Chappaqua Real Estate

Welcome to Chappaqua, New York – a charming hamlet nestled in the heart of Westchester County, just a short train ride from the bustling energy of New York City. Known for its picturesque landscapes, top-rated schools, and a strong sense of community, Chappaqua is the ideal place for families, professionals, and anyone seeking a tranquil suburban lifestyle.

With its tree-lined streets and historic homes, Chappaqua exudes a quaint, small-town charm that captivates residents and visitors alike. The area is rich in history, with its origins dating back to the early 18th century. Today, you can explore its vibrant downtown, featuring an array of boutique shops, delightful cafes, and gourmet restaurants that cater to diverse tastes.

Chappaqua is also renowned for its outstanding educational institutions, including the highly regarded Chappaqua Central School District, which consistently ranks among the top in the state. This commitment to education not only attracts families but also fosters a culture of lifelong learning and community involvement.

For nature enthusiasts, Chappaqua offers an abundance of outdoor activities. With numerous parks, hiking trails, and scenic spots, residents can enjoy the beauty of the Hudson Valley throughout the year. The nearby Rockefeller State Park Preserve provides ample opportunities for hiking, biking, and connecting with nature.

Whether you’re looking for a serene place to raise a family, a vibrant community to call home, or simply a beautiful area to explore, Chappaqua is a hidden gem that promises to enchant you at every turn. Discover the charm of Chappaqua – where community, culture, and nature come together harmoniously.

Newest Listings in Chappaqua

$829,000

3 Beds ⋅ 3 Baths ⋅ 1060556 MLS

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!

4 Hillside Place, Chappaqua

$1,396,000

3 Beds ⋅ 3 Baths ⋅ 1063202 MLS

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.

676 Hardscrabble Road, Chappaqua

$3,995,000

5 Beds ⋅ 6 Baths ⋅ 1031593 MLS

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 burning fireplace, and French doors to an expansive patio overlooking the orchard-like grounds. The adjoining eat-in kitchen offers an oversized island and sunlit breakfast area. A four season room with walls of windows and an adjacent office with a striking marble fireplace provide additional exceptional spaces. Two renovated powder rooms , a laundry room , and a spacious mudroom with side porch access and a three-car heated garage complete the first floor. The second floor features a luxurious primary suite with an oversized and vaulted ceiling bathroom, expansive walk-in closet, and two additional closets, plus four generously sized bedrooms, two with exquisitely renovated en-suite baths and a second family room. The finished lower level includes a large recreation room, home gym, full bathroom, and enormous storage. Outside, custom designed landscaping and property lighting, sweeping lawns, specimen trees , and flowering gardens create a private oasis, complemented by expansive bluestone terraces, a fire pit and a generous patio ideal for entertaining and outdoor enjoyment. Significant improvements include a driveway, Azec trim, freshly painted exterior, roof , comprehensive drainage system , stone retaining walls, boiler and condensers . Ideally located minutes from Chappaqua town, the train, and major highways, and less than an hour commute from Manhattan this exceptional property is situated within the award-winning Chappaqua Central School District . A truly rare offering combining refined living, remarkable space, and extraordinary privacy in a premier location. For the discerning buyer.

9 Trails End, Chappaqua

$3,088,000

7 Beds ⋅ 7 Baths ⋅ 1055737 MLS

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.

301 Roaring Brook Road, Chappaqua

$2,790,000

6 Beds ⋅ 6 Baths ⋅ 1035591 MLS

An extraordinary original Myron Goldfinger commission, documented in the architect’s archive as the 1991 Leff Residence, Architecture in the Landscape #7. This exceptional 8,200-square-foot contemporary residence showcases Goldfinger’s signature geometric design, dramatic curved ceiling, sculptural floating staircase, and expansive walls of glass that connect the interiors to the surrounding landscape. Six bedrooms and five-and-a-half baths include an exceptional main-level primary suite, offering a private retreat with a spectacular boutique-style walk-in dressing room featuring multiple custom closets, thoughtfully designed storage, and dedicated display spaces for shoes, handbags, and accessories. A truly special luxury feature not to be missed. The updated kitchen respects the integrity of the original architecture. Resort-style amenities include a private pool with two built-in grills, fitness room, and private tennis court, plus a four-car attached garage. Set in a remarkably private wooded setting in the Chappaqua Central School District, including Horace Greeley High School, with approximately 50-minute Metro-North access to Manhattan. A rare opportunity to own a significant work of architecture where privacy, nature, and extraordinary design converge.

20 Bessel Lane, Chappaqua

$1,599,000

8 Beds ⋅ 8 Baths ⋅ 1052500 MLS

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 intrigue to a home that already feels as though it has a story to tell. Inside, the expansive layout unfolds room after room, offering a rare canvas for someone with vision. This is not a house that asks to become something ordinary. Thoughtfully restore its classic character, reimagine it for modern living, or create a home that blends the best of both. With this much space, presence and possibility, the opportunities are endless. And then there is the location. Tucked behind its blanket of trees, 600 Bedford Road feels wonderfully removed, yet Chappaqua and Mount Kisco are both just minutes away. Metro North, shopping, dining, recreation and the conveniences of both villages are within easy reach, all within the Chappaqua Central School District. Homes of this scale and character are increasingly difficult to find. For decades, 600 Bedford Road has quietly waited and now it's time for it's next chapter to begin.

600 Bedford Road, Chappaqua

$2,299,000

5 Beds ⋅ 5 Baths ⋅ 1036792 MLS

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.

20 Hitching Post Lane, Chappaqua

$5,750,000

6 Beds ⋅ 8 Baths ⋅ 1017994 MLS

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.

24 Trails End, Chappaqua

$1,749,000

4 Beds ⋅ 4 Baths ⋅ 1044050 MLS

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.

406 Bedford Road, Chappaqua

$1,665,000

1038452 MLS

Extremely rare and ultra-private 12.92 acres of waterfront land in the Whippoorwill Lake enclave of Chappaqua. An exceptionally private canvas for a one-of-a-kind secluded getaway compound. Beyond the gate, a long private drive ascends to a concealed building site with sweeping lake and woodland vistas, plus natural water features including a waterfall and bridge. Near Whippoorwill Park, Chappaqua’s largest preserve (169 acres) and adjoining other protected woodlands. Minutes to Chappaqua, Armonk, and Mt. Kisco, express NYC commute and just 15 minutes to Westchester County Airport. Choice of Chappaqua or Armonk schools. The land sits within the Croton Watershed. An optional, stunning modern architectural package designed specifically for the site to maximize bucolic views. Full plan set and renderings available under separate agreement ($250,000). A truly one-of-a-kind and rare offering. Showings by appointment only for discerning, qualified buyers with verified proof of funds. Ideal for those seeking to build a custom private compound or a bespoke retreat.

767 King Street, Chappaqua

$1,490,000

3 Beds ⋅ 4 Baths ⋅ 1017997 MLS

$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 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.

131 Douglas Road, Chappaqua

$1,849,000

1005784 MLS ⋅ 21 BLDG.

Investment opportunities like this rarely become available in Downtown Chappaqua. Welcome to 21 King Street, a rare mixed-use commercial property offering exceptional visibility, convenience, and income potential in one of Westchester's most desirable downtown locations. The building features two street-level retail storefronts and a residential apartment above, creating multiple income streams and long-term investment value. A standout feature is the private rear parking lot accommodating approximately 14 vehicles—an increasingly valuable asset in downtown Chappaqua. In addition to serving the property's tenants and customers, the parking area may offer additional income potential through rental opportunities. The rear lot also presents future upside, as it may provide opportunities for expansion or redevelopment, subject to municipal approvals and zoning requirements. Ideally positioned just moments from shops, restaurants, and the Metro-North train station, 21 King Street benefits from excellent foot traffic and a highly sought-after location. Whether you are an investor seeking diversified income streams, an owner-user looking to establish a presence in Chappaqua, or someone searching for a prime long-term asset, this is a unique opportunity to own a landmark property in the heart of town with both immediate cash flow and future potential.

21 King Street, Chappaqua

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Chappaqua Real Estate

Newest Listings in Chappaqua

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