Chappaqua, NY Homes for Sale

Refined and elegant Circa 1927 Colonial, nestled on one of Chappaqua’s most coveted streets, exudes timeless charm while offering modern comforts. Ideally located just minutes from train station and town, with direct sidewalk access for easy walks to the heart of Chappaqua, this meticulously maintained and tastefully updated home, combines the best of both worlds -- generously scaled rooms that

Cindy Glynn 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

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

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.

Exciting and new state-of-the-art expansion and renovation by highly recognized local developer, Tavo Development teaming with noted architect Teo Seguenza. Ready for occupancy in Spring 2026. Meticulous attention to detail, years of experience and master craftsmanship are combined in this new offering, encompassing 5,536 sq ft, 4 bedrooms, 5 full and 2 half baths, a finished walk-out lower level

Brian Milton Compass Greater NY, LLC

Set on 3.25 private acres of lush formal gardens and mature woodlands, this one-of-a-kind Chappaqua residence is a rare architectural treasure. Designed in the 1930s by renowned Westchester architect James Renwick Thomson, the home blends refined sophistication with warm, inviting charm—offering an unparalleled living experience just minutes from the heart of town. From Palladian windows and

Cindy Glynn Compass Greater NY, LLC

Beautifully updated 2-bedroom, 2.5-bath townhouse in the desirable Old Farm Lake community. The open layout features new hardwood floors on the main level, freshly painted interiors, and renovated baths. Upstairs offers two generous bedrooms with ensuite baths, including a primary suite with ample closet space and an updated bath. Relax on your private patio with lake views and enjoy community

Amanda Acard Nestedge Realty

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, cafés, 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

Sari Shaw 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 20 Wallace Way – a rare offering in the sold-out Chappaqua Crossings Carriages community. This sophisticated Byram Wetherby model redefines townhouse living with nearly 3,000 sq. ft. of thoughtfully curated interiors, exceptional finishes, and inviting outdoor spaces. Ideally set along an expansive open lawn, the home enjoys abundant sunlight, privacy, and serene views throughout the

Craig DeCecchis Corcoran Legends Realty

Executive Raised Ranch 4 beds 2 Bath home. Enjoy comfort and sophistication with red oak hardwood flooring, recent upgrades like a new roof, boiler. Large living room with ample space for holiday gatherings. Entertain effortlessly with three freshly stained multi-level decks, perfect for parties and functions. Large yard to enjoy outdoor activities, with three sheds, offers plenty of storage .

Harry Donofrio Town and Village Real Estate

Move right in to this 2-bedroom + loft, 2.5-bathroom townhouse in the highly sought-after Chappaqua School District. Freshly painted throughout and updated with brand-new quartz countertops, new dishwasher and new kitchen flooring, this home offers immediate comfort with the flexibility to personalize. The dining area features sliding doors that open to a grassy green space, while the kitchen

Karin Kimtis Compass Greater NY, LLC

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

All the space and privacy of a single-family home with the ease of condo living! One of the few completely stand-alone and private townhouses in Apple Hill Farm, this spacious 2-bedroom, 2.5-bath home offers a rare blend of comfort, style, and convenience. Enjoy the serene setting from a large wrap-around wood deck overlooking lush, wooded views—perfect for morning coffee or evening entertaining.

Karin Kimtis 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

Major Renovation required.Property being sold As Is. Verify Taxes with municipality. Price includes New Construction and Engineering Plans with Clean Asbestos Abatement Certificate. Underground Oil Tank has been removed with a Clear D.E.C; Certificate.

Joseph Vitulli Elite Properties

Move right into this beautifully updated three bedroom, two bathroom ranch, perfectly situated within the award-winning Chappaqua school district. Thoughtfully renovated from top to bottom, this home offers modern comfort and timeless charm. The heart of the home is the stylish kitchen featuring classic oak cabinetry, sleek quartz countertops, and ample space for cooking and entertaining. Both

Alexander Marks William Raveis-New York LLC

Welcome home to this well-maintained residence in the heart of vibrant Chappaqua! This 4 bedroom and 2.5 full bathroom house is located in the award-winning Chappaqua school district. Step inside to discover gleaming hardwood floors throughout, a cozy living room with a wood-burning fireplace, and a bright, charming dining room. The kitchen features ample cabinetry, granite countertops, and

Thomas Hennerty

Experience the vibrancy and user-friendly vibe of the Hamlet of Chappaqua in this very special move-in ready, end-unit townhouse, which could be the one you’ve been waiting for. Perfectly located, it is walkable to train, schools, restaurants, shops, farmer’s market, town hall, library and more. It offers generous space with flexibility of use featuring two large bedrooms, plus loft, lower level

Nancy Jones Julia B Fee Sothebys Int. Rlty