Chappaqua 5 Bedroom Properties for Sale

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Newest Chappaqua 5 Bedroom Properties for Sale

$3,100,000

5 Beds ⋅ 6 Baths ⋅ 990281 MLS

Privately gated and masterfully crafted, this exceptional custom brick estate is a showcase of timeless elegance and grand-scale living, nestled on over two acres in the heart of Chappaqua. Beyond the cobblestone apron and curbing, a sweeping driveway leads to a residence designed for both luxury and comfort, boasting soaring 10-foot ceilings, four stately fireplaces, exquisite architectural detail, and refined finishes throughout. Enter through a breathtaking grand foyer, where gleaming hardwood floors with intricate wood inlay medallion set the tone, and a dramatic three-story suspended spiral staircase anchors the home in architectural splendor. The main level is ideal for entertaining, offering a formal living room, formal dining room, an expansive family room with a custom bar, and seamless access to a private bluestone patio, perfect for indoor-outdoor gatherings. The chef’s kitchen is a culinary masterpiece, featuring high-end appliances, breakfast area, butler’s pantry, and dual access points to the patio. A main-floor guest/au pair suite, private office or den, and powder room complete the level. Upstairs, the serene Master Suite is a retreat unto itself, complete with a sitting area, dual walk-in closets, and a spa-like marble bath with heated towel racks, dual vanities, clawfoot soaking tub, and an oversized glass shower. Three additional generously-sized bedrooms, one with an ensuite, and a full hall bath, along with a dedicated laundry room, offer both comfort and convenience. The third floor adds a spacious game and media room, while the walk-out lower level features a gym, mudroom, recreation space, sitting area, and access to the beautifully landscaped backyard. Outside, enjoy artisan stonework, multiple patios, a gazebo, hot tub, built-in BBQ station, and lush, level grounds ideal for entertaining and play. Three heated garages, including an electric vehicle charging station, complete this extraordinary masterpiece with modern convenience and sophistication. Located just minutes from Chappaqua’s charming village center, award-winning schools, fine dining, shopping, Mt. Kisco Country Club, Metro North, and major highways. This is a a rare opportunity to own one of Chappaqua’s most distinguished estates, an architectural triumph of timeless sophistication and commanding presence, set within one of Westchester’s most coveted communities.

2 Heathcote Drive, Mount Kisco

$1,100,000

5 Beds ⋅ 3 Baths ⋅ 991248 MLS

Some homes have good bones. This one has great ones in a private setting. Nestled in Chappaqua's beloved Seven Bridges neighborhood, this 1934 Colonial sits on nearly three-quarters of an acre where tree-lined streets and a true sense of community appeal to buyers who embrace Chappaqua and remain for years. Original hardwood floors, a wood-burning fireplace, crown molding, and a screened porch speak to craftsmanship that simply cannot be replicated. An updated kitchen with granite countertops, wood cabinetry, and a gas range bring real functionality to the floor plan. Main floor offers living room with attached screened in porch, formal dining room, family room / breakfast room, kitchen, huge en-suite bedroom and laundry room. Upstairs holds four more bedrooms, primary ensuite and another full bathroom. Basement has slop sink with laundry hook up and mechanicals. A 2-car garage with a huge walk-up attic, and two additional attics accessed from inside the home give you the space and storage to match your needs. Bring your vision and make it yours in one of Westchester's most sought-after school districts.

2 Turner Drive, Chappaqua

$4,500,000

5 Beds ⋅ 7 Baths ⋅ 950756 MLS

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!

150 Old Farm Road N, 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.