, tennis and sports courts, and playground, enjoy resort-style amenities right outside your door! Low taxes, easy condo living, and a prime location minutes from downtown Chappaqua, Metro-North, schools, Whole Foods, and Chappaqua Crossing complete the package. Turnkey living in an unbeatable location—just unpack and enjoy!
Courtesy: Houlihan Lawrence Inc.
914-238-4766
Welcome to 4 Hillside Place, an extensively updated townhome in the desirable Apple Hill Farm community! This recently renovated 3-bedroom, 3-bath home located on a quiet cul-de-sac road offers an abundance of space and natural light, complimented by a private outdoor patio and access to Apple Hill amenities. Enter to a convenient mudroom area leading to a sunlit, open-concept living room with a wood burning fireplace, custom built-ins, and crown molding. The renovated eat-in kitchen, with hardwood flooring and granite countertops, gives way to a private bluestone patio surrounded by trees and shrubs, with a beautifully appointed Lord and Burnham mini-greenhouse with a mahogany workbench. Upstairs, an airy primary bedroom features a Juliet balcony, walk-in closet, and ensuite full bath, while a second bedroom boasts plenty of storage with a walk-in closet and a second full bathroom. The newly-built third bedroom is bright and spacious with recently-installed skylights. A dedicated office nook with a new window completes the upper level. A one-car attached garage and driveway gives additional space. In its entirety, 4 Hillside Place has been lovingly and attentively updated. This townhome is the only unit in the community with an attached mini-greenhouse, which can be used for a potted kitchen garden or for additional storage. Outside your doors, the Apple Hill Farm neighborhood shines with 37 beautifully maintained acres featuring walking trails, a pond, a tennis court, and a heated in-ground pool. Close proximity to downtown Chappaqua, Metro North, the Chappaqua Library, plenty of restaurants, parks, and shops. This special home, with so many recent upgrades, is not to be missed!
Courtesy: Corcoran Legends Realty
914-332-6300
Beautifully Renovated Colonial with a Versatile Detached Studio on almost 1 and 1/2 Acres of Spectacular Park-Like Grounds. The renovations are extensive, including all-new Anderson windows, new electrical, new plumbing, a new roof, central air conditioning, a new Navien system, energy-efficient blown-in insulation, solid wide-plank oak flooring, and exquisite custom millwork throughout. Every detail reflects a thoughtful commitment to quality, comfort, and modern living. A true standout is the detached cottage-style studio, offering exceptional flexibility for today’s lifestyle. Completely updated with new electrical, windows, flooring, roof, and blown-in insulation, this versatile space is ideal for a private home office, artist’s studio, fitness or yoga retreat, creative workspace, or private retreat. The structure can also be converted back to a garage, providing even greater versatility. Inside the main residence, an original stone wood-burning fireplace anchors the living space with timeless charm. The chef’s kitchen features premium Thermador stainless-steel appliances, elegant quartz countertops, a spacious walk-in pantry, and direct access to an oversized slate patio—perfect for indoor-outdoor entertaining. The luxurious primary suite boasts soaring beamed ceilings, a generous walk-in closet, and a spa-inspired bath with dual vanities and a classic clawfoot soaking tub. Second-floor laundry with additional storage adds everyday convenience. Ideally located minutes from the Metro-North train station and downtown Chappaqua, this remarkable property combines extensive renovations, flexible bonus space, and a peaceful setting with convenient access to shopping, dining, and commuter routes.
Courtesy: EXP Realty
888-276-0630
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.
Courtesy: Compass Greater NY, LLC
914-238-0676
Location, Location, Location and the yard you have dreamt of! Set on a gorgeous, level, private acre on a flat cul-de-sac street that leads to sidewalks to downtown Chappaqua, Grafflin Elementary, and Bell Middle School, and just minutes from Whole Foods, Lifetime Fitness, Greeley High School, and more. This well maintained 3-bedroom, 2-bath home, with only $21,452 in taxes, shows pride of ownership the moment you walk down its blue stone walkway, with recent updates including a roof (2020), low-maintenance siding (2020), new AC (2020), new above-ground oil tank (2026), updated bathrooms, and a generator transfer switch for peace of mind. A well proportioned foyer opens to a spacious living room with wood-burning fireplace and large bay window, flowing seamlessly into a generously sized dining room. The sun-drenched eat-in kitchen with large picture windows and door opens to the oversized deck overlooking the picture-perfect backyard — providing ample space for outdoor dining and relaxing. Inside, are three well-appointed bedrooms, including a primary bedroom with recently renovated ensuite bathroom (2025) (hardwood under all bedroom carpets). The finished lower level boasts recessed lighting and second wood-burning fireplace with a door to the expansive backyard. The lower level also features built in shelves, and ample storage. The huge, flat backyard speaks for itself — perfect for all field sports, a playground, and trampoline (yes all three at once), home expansion, or - with septic in front - a possible pool site. Dream Big - Here!
Courtesy: William Raveis-New York LLC
914-401-9111
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.
Courtesy: Compass Greater NY, LLC
914-228-2656
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.
Courtesy: Howard Hanna Rand Realty
914-723-8700
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.
Courtesy: Houlihan Lawrence Inc.
914-238-4766
$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 Viking 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.
Courtesy: Houlihan Lawrence Inc.
914-238-4766
Welcome to Chestnut Oaks. Corner unit Townhome located in building 5 featuring 2 bedrooms, 2 full baths, fireplace, attached garage and balcony. Located in the heart of Chappaqua and close to train, town and schools. Renovated in 2010 with new dine-in kitchen, granite counter tops, stainless steel appliances, hardwood floors, renovated primary bathroom, custom walk-in closet, new washer/dryer and Bose speakers. Community outdoor pool and tennis.
Courtesy: Corcoran Legends Realty
914-332-6300
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.
Courtesy: Town and Village Real Estate
877-295-4111
NOW Easy to Show Welcome to this beautifully maintained raised ranch offering the perfect blend of space, comfort, and convenience in a highly desirable Chappaqua P.O. location within the award-winning Pleasantville School District. Situated on a quiet cul-de-sac, this 4-bedroom, 2-bath home features soaring cathedral ceilings, rich red oak hardwood floors, and an inviting open layout designed for both everyday living and entertaining. The spacious living room provides the ideal setting for gatherings and holidays, while multiple freshly stained multi-level decks create seamless indoor-outdoor living perfect for entertaining, summer barbecues, or relaxing evenings overlooking the expansive park-like property. The large yard offers endless possibilities for play, gardening, and recreation, plus three storage sheds for added convenience. Also included is a 11'x54' triangular shaped lot on north side of primary lot. .46 Acre Total Recent updates including a newer roof and boiler provide peace of mind, while the attached garage adds practicality and storage. Commuters will love the easy 5-minute walk to the Chappaqua train station with approximately 45-minute access to Grand Central Terminal. Rarely offered, this home also includes FREE school bus pickup within Pleasantville’s walking district. Ideally located just minutes from the farmers market, shops, restaurants, parks, and Metro-North, this move-in ready home delivers comfort, charm, and an exceptional lifestyle in one of Westchester’s most sought-after communities. Easy to show same day showings are ok now.
Courtesy: Houlihan Lawrence Inc.
914-238-4766
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.
Courtesy: Compass Greater NY, LLC
914-238-0676
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.
Chappaqua is located in New York. Chappaqua, New York has a population of 3,062. Chappaqua is more family-centric than the surrounding county with 35.47% of the households containing married families with children. The county average for households married with children is 35.32%.
The median household income in Chappaqua, New York is $196,141. The median household income for the surrounding county is $105,387 compared to the national median of $69,021. The median age of people living in Chappaqua is 44.3 years.
The average high temperature in July is 82.7 degrees, with an average low temperature in January of 20.6 degrees. The average rainfall is approximately 50.2 inches per year, with 32.5 inches of snow per year.
