Courtesy: Houlihan Lawrence Inc.
914-328-8400
Step into a home that blends space, light, and everyday convenience in all the right ways. This legal 3-bedroom residence lives like a 4-bedroom, offering flexible options including a potential first-floor bedroom—perfect for guests, work-from-home needs, or multigenerational living. At the heart of the home, a majestic family room with a fireplace creates a warm and inviting atmosphere, ideal for both relaxing nights and entertaining. Generously sized rooms are flooded with natural light, while beautifully refinished hardwood floors flow seamlessly throughout. The home features three full bathrooms, an oversized two-car garage with abundant storage, and a roof just 10 years young—providing peace of mind for years to come. Thoughtfully maintained and truly turn-key, this property is ready for its next chapter. Located directly across the street from Horace Greeley High School and Chappaqua Crossing, enjoy unmatched convenience with dining, shopping, grocers, health club, and more just moments away. A rare combination of space, flexibility, and prime location—this is the one you’ve been waiting for.
Courtesy: Julia B Fee Sothebys Int. Rlty
914-295-3500
A serene, light-filled retreat where modern design meets timeless comfort, this exceptional four bedroom four and one half bath contemporary residence offers an elevated lifestyle in one of Chappaqua’s most coveted settings. Set along a premier Chappaqua road on nearly three acres, the home is defined by its airy interiors, soaring ceilings, light hardwood floors throughout, and walls of windows that invite the outdoors in, framing tranquil, park-like views from nearly every vantage point. At the heart of the home, a beautifully renovated, oversized white Chef's kitchen with center island and sunlit breakfast area opens seamlessly to a dramatic family room with fireplace and multiple exposures. The main living spaces are gracious and interconnected, each oriented toward the lush, verdant grounds, offering a true indoor-outdoor lifestyle. A separate lower-level recreation or media room with direct access outside provides additional flexibility and ease. Sliding glass doors throughout lead to the yard creating an effortless flow for everyday living and elegant entertaining. The second level reveals a sophisticated primary suite with vaulted ceilings, custom built-ins, dual walk-in closets, and a spa-inspired bath. Additional bedrooms are generously scaled, complemented by a dedicated home office and versatile bonus spaces suited to today’s needs. A sweeping driveway and beautifully landscaped property enhance the home’s sense of privacy, while its location offers exceptional convenience—just moments to town, train, and top-rated schools. A rare offering that captures the essence of refined suburban living with all that Chappaqua has to offer.
Courtesy: Compass Greater NY, LLC
914-238-0676
Picture-perfect Colonial in one of Chappaqua’s most sought-after neighborhoods, blends timeless 1920s charm with modern comfort and style. Set on over an acre of exquisitely manicured, park-like grounds, this nearly 4,000 sq. ft. home offers 4 bedrooms, 2.5 baths, beautifully scaled rooms, and abundant natural light throughout. Anchoring the home, a magnificent living room welcomes you with a stunning stone fireplace—perfect for hosting friends or enjoying quiet evenings. Flowing seamlessly from the living room, the elegant dining room boasts two set of French doors leading to a patio and enclosed porch. Thoughtfully designed for everyday living, the eat-in kitchen connects to a family room filled with natural light from expansive windows. A spacious recreation room offers exceptional versatility, featuring two sets of French doors—one leading to a wisteria-covered deck and one to the gracious covered front porch. Completing the main level, a mudroom and powder room provide both convenience and functionality. Upstairs, the primary suite is a serene retreat with beamed ceilings, an en-suite bath, and an oversized walk-in closet, complemented by three additional generously sized bedrooms and a full hall bath. The picturesque property is a private oasis, featuring a fire pit, raised bed garden, tranquil pond and a stone patio with an outdoor kitchen—perfect for entertaining or relaxing in a peaceful, natural setting. Deer fencing and a privacy gate enhance the grounds and a full house generator ensure comfort at all times. A rare opportunity where architectural charm, expansive living spaces, an exceptional property, and a premier location come together for this truly special offering.
Courtesy: Compass Greater NY, LLC
914-238-0676
Bright and inviting, this 4-bedroom, 2.5-bath Colonial is ideally located with easy access to downtown Chappaqua, Metro-North, shops, dining, and local schools, offering the perfect balance of convenience and neighborhood charm. Thoughtfully designed for both everyday living and entertaining, the main level features a well-designed and functional layout with an open kitchen that flows seamlessly into the family room, creating a natural gathering space. A spacious living room with fireplace, formal dining room ideal for hosting, and a dedicated home office add flexibility for modern living. Upstairs are four well-proportioned bedrooms and two full baths, including the primary suite, providing ample space for guests. The finished lower level expands the home’s living area with excellent flexibility for recreation, fitness, play, or media. Outdoor living is just as inviting, with a screened porch overlooking the property, creating a wonderful setting for morning coffee, summer dinners, or relaxed entertaining. With generous living spaces, natural light throughout, and a thoughtful layout, this home offers effortless everyday living in a highly desirable Chappaqua location.
Courtesy: X-Cap Realty LLC
929-998-9227
This property is presented as a private and nature-oriented surrounded by wooded views and higher-end homes. The home features an open layout with large windows and modern updates, creating a bright, indoor-outdoor living experience suited for both relaxation and entertaining. Key highlights include updated finishes, a fireplace, and outdoor spaces like a deck/patio. Its location offers convenient access to downtown Chappaqua, transit, and major roads, making it appealing for commuters while still maintaining a peaceful suburban feel.
Courtesy: Compass Greater NY, LLC
914-238-0676
All the space and privacy of a single-family home with the ease of condo living! One of the few completely stand-alone and private townhouses in Apple Hill Farm, this spacious 2-bedroom, 2.5-bath home offers a rare blend of comfort, style, and convenience. Enjoy the serene setting from a large wrap-around wood deck overlooking lush, wooded views—perfect for morning coffee or evening entertaining. Inside, the sunny living room features a cozy wood-burning fireplace, oversized windows, and flows seamlessly into the formal dining area with sliding glass doors to the deck. The updated kitchen boasts custom cabinetry, brand-new stainless steel appliances, and its own access to the deck ideal for grilling or gatherings. All bathrooms have been newly and tastefully renovated with quartz vanities and striking tile flooring, bringing a luxurious feel throughout. Additional highlights include wood floors throughout, many new windows, a new roof and skylights (2019), and a new driveway and cul-de-sac (2019). Storage is plentiful with large closets, a pull-down attic, crawl space, and an attached garage. Apple Hill Farm is a private, tranquil community offering a pool and tennis courts, all just minutes from town, train, and top-rated Chappaqua schools. This move-in-ready home offers it all—privacy, space, and low-maintenance living in a coveted location.
Courtesy: Compass Greater NY, LLC
914-238-0676
A rare opportunity to own one of the few true 3-bedroom townhomes in Chappaqua Crossing Carriages, a sold-out luxury community within the highly sought-after Chappaqua School District. With all three bedrooms ideally situated on the second floor — a layout rarely available here — this exceptional end unit combines smart design with high-end finishes and extensive upgrades throughout. The main level offers a welcoming entry foyer with a versatile formal living room and powder room near the entrance, ideal as a sitting room, second office, or flex space. The heart of the home is the chef’s kitchen with custom cabinetry, premium appliances, waterfall quartz island, and pantry, open to the dining area and family room with gas fireplace. A two-car garage connects to a custom mudroom with built-in cubbies, bench, and closet. Upstairs includes three bedrooms, a dedicated home office, and a second family room with wet bar and wine refrigerator with large sliding glass doors to a large covered private terrace. The primary suite features a modern tray ceiling, a walk-in closet and spa-like bathroom with a double-sink vanity, oversized shower, and private toilet room. A hall bath with double sinks and a second-floor laundry room complete the level. Additional highlights include 12-foot ceilings, oversized windows, quartz countertops throughout, abundant storage, whole-house air filtration, and a full unfinished basement with plumbing and egress for future expansion. Community amenities include a clubhouse with gym, entertaining spaces, outdoor pool, shuttle to the Chappaqua train station, and walkable access to shopping, dining, Whole Foods and Life Time Fitness.
Courtesy: Julia B Fee Sothebys Int. Rlty
914-234-0200
1906 Grandeur. 2026 Luxury: The Ultimate Gated Sanctuary. Perched majestically atop a private hilltop, this gated 7,800-square-foot, five-bedroom estate presents a rare convergence of Gilded Age prestige and contemporary luxury. Believed to have been commissioned in 1906 for railroad magnate A.H. Smith, the residence has been masterfully renovated to honor its historic soul, featuring original interior stone walls and soaring ceilings that strike a perfect balance between grand scale and intimate warmth. Anchored by three distinctive hearths, the home is designed for both elegant living and everyday ease. A sun-drenched chef’s kitchen showcases a central island, dramatic overhead skylight, and professional-grade appliances. Unique architectural moments—including a circular-skylit Stargazer’s Nook—add character and charm, while the versatile five-bedroom layout offers both a magnificent two-story primary wing and a coveted first-floor private suite. Set on more than four exceptionally private acres, the grounds unfold as a true outdoor sanctuary, featuring a beautiful pool and spa (32x20), refined pergola terraces ideal for entertaining, and a private tennis court. From its commanding hilltop position, the estate delivers an unparalleled sense of privacy, security, and timeless elegance. Welcome home!
Courtesy: William Raveis-New York LLC
914-401-9111
Welcome to 2 DeWitt Drive — a stunning 2025-built carriage home offering refined luxury and effortless living in one of Chappaqua’s most desirable communities. This light-filled corner residence spans 3,574 square feet with 2 spacious bedrooms (with options for more) and 3.5 baths, thoughtfully designed with high-end finishes and sophisticated upgrades throughout. Expansive windows flood the home with natural light and showcase the beautiful grassy expanse bordering the front and side of the property, creating an airy, open feel rarely found in attached living. The main living spaces blend elegance and comfort with designer details, premium materials, and a seamless flow. The generous primary suite offers a true retreat, while flexible bonus spaces provide room for home office, media room, or guest accommodation. Enjoy warm-weather living on the expansive second-floor terrace with beautiful open views, or relax on the inviting front porch overlooking the generous grassy lawn right at your feet. This home delivers the best of new construction without the wait. Residents enjoy exclusive access to a private clubhouse featuring a beautifully appointed common area, fitness center, and pool. Located within the Chappaqua School District and set in a vibrant mixed-use community with Whole Foods, Starbucks, Restaurants and Shopping just moments away, this property offers a rare combination of luxury, convenience, and lifestyle. A sophisticated, low-maintenance opportunity in the heart of Chappaqua.
Courtesy: Compass Greater NY, LLC
914-238-0676
Beautifully appointed and meticulously maintained 4 bedroom, 4 1/2 bath Colonial set on a level acre at the end of a quiet cul-de-sac in prestigious Inglenook Farm in the coveted Byram Hills Schools. A grand and light-filled two-story entry welcomes you into this refined open layout home featuring 9-foot ceilings on 1st and 2nd levels, oak flooring, and custom moldings and trim throughout. Formal living and dining rooms lead to a Chef's eat-in kitchen with granite countertops, oversized island, stainless appliances and dining area. The kitchen opens to a spacious family room with wood burning fireplace and doors to an expansive deck overlooking the serene, park-like level backyard. A mudroom off the kitchen provides everyday convenience, and a separate back bonus/recreation room adds flexible space for work, play, or relaxation. Upstairs, the primary suite features a spa-like bath, dressing area, and oversized custom-outfitted closet. The finished legal walkout lower level includes a large recreation room, gym, full bath, and ample storage. Other highlights include a large laundry room, large walk-in pantry and a 3-car attached garage. Whole house generator. Located just minutes to the towns of Chappaqua and Armonk, in the Byram Hills School District and just 45 minutes from NYC, this home is not to be missed.
Courtesy: Compass Greater NY, LLC
914-238-0676
Welcome to this move-in-ready 2-bedroom, 2-bath residence in highly sought-after Chappaqua Commons. Recently refreshed with thoughtful updates throughout, this sun-filled home combines modern finishes with effortless convenience. The spacious open-concept living and dining area features brand-new flooring (2025) and a seamless flow to the updated kitchen, boasting new countertops and backsplash (2025)—perfect for both everyday living and entertaining. Two generously sized bedrooms include a primary suite with a newly updated bath, while the second bath has also been beautifully renovated and has laundry. Enjoy the ease of one-level living, ample closet space, and a location that can’t be beat—just seconds to downtown Chappaqua’s shops, restaurants, Metro-North train, and parks. Move right in and start living your best Chappaqua lifestyle!
Courtesy: Houlihan Lawrence Inc.
914-723-8877
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.
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.
