21 properties for sale in Chappaqua

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 isl

Welcome home to Chappaqua's best kept secret right in town! This classic 1989 center hall colonial has been reimagined for the way we live today, blending sun drenched, open spaces with effortless modern style, all less than a mile to the charming village, convenient train and public library. Step inside to a first floor that flows beautifully from room to room. The open concept living and dining rooms and kitchen bask in natural light all day long, anchored by a striking fireplace that begs for cozy evenings in. Need a smaller spot to unwind? The family room off the kitchen is the perfect retreat for movie nights and quiet mornings. The chef's kitchen is where this home truly shines, with a generous island for gathering and doors that open onto a sprawling deck. From there, steps lead down to a private yard, made for summer barbecues, morning coffee, and everything in between. Indoor outdoor living has never felt so seamless. A well appointed laundry room and stylish half bath round o

Attention builders! Grab your hard hats! Build your dream home on a desirable cul de sac street in Chappaqua School District! 4 bedroom septic approved! Reach out today for more information!

Soaring ceilings, a striking stone fireplace, and expansive windows overlooking mature trees define the character of 1 Whippoorwill Lake Road. Set on approximately 1.83 acres in Chappaqua, this five-bedroom contemporary offers approximately 3,423 square feet of living space, with natural materials and distinctive architecture creating a home of warmth and individuality. The living room is the architectural centerpiece. A towering stone fireplace anchors the space, while vaulted ceilings and an open upper gallery create a memorable sense of volume. Hardwood floors and rich wood detailing bring warmth to the airy interior, and sliding glass doors extend the living experience outdoors. The spacious eat-in kitchen pairs warm wood cabinetry with dark countertops, a paneled refrigerator, and a broad bank of windows that frames the surrounding greenery. There is room to linger over breakfast or gather while dinner comes together. A separate dining room, featuring an inviting window seat and g

SoHo in Chappaqua! Chappaqua schools! Dramatic, Airy and Light-filled 3 Bedroom Contemporary in immaculate condition located in sought-after neighborhood and Cul-De-Sac. Set on almost an acre of private property with rocking-chair front porch. Elegant living room features a soaring cathedral ceiling, wall of built-in bookshelves and wall of windows opening to dining area with access to deck. Renovated eat-in-kitchen offers granite countertop, pantry closet, stainless steel appliances and breakfast area with access to deck. Large family room with wood stove and custom mantle. Den/Office/Study with closet and renovated new bath completes the first floor. Primary bedroom with walk-in-closet, an additional closet and freshly renovated in-suite full bathroom. Two addditional bedrooms with renovated Jack-and Jill bath. Full semi finished lower level with Library and Recreational/Gym room 281sqft with CO (included in total). This exceptional home with wall of windows, skylights, high/cathedra

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 intr

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 offi

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 isl

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

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 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 burni

A private drive leads to your own secluded oasis. 35 Marcourt is a picture perfect colonial tucked away in a peaceful wooded setting located in the coveted Dodge Farm neighborhood. This home is filled with character, charm and architectural details making it one-of-a-kind. The classic center hall opens to both the formal dining room and a living room with a beamed ceiling, custom built-ins and a wood burning fireplace. Spectacular family room is flooded with light from skylights in the cathedral ceiling, three walls of windows and doors to the patio. A bright kitchen opens to the back porch overlooking the rear yard and adjacent to a brick patio with a built-in grill. An added bonus on the first floor is a den/office or guest suite with a beamed ceiling, built-in bookshelves and en-suite bath. Upstairs is a primary bedroom and bath, two bedrooms with double exposures and a hall bath. This home is a move-in ready gem just minutes from the village and train

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 intr

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

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 burni

Approached by a long private driveway and set on more than two beautifully landscaped acres, 46 Annandale Drive is a distinctive Lawrence Farms East residence offering approximately 7,500 square feet of thoughtfully designed living space. This five-bedroom Colonial has been thoughtfully expanded and maintained, with generous proportions, quality details, and excellent spaces for both everyday living and entertaining. The expansive first floor features generously proportioned versatile rooms. The eat-in kitchen with breakfast nook connects to a spacious great room with fireplace and direct access to the bluestone patio, while a formal living room with fireplace also opens to the patio, creating a natural connection between the interior and beautifully landscaped grounds. A large formal dining room provides an ideal setting for entertaining, while two additional multi-use rooms with custom built-ins offer versatile space for offices, family rooms, or other needs. A private guest suite, l

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

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

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!

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 pro

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

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted