luxury houses for sale Chappaqua, United States

Welcome to Pleasantville! Tucked at the end of a picturesque cul-de-sac, this move-in ready home offers exceptional privacy, abundant natural light, and modern comfort throughout. With 4 bedrooms, a dedicated home office, and 3 full baths, it's thoughtfully designed for today's lifestyle. The sun-filled main level features an expansive living room with oversized picture windows and a beautifully updated eat-in kitchen with rich cherry wood cabinetry. The kitchen flows seamlessly into an open dining area—perfect for everyday living and entertaining—while a separate formal dining room offers flexible use as an additional sitting area or den. Step outside to a deck and large patio overlooking a private backyard, ideal for effortless indoor-outdoor living. A half-flight down from the kitchen leads to a versatile bonus level with an additional bedroom, office space, large laundry room, utility room, and a well-placed mudroom for everyday convenience. Upstairs, the generous primary suite includes a Juliette balcony, walk-in closet, two additional closets, and a private en-suite bath. Two additional bedrooms and a full hall bath complete this level. The expansive lower level offers even more flexible living space, featuring a recreation room with sliding doors that open to a paver patio. Set on beautifully landscaped, park-like grounds with mature plantings, this home combines tranquility with convenience. Just minutes from downtown Pleasantville and the Chappaqua train station, it offers easy access to shopping, and dining and more.

Welcome to Pleasantville! This beautifully maintained 5-bedroom, 2-bathroom home is set on a generous 0.35-acre lot and offers space, comfort, and exceptional value in a tranquil setting. Step into a light-filled living room featuring an oversized bay window, creating a warm and inviting atmosphere. The space flows seamlessly into a formal dining area, perfect for gatherings. Glass sliders open to a private deck—ideal for morning coffee or evening entertaining. The eat-in kitchen provides ample cabinetry and counter space, making it both functional and enjoyable. A cozy lower-level recreation room offers flexibility as a home office, or den. The lower level also features a walk-out basement with private laundry and direct access to a large paved patio. Upstairs, you will find five generously sized bedrooms, each with plenty of closet space. The primary bedroom features a private deck that doubles as the roof of a covered carport below. Outside, enjoy a beautifully manicured yard surrounded by mature trees, offering both privacy and charm. Conveniently located near schools, parks, and the train station with easy access to Manhattan, this home combines peaceful suburban living with commuter-friendly convenience.

Move right into this beautifully updated Colonial and start enjoying life in one of Pleasantville's most convenient locations—Just a 1/2 mile from the Metro-North train station, Pleasantville's acclaimed restaurants, shops, the Jacob Burns Film Center, and Saturday's Farmers Market. Inside, the home feels bright, easy, and welcoming from the moment you step in. Gleaming hardwood floors and custom details set the tone, while the living room flows naturally into the dining room with built-ins and a cozy window seat—perfect for everyday living or hosting friends. The updated kitchen brings it all together with a center island, wine fridge, and an open connection to the family room with a gas fireplace. Sliding doors lead right out to a Trex deck and level, fenced-in yard—great for barbecues, play, or just unwinding. Upstairs, the primary suite is a true retreat with a walk-in closet, private bath, lots of natural light, and a tray ceiling. Three additional bedrooms with custom closets share a full hall bath and complete the second floor. Downstairs, the finished lower level adds approximately 800 sq. ft. of finished storage space with access to the one-car garage. With a full-house generator and thoughtful upgrades throughout, everything is ready for you to move in and enjoy from day one. This turnkey gem is not to be missed.

Welcome to 10 Crestview Drive, a beautifully updated 1990 colonial that perfectly blends classic elegance with updated modern luxury within the highly sought-after Heritage Court neighborhood. This exceptional property offers the rare combination of an intimate community feel and tremendous, serene privacy, all set on nearly an acre of flat, meticulously manicured grounds. Inside, you will find a bright and spacious layout featuring four well-proportioned bedrooms, all on the same level, and designed for ultimate comfort. The main floor features a three-car garage, mudroom, eat-in-kitchen with easy access to the deck, and backyard beyond, open floor plan, living room, dining room, and office. Also of note, this turnkey gem provides an unparalleled and truly unique opportunity for the next lucky buyers: a rare, one-time option to choose between the Chappaqua or the Byram Hills School District at closing. This is turnkey luxury at its finest!

Welcome to 20 Robbins Road—perfectly set on a quiet cul-de-sac on a half-acre with a fenced in backyard in one of Westchester’s most desirable communities. Step inside to an inviting living and dining area where oversized windows and a cathedral ceiling with skylight fill the space with natural light. A cut-stone fireplace, recessed lighting, and oak floors create a warm, stylish setting for everyday living and entertaining. At the heart of the home, the spacious chef’s dream eat-in kitchen impresses with cherry wood cabinetry, quartz countertops, skylight, slate tile floors, and premium stainless appliances including a six-burner Viking range, GE Monogram refrigerator, wine cooler and Bosch dishwasher. Sliding doors open to an attractive Trex deck overlooking the serene rear property—perfect for summer dining and weekend gatherings. The main level is completed with three bedrooms, including an oversized primary suite, and an updated hall bath. The primary suite offers a generous walk-in closet with pocket door, ceiling fan, custom cabinetry, a wall of windows for abundant light, and a window seat with additional storage, plus a gorgeous updated en-suite bath. Downstairs, enjoy a spacious recreation/TV room with beadboard trim and sliders to the backyard. A paver walkway leads to a patio designed for effortless outdoor entertainment. A second family room/TV space features built-in custom cabinetry and vinyl floating flooring. The lower level also includes an office/bedroom, laundry area, and an updated bath—ideal for guests, work-from-home, or multi-generational flexibility. Just minutes from vibrant downtown Pleasantville—dining, the Jacob Burns Film Center, schools, library, shopping, farmers market, and community pool—with easy access to the Metro-North train station, Saw Mill River Parkway, and Sprain Brook Parkway.

Steeped in local history and once owned by the Gilded Age Van Cortlandt family, gracious Rose Lodge is an inviting and beautifully restored historic estate—not landmarked—offering modern living and exceptional privacy on 17.9 acres. The property enjoys sweeping views across a perfectly sited in-ground pool, terraced gardens, expansive flat croquet lawn, and private lake, creating a serene country setting less than an hour on the express train from NYC. The main residence features a warm and welcoming checkerbox marble foyer opening to elegant formal rooms, and flowing to a cozy bar and family room overlooking the grounds through walls of windows. A sparkling chef's kitchen, convenient butler's pantry, and finely restored period details make the home ideal for both everyday living and entertaining. Upstairs, there is extensive accommodation, including a spacious primary suite with elevated views of the private lake, along with three additional bedrooms and multiple baths. A generous home office and dedicated home theater provide exceptional flexibility for work and leisure. The uppermost floor offers two more expansive bedrooms, or flex space for a creative studio. Beyond the main residence, the estate includes a 5-car garage connected to a stables complex by an elegant breezeway. An additional and completely remodelled 1-bedroom apartment above the stable wing, and a charming separate 2-bedroom stone cottage provide versatility for guests, multigenerational living, or rental/Airbnb income. Landscaped grounds with nature paths, sweeping lawns, and exceptional stonework make this a true retreat. Located in the quaint riverfront community of Ossining, known for its scenic Hudson views, vibrant downtown, and abundant parks and trails, this property offers a rare opportunity to own a thoughtfully preserved and modernized Hudson Valley estate.

Come home to this stylishly updated cedar shake colonial with a great open layout. Located on a beautiful and flat lot at the end of a quiet private road within the Byram Hills School District, this home blends country charm with effortless convenience. Gracious entry leads to an open main level featuring a living room with woodburning fireplace, dining room, spacious eat-in kitchen opens to the great room, perfect for everyday living and entertaining alike. Upstairs, a private primary suite with en-suite bath, and large WIC is joined by two additional bedrooms and an updated full bath. A separate office or Bonus room offers flexibility. Additional 547sq ft in basement(laundry and storage) Outdoors you will find a new slate patio for BBQ's and lounging, lush lawns, plenty of play spaces and blooming perennials. All just minutes from trains, towns of Armonk, Pleasantville and Chappaqua and one of the district's easiest commutes.

Luxury rental living in downtown Briarcliff Manor! This brand new construction elevator building is a unique boutique-style rental opportunity. Unit 2C is a one bedroom apartment featuring an open layout. This corner unit is bright and sunny thanks to the large windows bringing in natural light. As you step inside, you'll be greeted by a large custom kitchen boasting high-end stainless appliances and a large island with quartz countertops. The interior is thoughtfully designed with WASHER/DRYER in the unit for added convenience. The bathroom is a true retreat, featuring radiant heated floors, lighted medicine cabinet and custom tile design. Individually controlled ductless high-efficiency heat and a/c units. For security and convenience, the building is equipped with a video intercom system. Walk-to-town, shops, restaurants. Pets allowed under 25lbs. Free municipal parking directly behind the building or indoor paid parking is available for $125/month. EVERY UNIT RECEIVES A FREE STORAGE UNIT IN THE BUILDING! Photos of similar units in building with same finishes. Check attached floor-plan for exact layout.

Luxury rental living in downtown Briarcliff Manor! This brand new construction elevator building is a unique boutique-style rental opportunity, with only 8 units available. Unit 3A is a two bedroom apartment featuring an open layout. This corner unit is bright and sunny thanks to the large windows bringing in natural light. As you step inside, you'll be greeted by a large custom kitchen boasting high-end stainless appliances and a large island with quartz countertops. The interior is thoughtfully designed with full-sized WASHER/DRYE in the unit for added convenience. The bathroom is a true retreat, featuring radiant heated floors, lighted medicine cabinet and custom tile design. Individually controlled ductless high-efficiency heat and a/c units. For security and convenience, the building is equipped with a video intercom system. Indoor paid parking is available, or FREE PARKING directly behind the building. Walk-to-town, shops, restaurants,. Top-ranked schools and recreation facilities. Close proximity to Metro North into NYC. Pets allowed under 25lbs. EVERY UNIT RECEIVES A FREE STORAGE UNIT IN THE BUILDING!

Fully renovated LOFT one bedroom in downtown Briarcliff Manor! Exciting opportunity to be the first to live in this bright modern home with beautiful new bleached hardwood floors, new washer/dryer, new custom kitchen with quartz countertops and new stainless steel appliances including range, microwave, hood, French door refrigerator. Loft-style layout with kitchen open to the living area. Spacious bedroom with a large walk-in closet and new washer/dryer. Central heating and air-conditioning with the HVAC provided by an eco-friendly heat pump. A stunning apartment in an historic pre-war building conveniently located near Route 9 and the Taconic Parkway. Walk to restaurants, shopping and more! Parking on premises. Pets case by case.

Welcome to Pleasantville! This beautifully maintained 3-bedroom, 2-bathroom home offers space, comfort, and exceptional value in a picturesque setting. Step into a light-filled living room featuring an oversized bay window that creates a warm and inviting atmosphere. The space flows seamlessly into a formal dining area, perfect for entertaining and everyday gatherings. Glass sliders open to a private deck—ideal for morning coffee or evening relaxation. The bright kitchen features granite countertops and ample cabinetry, making it both functional and enjoyable for cooking and hosting. A spacious lower-level recreation room provides excellent flexibility for a family room, home office, gym, or den. The lower level also includes private laundry and a walk-out basement leading to a large backyard. Upstairs, you'll find three generously sized bedrooms, each offering abundant closet space. The primary bedroom includes its own private bathroom for added comfort and convenience. Outside, enjoy a beautifully manicured yard surrounded by mature trees, creating a peaceful and private outdoor retreat. Conveniently located near schools, parks, and the Metro-North Railroad station with easy access to Manhattan, this home perfectly blends suburban tranquility with commuter-friendly living.

Opportunity knocks on this exceptionally private, 2+ acre parcel tucked away on a serene street ending with a cul-de-sac in the sought-after Town of New Castle. Whether you are looking to take on a complete top-to-bottom renovation or build the custom home of your dreams, this property offers the perfect foundation and acreage for your vision. While you'll feel worlds away in your own private woodland retreat, you are minutes from the best of the Hudson Valley. Commuting is a breeze with easy access to the Taconic State Parkway and both the Ossining and Croton-Harmon Metro-North stations. Enjoy an unmatched lifestyle surrounded by local culture and nature. You're just a short drive from daily conveniences, schools, and parks, as well as other local highlights including Teatown Lake Reservation, Kitchawan Preserve, Sunny Ridge, the North County Trailway, the historic Jacob Burns Film Center and both Sleepy Hollow Country Club and Hudson National. Bring your architect, your contractor, and your imagination. Property being sold strictly as-is.

Experience the pinnacle of sophisticated living in this stunning residential masterpiece, perfectly situated on 6.27 expansive acres of lush, manicured grounds. Offering a rare blend of grand-scale entertaining spaces and intimate private retreats, this estate is a testament to quality craftsmanship and thoughtful design. The main level welcomes you with an effortless flow, anchored by an open-concept eat-in kitchen designed for the culinary enthusiast. Bathed in natural light, this space transitions seamlessly to the formal living areas, where two of the home's three elegant fireplaces create a warm, inviting ambiance. For added convenience and longevity of lifestyle, the main floor also features a refined home office, second laundry, and a full ensuite guest bedroom, perfect for overnight guests. The second level is a study in comfort, housing the additional four bedrooms, each boasting its own private ensuite bathroom. The primary bedroom suite is a true destination, featuring a cozy gas fireplace for quiet evenings and a spa-like atmosphere that defines luxury. Additional features include an upstairs laundry room and a large recreation area capable of serving as a second study or playroom. The finished lower level is an entertainer's dream, meticulously outfitted to serve every hobby and lifestyle need including a dedicated exercise room to maintain your wellness routine, a stylish wet bar and wine room, and a spacious game room designed for hours of amusement. Step outside to a backyard that rivals a five-star resort. An extensive flat lawn provides a canvas for play, framed by mature privacy screening that ensures total seclusion. The centerpiece is a vast raised bluestone patio overlooking a magnificent saltwater pool and spa. Finished with a shimmering quartz surface, the pool features a tranquil waterfall, while a retractable pool cover offers safety and efficiency at the touch of a button. While tucked away in your private park-like setting, you remain at the center of it all. This estate offers unparalleled proximity to the world-class dining, upscale shopping, and commuting centers of Armonk, Chappaqua, Mt. Kisco, and Bedford. Discover the perfect balance of rural tranquility and sophisticated suburban living. This is more than a home; it is a legacy.

Welcome to this meticulously maintained Colonial home in the heart of Pleasantville, offering modern, youthful style and the warmth of a true community. The light-filled interior is move-in ready, with four generous bedrooms, three full baths, and a convenient powder room designed for everyday living and effortless entertaining. The fully finished lower level expands the home's footprint with a spacious recreation room, dedicated workout space, and a full bath—perfect for guests, movie nights, or unwinding after a long day. Step outside to your own private retreat, where an expansive deck and sparkling pool area create the ultimate setting for summer gatherings and quiet weekends. Set in a neighborhood where Halloween is a tradition not to be missed. This home also falls within the highly regarded Byram Hills School District. A rare opportunity to own a turnkey home in one of Westchester's most sought-after communities.

Set majestically on nearly three gated acres in Armonk’s coveted Wrights Mill Estates, this extraordinary hand-cut stone manor with over 12,000 sq ft of classic architecture, artisan craftsmanship, and resort-caliber living. A breathtaking foyer leads to the two-story great room with an impressive window wall and fireplace. A richly paneled study and sunlit conservatory offer space for dual home offices. A family room, dining room, chef’s kitchen with pantry and breakfast room, complete the main level. The upper level offers a grand primary suite, a luxurious retreat featuring a fireplace, dual spa baths, separate dressing rooms, and a third-floor private wellness space with sauna. Additionally, upstairs, four ensuite bedrooms, laundry room and den are joined by a dramatic enclosed bridge leading to a private guest wing. The lower level rivals a private club with lounge, wet bar, wine cellar, theater, gym, hot yoga studio, bedroom, bath and second laundry. Outdoor amenities are designed for both relaxation and entertaining, featuring a beautifully integrated pool, an independent spa, expansive terraces and patios and a built-in outdoor grill. The flat, beautifully manicured grounds are complemented by an elegant courtyard with eight garage bays providing generous space for prized automobiles and collections alike. Combining timeless-inspired grandeur with modern luxury, this remarkable estate presents a rare opportunity to enjoy a private country-club lifestyle just minutes from downtown Armonk and Greenwich, with convenient access to New York City. A truly exceptional opportunity for the most discerning buyer.

Welcome to this truly stunning residence in Pocantico Hills, where timeless design meets modern updates-all complemented by remarkably low taxes. This exceptional home features four spacious bedrooms and four full baths, including a brand-new roof (January 2024) and a newly painted chef's kitchen designed for both function and style. At the heart of the home is the breathtaking Great Room, inspired by the historic Hingham Meeting House, showcasing intricate woodwork and soaring vaulted ceilings that create a dramatic yet inviting space. The main level offers a bright home office, a screened-in porch perfect for relaxing, and a full bath for added convenience. Upstairs, the primary suite serves as a private retreat, featuring a recently updated full bath (January 2026) and generous storage, including two cedar walk-in closets. Three additional bedrooms complete the upper level, two of which include their own en-suite full baths. The lower level provides abundant storage, while a separate Two-Story Guest House above the three-car garage adds incredible versatility, offering Two Additional bedrooms and two full baths—ideal for extended family or guests. Set on pristine, private grounds, the property is just moments from the scenic trails and outdoor beauty of Rockefeller State Preserve. Residents of Pocantico Hills benefit from a strong Pre-K through 8th grade program, along with high school choice options including Pleasantville, Briarcliff Manor, and Sleepy Hollow. The community also features exceptional amenities such as an Olympic-sized swimming pool, tennis and pickleball courts, basketball courts, playgrounds, and ball fields. 2 Brand Above Ground New Oil Tanks (May 2026) This is a rare opportunity to own a truly distinctive home!

Seize this rare opportunity to own an iconic estate rich in history, dating back to the 1890s. This distinguished property, known as The Manor House, was built for and live in by Walter Law, the founder of The Village of Briarcliff Manor. Constructed on Brier Cliff Farms, originally acquired from James Stillman, then-President of National City Bank (now Citibank), the estate at 139 Scarborough Rd exudes a blend of historical charm and opulence. Spanning over 9 acres, the expansive 15,000+ sq. ft. residence features 14 bedrooms, 7.1 bathrooms, a private entertainment hall, a bar, an atrium, and an indoor pool, all highlighted by distinctive architectural elements. The wood paneling throughout the estate, imported from The Baxter Church in England, has been meticulously preserved. In 1928, The Manor House served as a clubhouse for the Metropolitan Masons with a golf course on property and was once the venue for a notable boxing match between Jack Sharkey and Carl Brisson in the early 1930s. Designed with input from the Olmstead Brothers, renowned landscape architects behind Manhattan's Central Park, the estate still features remnants of their work, including waterfalls, retaining walls, statues, gazebos, and greenhouses. Neighbors to the Manor House have included prominent families such as the Rockefellers, Shepherds, Speyers, Macys, Webbs, and Astors. This is a rare opportunity to restore and own a significant piece of history. Don't miss the chance to make this extraordinary estate your own. Additional Information: HeatingFuel:Oil Above Ground, Property being sold As-Is.

Charming front porch colonial on tree lined Street. Front door opens to entry hall, large dining room and living room with hardwood floors, arched walkways between rooms. Beautifully updated kitchen with island and stainless appliances, half bath. A first floor bonus room that can be used as a bedroom or den/office. Upstairs leads to three bedrooms, a full bath, hardwood floors throughout, updated fixtures. Basement has laundry and utilities and storage space plus a playroom. The big deck outback looks over the yard parking for 3+ cars Taxes do not reflect basic star exemption of $1,555.

Gracious Brick Georgian Colonial, nestled on 2 resort-like acres with a gated drive, was designed for an elevated living experience. Throughout the home are generously sized spaces that seamlessly combine a sophisticated floorplan, perfect for everyday functionality, with tasteful finishes. The two-story grand foyer, anchored by a sweeping staircase and bathed in natural light, creates a striking first impression. The chef’s kitchen is a showstopper with exposed wood beams, custom cabinetry, high-end appliances, center island and adjacent service pantry with ample storage. An elegant arched opening leads you to the family room with stone fireplace and French doors out to an expansive deck. A warm home office with custom paneling and fireplace offers an additional space for work or study. The upper level boasts a primary suite, the crown jewel of this home, featuring tray ceilings, a dressing room with center island, and a truly magnificent spa-inspired bathroom complete with a sauna, soaking tub, and walk-in shower. 3 additional ensuite bedrooms, plus a bonus room complete this level. The lower level is for entertaining with a media room, bar, state-of-the-art gym, and a spectacular 3-season porch that leads to the patio and pool area. Outdoors showcases specimen plantings, stone walls, a heated Gunite pool and outdoor kitchen, perfect for relaxation and entertainment. Minutes to Armonk town center, schools and highways. 50 minutes to NYC.

Set within one of Armonk's most sought-after locations, this exceptional custom-built stone Colonial offers a rare combination of privacy, scale, and refined craftsmanship. Privately positioned behind a gated entrance on nearly five level acres, the property showcases sweeping lawns, newly designed landscaping, and breathtaking open vistas—creating an ideal setting for both everyday living and grand entertaining. A dramatic entry introduces the home's impressive interior, highlighted by a striking double floating staircase and a sun-filled, two-story living room with radiant heated floors. The thoughtfully designed open layout seamlessly connects formal and informal spaces, offering both elegance and comfort. At the heart of the home, the chef's kitchen flows effortlessly into inviting gathering areas centered around a timeless stone fireplace, with French doors leading out to an expansive stone patio complete with its own outdoor fireplace. The grounds are equally impressive, featuring a wide, usable backyard perfect for recreation or future enhancements, including an ideal pool site. Whether hosting large gatherings or enjoying a quiet afternoon, the outdoor spaces offer endless possibilities. Inside, the home features two luxurious primary suites—one on the main level and one upstairs—along with two additional bedrooms. Six full bathrooms and two powder rooms are beautifully appointed with high-end finishes, including marble baths, soaking tubs, and steam showers. The walk-out lower level is designed for both work and leisure, offering a spacious office, fireplace, home theater, and an elegant wine cellar. Additional highlights include radiant heated floors in select areas, abundant storage, and a heated three-car attached garage. Located just minutes from the heart of Armonk, with easy access to major roadways, Westchester Airport, and the North White Plains train station, this home combines serene estate living with everyday convenience. All within the award-winning Byram Hills School District.