6+ Bedroom Homes for Sale in Chappaqua, NY

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Welcome to your dedicated resource for 6+ bedroom homes for sale in Chappaqua, NY. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Chappaqua, NY agent, Tierra Stanback specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the 6+ bedroom properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All 6+ Bedroom Homes for Sale in Chappaqua, NY

$2,799,000

6 Beds ⋅ 5 Baths ⋅ 923774 MLS

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-front cabinetry, creating an elegant and functional space for everyday living and entertaining.The dramatic, wood beamed Family Room is a true highlight, with a fireplace and door to the patio. A first floor office/study, with ensuite bath, laundry room, mudroom and renovated powder room complete the first floor. On the second floor, the light-filled primary suite offers a door to a balcony and renovated en-suite bath with radiant heat and steam shower, is complemented by four additional generously proportioned bedrooms. Two renovated full baths and a gym/office complete the second floor. With lots of multi-use rooms, this home offers exceptional flexibility for guests, home offices, and additional living needs. Set on approximately two acres of level, park-like property, the grounds feature expansive lawns with abundant room for play, recreation, and relaxation, complemented by an inviting fire pit, elegant stone walls, and a welcoming patio— all framed by mature trees and lush natural surroundings. The remarkable setting combines the beauty of a private estate with the convenience of a coveted neighborhood location. Substantial recent upgrades include a new roof (2025), new boiler (2025), ductless split air-conditioning systems (2024) and generator. Natural gas utilities, a detached two-story garage with exceptional bonus storage space above, and an EV car charger add further convenience. Enjoy an enviable location within walking distance of Horace Greeley High School, Mount Kisco Country Club, the renowned Crabtree's Kittle House, and Chappaqua Crossing, featuring Whole Foods, Life Time Fitness, the Chappaqua Performing Arts Center, and an array of additional shopping and dining options. A truly exceptional offering that combines distinguished Colonial architecture, sophisticated updates, generous living spaces, and magnificent private grounds in one of Lawrence Farms East's most desirable settings.

18 Ivy Hill Road, 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

$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

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.