Chappaqua, NY Homes for Sale with Acreage

Meticulously maintained, beautifully appointed 4-bedroom, 4 full and 1 half-bath Colonial set on a level acre at the end of a quiet cul-de-sac in prestigious Inglenook Farm in the coveted Byram Hills Schools. A grand and light-filled two-story entry welcomes you into this refined home featuring 9-foot ceilings on 1st and 2nd levels, oak flooring, and custom moldings and trim throughout. Formal

Cindy Glynn Compass Greater NY, LLC

Located in the coveted Whippoorwill estate area, 61 Carolyn Place presides on 2.19 manicured acres and overlooks the Whippoorwill Country Club’s private golf course. Meticulous details abound with lofty ceilings and spacious rooms, complemented by warm, inviting, intimate spaces and outdoor areas. An open gourmet kitchen and breakfast room flow to the grand two-story family room and dedicated

Richard Hopple Julia B Fee Sothebys Int. Rlty

Welcome to 70 Haights Cross, an architectural masterpiece in one of Chappaqua’s most coveted neighborhoods. Designed by acclaimed architect Tasos Kokoris, this turn-key 5-bedroom, 7.2-bath colonial blends timeless elegance with today’s most sought-after amenities. Nestled on over two acres of private, professionally landscaped grounds, the property showcases a resort-like setting with a Gunite

Wendy Nolan Houlihan Lawrence Inc.

This sophisticated four-bedroom residence offers an ideal blend of convenience and tranquility just north of New York City. Enjoy the ease of walking to the vibrant village of Chappaqua—with its boutiques, cafes, and train station—while benefiting from the highly regarded Pleasantville School District. Commuting is effortless with the Chappaqua station mere minutes away and seamless access to the

Sari Shaw Compass Greater NY, LLC

Timeless elegance meets modern comfort in this beautifully updated Colonial home. Double entry front doors open to a gracious foyer, setting the stage for the home’s expansive and light-filled layout. At its center, the renovated chef’s kitchen impresses with gleaming Caesarstone countertops, professional-grade stainless steel appliances, dual dishwashers, an oversized island with prep sink,

Jennifer Harris Compass Greater NY, LLC

Welcome to this sophisticated 4-bedroom, 3.5-bath contemporary residence, perfectly designed for today’s lifestyle with a seamless blend of modern style and functional comfort. Set on a gracious property, this home offers open, luminous living spaces flooded with natural light and thoughtful architectural detail throughout. At the heart of the home, a beautifully appointed kitchen opens to a

Sari Shaw Compass Greater NY, LLC

Welcome to 58 Spring Lane – A stunning chalet-style retreat nestled at the end of a private lane just a short walk from the town of Chappaqua and Metro North train. This special home exudes timeless elegance and abundant period charm with its cathedral-vaulted ceilings, original gothic doors, expansive windows and versatile entertaining spaces. The main floor primary suite is a true sanctuary –

Catherine Orsini Compass Greater NY, LLC

Nestled in breathtaking natural surroundings, this modern architectural masterpiece by renowned designer Myron Goldfinger offers three levels of striking contemporary design. The residence features a soaring three-story curved ceiling, a dramatic floating staircase, and expansive open-plan living and entertaining spaces that frame the home’s private setting. The main-level primary suite provides

Tianying Xu Houlihan Lawrence Inc.

Welcome to 56 Annandale Drive, Chappaqua, a capacious and captivating Cape Cod commandingly set on 1.4 acres in sought-after Lawrence Farms East within walking distance to Mount Kisco Country Club, Kittle House, Chappaqua Crossing, Horace Greeley High School and the town of Mount Kisco. Built for entertaining, every day is a holiday to celebrate in the open, spacious interiors, starting with the

Stacy Levey William Raveis-New York, LLC

Hywood Ledge is a spectacular expanded ranch in the desirable Deepwood neighborhood of Chappaqua, which presents sophisticated charm and tranquility. This cedar-shake beauty is perfectly situated at the end of a cul-de-sac on 1.9 acres, offering unparalleled privacy, yet only 5 minutes to the center of town and the Chappaqua Metro-North. The home was renovated between 2000-22 offering years of

Brendan Preston 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

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