Chappaqua, NY Homes for Sale with Acreage

Timeless elegance meets modern comfort in this enchanting 1901 hunting lodge, masterfully restored in 1991 and recently enhanced. Set on beautifully landscaped grounds with lush gardens, this distinguished home features a dramatic front portico, high ceilings, intricate millwork, and unique architectural details throughout. Grand living spaces include a library/home office with French doors and

Joshua Rogull Julia B Fee Sothebys Int. Rlty

50 Overlook Drive, an elegant 6-bedroom colonial Tudor set in a quiet, tree-lined neighborhood. With fresh upgrades completed this month, including interior repainting, carpet-removal to expose wood floors. This one-of-a-kind home is a must see. Meticulously maintained heating and cooling systems, brick exterior, and a classic-tile roof are some of the exceptional features this home can

Wendy Nolan Houlihan Lawrence Inc.

Tucked away in a 3+ acre private storybook setting, this reimagined farmhouse blends timeless charm with modern comfort. Set back from the road on a scenic, private property with gorgeous mature landscaping, two tranquil ponds, and wide-open views, this 4-bedroom home is a peaceful retreat unlike any other.Inside, the open, sunlit layout features oversized windows that invite the outdoors in,

Sari Shaw Compass Greater NY, LLC

Exceptional and sophisticated Nantucket shingle style Colonial on 3.66 private acres in one of Chappaqua’s most desirable neighborhoods, offers the perfect balance of casual elegance and resort-style living. Just 45 minutes from NYC and minutes to town, train, and top-rated schools, this turnkey home offers unmatched convenience and luxury. Designed for both everyday comfort and effortless

Cindy Glynn Compass Greater NY, LLC

This distinguished 7,300-square-foot Colonial residence, constructed in 2007, is ideally situated on a level, professionally landscaped property, offering a rare blend of timeless architectural elegance and modern luxury. Meticulously designed and impeccably maintained, this exceptional home features four en-suite bedrooms with space for a fifth , a spacious bonus room/office, and a thoughtfully

Sari Shaw Compass Greater NY, LLC

Welcome to 56 Annandale Road – a sleek & sophisticated Contemporary Colonial tucked into the prestigious Lawrence Farms East enclave, with panoramic views of the Mount Kisco Country Club’s fairways & pool. This rare offering delivers a perfect blend of privacy, style, & convenience in one of Westchester’s most sought-after communities. Set on almost an acre & a half of beautifully landscaped

Michael Levy eXp Realty

Welcome to 70 Haights Cross, a stunning turn-key 5 bedroom, 7.2 bath colonial designed by noted architect Tasos Kokoris. Located in a coveted neighborhood, this home is set on 2 plus private professionally landscaped acres with a Gunite pool with waterfall and jacuzzi. The heart of the home lies in the gourmet kitchen featuring a Wolf-6-burner range, warming and fridge drawer, 2 Bosch dishwashers

Wendy Nolan Houlihan Lawrence Inc.

Experience the pinnacle of refined living in this newly reimagined modern farmhouse, perfectly sited on a secluded, tree-lined acre in the heart of Chappaqua. With over 2,800 square feet of exquisitely finished space, this residence blends timeless architectural detail with sophisticated, high-end design for the ultimate in quiet luxury. Andersen 400 series windows and doors throughout, most are

Aric Wiser Douglas Elliman Real Estate

Welcome to this beautifully updated and meticulously maintained 3-bedroom Colonial that lives like a four-bedroom, ideally located on a quiet cul-de-sac with quick access to town, schools, and train.Step inside to discover a spacious and inviting layout featuring gleaming hardwood floors throughout, two wood-burning fireplaces(one in the formal living room, one in the finished lower

Krystyna Biziaieva Compass Greater NY, LLC

Nestled on over 5 private, professionally landscaped acres in the exclusive cul-de-sac of Sutton Farm within Chappaqua’s esteemed Whippoorwill area, this custom-designed and custom-built Shingle Style home is a rare and refined first opportunity. Completed in 2008 by a renowned builder and architect, the 4+ bedroom home (lives like a 5/6) has been meticulously detailed with luxurious, high-end

Cindy Glynn Compass Greater NY, LLC

This charming cottage has been completely reimagined, seamlessly blending timeless character with modern luxury. Fully gut-renovated and thoughtfully redesigned from top to bottom, this inviting home offers the perfect retreat—whether you're seeking a serene weekend escape or a full-time residence.Ideally located just minutes from downtown Chappaqua and seconds from Chappaqua Crossing, Horace

Christine Anderson Compass Greater NY, LLC

This beautiful Chappaqua house sits on 3.25 acres surrounded by formal gardens and woods. Designed by the renowned Westchester architect James Renwick Thomson in the 30's, this home seamlessly incorporates both elements of formal sophistication along with more casual charm. It is a one-of-a-kind gem, containing Palladian windows, vaulted ceiling, custom wood work, bay windows, Dutch doors,

Douglas Dill Houlihan Lawrence Inc.

Welcome to 26 Mayberry Road, a charming and spacious 5-bedroom expanded ranch-style home on a quiet cul-de-sac street in the Chappaqua school district. Set on a private, landscaped acre, this home offers scenic views from the elevated deck and large stone patio just off the walkout lower level. The main floor features a versatile and inviting layout with formal living and dining rooms, a kitchen

Edward Holmes William Raveis-New York, LLC

Turn-key, custom-built 5-bedroom center-hall colonial in Chappaqua’s desirable Hardscrabble Lake community. First floor includes an open floor plan between the updated kitchen and family room with wood-burning fireplace and sliders to the oversized, new Trex deck, a large living room with french doors to the library with access to the deck, formal dining room, powder room, mudroom and door to

Nancy Strong Douglas Elliman Real Estate

A dramatic and stunning four-bedroom Contemporary home set on 1.2 professionally landscaped acres, designed by Jan Johnsen, former landscape architect for the New York Botanical Gardens. Surrounded by wooded privacy, this serene setting features two separate decks and a ground-level patio that surrounds the exterior of the home. Inside, this home offers a light-filled, modern, and open layout

Edward Holmes William Raveis-New York, LLC

Welcome to 10 North Lane — a spacious 3-bedroom, 3-bath home offering 3,155 square feet of comfortable living in the heart of Chappaqua. Located within the highly acclaimed Chappaqua School District, this charming residence is perfectly positioned on a quiet, private dead-end street just minutes from the Taconic Parkway, shopping, and the vibrant Chappaqua town center. Enjoy a beautifully level

Annette Cicinelli Keller Williams Realty Partner