Courtesy: Houlihan Lawrence Inc.
914-238-4766
Nestled on a quiet cul-de-sac, 2 Apple Tree Close is a rare 1930s Colonial that beautifully honors its architectural heritage while offering the comforts of contemporary living. Located within the award-winning Chappaqua Central School District, this 3-bedroom, 1.5-bath residence perfectly preserves both authenticity and timeless appeal. Behind the original front door, a welcoming entry and closet lead to two flexible living spaces anchored by an original wood-burning fireplace. Preserved millwork and beautifully maintained lime wash walls run throughout the home, enhancing its distinct character. Adjacent to the living room, a generous dining room featuring stained glass millwork and leaded glass doors opening into the kitchen, complete with stainless steel appliances, terracotta tile floors, a charming breakfast nook, and convenient half bath. Upstairs, the primary bedroom boasts large windows, a cozy sitting area, and double closets. The connected primary bath features a spacious walk-in shower and provides access to two additional bedrooms, each with ample closet space. Set on a half-acre of flat, usable park-like land, the fully fenced backyard offers privacy and abundant space to gather, garden, or unwind. Additional features include a flagstone patio, two-car garage and a full-house generator, providing ease and peace of mind year-round. Just moments from Chappaqua Crossings and the Metro-North train station, this charming home offers the rare opportunity to own a true Chappaqua classic in an outstanding 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: Compass Greater NY, LLC
914-238-0676
Meticulously maintained and move-in ready, this light-filled 4-bedroom, 2.5-bath contemporary is set on one of Chappaqua’s most desirable streets. The open-concept layout offers seamless flow for everyday living and entertaining, enhanced by exceptional natural light throughout provided by pristine windows. Updated baths in 2025 bring a fresh, modern feel, complementing the home’s clean architectural lines. The property backs to 11 acres of preserved land, creating rare privacy and peaceful views without the upkeep. Connected to municipal sewer for added convenience and long-term value. An unfinished basement with over 500 square feet offers abundant storage and exciting potential for future finished space. Ideally located just minutes to Grafflin Elementary, Downtown Chappaqua, and Metro-North, this home offers the perfect balance of privacy and accessibility. Turnkey, well-located, and filled with opportunity.
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: William Raveis-New York, LLC
914-238-0505
Dreamy modern ranch nestled on a private landscaped acre on a cul-de-sac in sought-after Whippoorwill. A flagstone walkway leads to a covered entry. The contemporary-styled front door with cross-reed glass panels and sidelight sets a refined first impression. Designed for effortless indoor/outdoor living, the rear-facing living room anchors the home with a wood-burning fireplace and two sets of French doors opening to a wrap-around Trex deck. Designer Runtal vertical panel hydronic radiators add comfort and style to the space. The sleek kitchen is outfitted with electric Thermador double wall ovens, a built-in Thermador microwave, Jenn-Air cooktop, panel-finished Sub-Zero refrigerator and freezer, Bosch dishwasher, custom cabinetry with under-cabinet lighting, narrow glass subway tile backsplash, and granite countertops. A dining area adjoins the kitchen and living room. A private corner office with built-ins enjoys sweeping views from walls of windows and a French door to the deck. Private quarters are composed of four comfortably sized bedrooms, including a primary with ensuite bath and a hall bath with shower over bathtub. The finished walk-out lower level delivers a generous family room with custom built-ins and a sliding glass door to a covered patio; a large, finished laundry room with built-ins, sink and space for arts and crafts; a powder room plus access to the oversized two car garage. Natural gas fuels the heat, hot water and the Generac 22kW automatic backup generator. Finishing touches include blown-in insulation, modern metal cable railing surrounding the deck, and a Trex RainEscape system underneath to keep the covered patio dry. Nice sized lawns for play or relaxation front and rear with a fenced rear yard. Mature and established landscaping highlighted with andromeda, holly, blue spruce, and arbor vitae. Near Horace Greeley High School, the shops and amusements at Chappaqua Crossing, the Town of New Castle’s Whippoorwill Park, and the noted, private Whippoorwill Club.
Courtesy: Houlihan Lawrence Inc.
914-328-8400
Experience the art of living well in this extraordinary private retreat overlooking Heaptaugua Lake. Set on just under five acres, the property offers total serenity while remaining just minutes from Chappaqua’s quaint downtown, restaurants, Metro-North, and shopping. Enter through the gates and follow the sweeping driveway as it curves past the pool house and pool, passing a sweeping lawn before reaching the main residence. This sophisticated one-level contemporary is deceptively understated from the front yet opens dramatically in the rear with walls of glass and lofted ceilings framing breathtaking views of mature trees and shimmering water. Multiple living spaces flow effortlessly to expansive terraces, anchored by a striking double-sided stone fireplace serving both the living and dining rooms. The private bedroom wing includes three bedrooms, highlighted by a serene primary suite with a stunning spa-like bath, while a separate fourth bedroom and family room on the opposite side of the home create the perfect guest quarters. An art lover's dream with gallery style hallways perfect for showcasing a collector's treasured works. A chef’s kitchen completes the offering with custom Italian cabinets by Schiffini, creating an intimate space for meals yet perfect for entertaining. Rarely does a property of this caliber and setting become available—an exceptional opportunity awaits.
Courtesy: Compass Greater NY, LLC
914-238-0676
Immaculate townhouse in a desirable walk-to-town location close to shops, restaurants, and the train. Refinished maple hardwood floors, custom built-ins, and a fireplace define the main living level, highlighted by a dramatic wall of windows with sunset views. Newer Pella sliders open to a private deck for seamless indoor-outdoor living. Custom stair railings, upgraded solid interior doors, and designer shades elevate the home throughout.The updated kitchen features Bilotta cabinetry, GE Profile appliances, and quartz countertops, complemented by tastefully renovated baths. The primary suite offers custom closets, an en-suite bath, and sliders to a private deck, while the second bedroom also includes an en-suite bath. Vaulted ceilings enhance light and volume. This unit includes 2 assigned parking spaces as well. Recent improvements include windows replaced in 2025, a new furnace in 2024, an AC unit replaced in 2025, and a new hot water heater, offering move-in-ready peace of mind.
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. 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: Houlihan Lawrence Inc.
914-238-4766
Updated end-unit townhome with an oversized patio, featuring 3 bedrooms, 2.1 baths, and a spacious loft in the sought-after Apple Hill Farm complex. Airy and private. Tranquil setting among apple orchards and woody walking trails by the pond. This beautiful unit has been extensively renovated and offers hardwood floors throughout, fresh paint, an updated kitchen with stainless steel appliances and granite countertops, and updated baths with quartz vanities. The dramatic living room features a fireplace, double-height ceiling, and oversized windows, and opens seamlessly to the dining area with sliding glass doors leading to the oversized patio. Additional upgrades include several brand-new windows and skylights. The home also features a spacious loft, in-unit laundry, an attached one-car garage, French drainage, and an open floor plan. The complex offers a community pool and tennis courts. Conveniently located minutes from town, Chappaqua schools, and the Chappaqua train station. Not to be missed—this home will not last!
Courtesy: Houlihan Lawrence Inc.
914-238-4766
Custom design your dream home in a seamless process with ZappiCo, Westchester County's premier Real Estate Developer! This luxurious home is to-be-built in the highly desirable Chappaqua school district. With 4 spacious bedrooms and 2.5 beautifully appointed bathrooms, this home will be meticulously crafted with the finest materials and attention to detail. As you enter, you will be greeted by an open concept living and dining area, perfect for entertaining guests or relaxing with loved ones. The gourmet kitchen will feature an open layout with quartz countertops and semi-custom cabinetry. The open concept main level will also offer a family room & living room - perfect for those who work from home or need a quiet space to study. Upstairs, you will find a spacious primary suite complete with a spa-like en suite bathroom and walk-in closet, as well as three additional bedrooms with ample closet space. Other features of this home will include hardwood flooring throughout, energy efficient windows, 2-zone central air, and a full finished basement (1,000 sf. incl. in total sf) ready for your personal touch. Outside, landscaping is included to create your own oasis. Located just a short distance from local restaurants, shops, and parks, this home offers the perfect blend of luxury living and convenience. With the ability to customize your finishes and personal touches, this to-be-built home is the perfect opportunity to create your dream home in Chappaqua. Photos are representative of previously built/sample home and may show options not included in the Supreme Spec package.
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.
914-238-4766
Location, Location, Location! Chestnut Oak Complex. Dramatic and bright townhouse with natural lighting. This 1 bedroom 1.1 bath plus huge Loft/Den is in mint condition. Updated kitchen with stainless-steel appliances. Living room with high ceilings, fireplace and wall of windows is combined with spacious dining area. Updated powder room on the first level. Huge primary bedroom with with two clothes closets and private updated full bath. Loft/Den/Office off primary bedroom with sliding glass door to balcony. This unit comes with one-car garage, newer furnace, hot water heater, refrigerator. Washer and dryer in the unit. Entire interior of the unit was just painted (September 2025). Complex offers, pool, tennis and community garden. Conviently located to Chappaqua train station, shopping, schools, parkways and bus.
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 10514has a population of 3,062. Chappaqua 10514 is more family-centric than the surrounding county with 46.13% 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 10514 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 10514 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.
