Chappaqua, NY Houses for Sale

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

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

Welcome to 90 Prospect Drive, a timeless Dutch Colonial nestled on over an acre of picturesque, park-like land in the heart of Chappaqua’s walkable village center. Just a 7-minute stroll to town, train, restaurants, shops, and parks, and only a 5-minute drive to Whole Foods and Life Time Fitness, this rare in-town gem also sits in one of Westchester’s most sought-after school districts. Set back

Stacy Levey William Raveis-New York, LLC

Stately and Inviting, with a rocking chair front porch, this beautifully landscaped Post-Modern Colonial sitting on .73 acres is up for sale in the highly sought-after Random Farms Community. On a lush, level property framed with shade trees, this extraordinary house is beautifully designed and laid out. Enter this 5-bedroom 4.5 bath wonder through a light-filled double height foyer featuring

Alicja Bohmrich Houlihan Lawrence Inc.

Discover the most private home in the prestigious Random Farms community of Chappaqua, NY. Tucked away amid lush, mature landscaping, this stunning five-bedroom contemporary colonial offers a rare sense of natural seclusion and tranquility. Enjoy the ultimate in privacy without sacrificing convenience—just a short stroll to the neighborhood pool, clubhouse, and tennis courts. This exceptional

Suzan Zeolla Houlihan Lawrence Inc.

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

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

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

Step into this beautifully updated 4-bedroom, 2.5-bathroom home, just a short stroll from the vibrant shops, dining, and charm of downtown Chappaqua. Perfectly situated for an easy city commute, this home offers the ideal blend of convenience and tranquility. Inside, you'll find generously sized rooms filled with natural light. The serene primary suite provides a peaceful retreat at the end of

Vanessa Catalano Julia B Fee Sothebys Int. Rlty

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

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

Chappaqua Gem—Welcome to 816 Hardscrabble Road located in a Top-Rated School District!Discover your opportunity to live in the coveted Chappaqua School District with this charming 3-bedroom, 2-bath Split-Level Ranch, nestled on a tranquil half acre lot.This home features a spacious Primary En-Suite, offering comfort and privacy. Recent upgrades include Roof, Liters & Gutters

Daniel Berger RE/MAX Prestige Properties

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

Location, Location, Location. Welcome to the sought-after hamlet of Chappaqua! 29 Meadow Lane is nestled on a charming Cul-De-Sac in a quiet and beautiful neighborhood, this lovely home sitting on over a half-acre offers the perfect blend of comfort, elegance, and versatility. The open concept main floor features a spacious sun-lit dining area, kitchen, living room and sunroom. With 4 bedrooms

Daniel Berger RE/MAX Prestige Properties

Contemporary bi-level 4 beds 2 Bath home. Enjoy comfort and sophistication with red oak hardwood flooring, recent upgrades like a new roof, boiler, and sanitary system. 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

Harry Donofrio Town and Village Real Estate

Fabulous 3 Bedroom Home which lives like 4 Bedroom on rare and lovely cul-de-sac within a 5-minute walk to the nationally ranked Horace Greeley High School, part of the award-winning Chappaqua School District, and to Chappaqua Crossing with its charming shops and restaurants, including Whole Foods, Life Time Gym, Starbucks, and the Chappaqua Performing Arts Center. It is also in close proximity

Wendy Nolan Houlihan Lawrence Inc.

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 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.

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 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

Live minutes from the heart of Chappaqua! Commuters dream to live in this charming tudor-style home near all everyday amenities. Nestled on 1.11 acres, with 3-bedrooms and 2 bathrooms, this fully renovated residence offers timeless character and thoughtful updates throughout. The main level features an inviting entry foyer, a chef’s eat-in kitchen equipped with a gas oven/range, microwave, and

Christine Ricci Keller Williams NY Realty

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.

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