4,411

Chappaqua, NY Homes

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  • 5 Grove Mews, Chappaqua, NY 10514
    5 Grove Mews, Chappaqua, NY 10514
    5 Grove Mews, Chappaqua, NY 10514
    /24

    $830,000 Open Sat 11AM - 1PM

    • 2 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    5 Grove Mews, Chappaqua, NY 10514

    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

    5 Grove Mews, Chappaqua, NY 10514
  • 24 Greenbriar Dr, Chappaqua, NY 10514

    $1,415,000 Sold Jun 06, 2025

    • 2,781 Sq Ft
    • $509/SF
    • 10 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1978

    24 Greenbriar Dr, Chappaqua, NY 10514

    Nestled on a quiet cul-de-sac street, 24 Greenbriar Drive seamlessly blends quality construction with modern amenities. This beautifully updated and meticulously maintained four-bedroom, three-bathroom home is truly turnkey.The renovated kitchen is perfect for both everyday living and entertaining, featuring a breakfast nook with built-in seating and a sliding glass door that opens to a spacious

    Jennifer Harris Compass Greater NY, LLC

    24 Greenbriar Dr, Chappaqua, NY 10514
  • 31 Wynnewood Rd, Chappaqua, NY 10514
    31 Wynnewood Rd, Chappaqua, NY 10514
    31 Wynnewood Rd, Chappaqua, NY 10514
    /36

    $1,249,000

    • 4 Beds
    • 3 Baths
    • 2,420 Sq Ft

    31 Wynnewood Rd, Chappaqua, NY 10514

    Charming & renovated Colonial set on a quiet street just a few minutes from Chappaqua’s town and train station, effortlessly blends character with thoughtful modern updates. Surrounded by mature trees, professional landscaping with specimen plantings, and flowering perennial gardens, this home offers a truly special outdoor setting with a flat yard, tiered deck, stone patio, and fire pit—perfect

    Cindy Glynn Compass Greater NY, LLC

    31 Wynnewood Rd, Chappaqua, NY 10514
  • 10 Leroy Place, Chappaqua, NY 10514

    $870,000 Sold Jun 04, 2025

    • 1,492 Sq Ft
    • $583/SF
    • 12 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1905

    10 Leroy Place, Chappaqua, NY 10514

    Welcome to your next adventure! This cozy 2-bedroom cottage is nestled on a picturesque piece of land, offering endless potential for those with vision and creativity. Surrounded by nature, this property is perfect for those looking for a peaceful retreat, a weekend getaway, or a renovation project to make their own.Though in need of remodeling, the home provides a solid foundation to bring your

    Danae Richards William Raveis-New York, LLC

    10 Leroy Place, Chappaqua, NY 10514
  • 5 Sutton Farm Dr, Chappaqua, NY 10514
    5 Sutton Farm Dr, Chappaqua, NY 10514
    5 Sutton Farm Dr, Chappaqua, NY 10514
    /47

    $3,699,000

    • 4 Beds
    • 7 Baths
    • 7,708 Sq Ft

    5 Sutton Farm Dr, Chappaqua, NY 10514

    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

    5 Sutton Farm Dr, Chappaqua, NY 10514
  • 33 Kipp St, Chappaqua, NY 10514

    $970,000 Sold May 30, 2025

    • 1,923 Sq Ft
    • $504/SF
    • 11 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1850

    33 Kipp St, Chappaqua, NY 10514

    Welcome to 33 Kipp Street in Chappaqua, a vintage country farmhouse that exudes charm and character. Perched on a picturesque hillside, this three-bedroom home invites you in with its classic rocking chair front porch—a perfect spot to unwind and enjoy the serene surroundings.Spanning 1,923 square feet, the home was lovingly restored in 2011, seamlessly blending historic charm with modern

    Deena Bouchier Compass Greater NY, LLC

    33 Kipp St, Chappaqua, NY 10514
  • 21 Kipp St, Chappaqua, NY 10514
    21 Kipp St, Chappaqua, NY 10514
    21 Kipp St, Chappaqua, NY 10514
    /36

    $1,200,000

    • 4 Beds
    • 2.5 Baths
    • 2,447 Sq Ft

    21 Kipp St, Chappaqua, NY 10514

    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

    21 Kipp St, Chappaqua, NY 10514
  • 20 Dewitt Dr Unit 72, Chappaqua, NY 10514

    $1,558,667 Sold May 30, 2025

    • 2,945 Sq Ft
    • $529/SF
    • 23 Days On Market
    • 2 Beds
    • 3.5 Baths
    • Built 2024

    20 Dewitt Dr Unit 72, Chappaqua, NY 10514

    HOME IS UNDER CONSTRUCTION- READY FOR FALL 2024 CLOSING2 BR Briarcliff Floorplan with primary on first floor. A finished basement with half bath give plenty of room for everyone to enjoy. This outstanding home is located in a great location facing greenspace on one side and forest views from the rooftop deck. It is located in the heart of the neighborhood where you can walk to shopping, cafes,

    Thomas Jacovino Toll Brothers Real Estate Inc.

    20 Dewitt Dr Unit 72, Chappaqua, NY 10514
  • 1008 King St, Chappaqua, NY 10514
    1008 King St, Chappaqua, NY 10514
    /2

    $690,000

    • 1 Bed
    • 1.5 Baths
    • 1,052 Sq Ft

    1008 King St, Chappaqua, NY 10514

    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

    1008 King St, Chappaqua, NY 10514
  • 25 Random Farms Dr, Chappaqua, NY 10514

    $2,300,000 Sold May 29, 2025

    • 4,490 Sq Ft
    • $512/SF
    • 6 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1992

    25 Random Farms Dr, Chappaqua, NY 10514

    Welcome to this sophisticated 4-bedroom Colonial in Random Farms, one of Chappaqua’s most sought-after communities. Designed with an open-flow layout and abundant natural light, this home offers effortless connectivity between spacious living areas—ideal for everyday living, entertaining, and working from home.Recent enhancements include a new roof, solar panels, and upgraded mechanical systems,

    Sari Shaw Compass Greater NY, LLC

    25 Random Farms Dr, Chappaqua, NY 10514
  • 10 Barnes Ln, Chappaqua, NY 10514
    10 Barnes Ln, Chappaqua, NY 10514
    10 Barnes Ln, Chappaqua, NY 10514
    /21

    $1,099,000

    • 3 Beds
    • 2 Baths
    • 1,776 Sq Ft

    10 Barnes Ln, Chappaqua, NY 10514

    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

    10 Barnes Ln, Chappaqua, NY 10514
  • 386 N Greeley Ave Unit 43B, Chappaqua, NY 10514

    $727,500 Sold May 28, 2025

    • 1,660 Sq Ft
    • $438/SF
    • 11 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1984

    386 N Greeley Ave Unit 43B, Chappaqua, NY 10514

    Welcome to 386 N. Greeley Ave, a beautifully renovated, move-in-ready home located in the sought-after Chestnut Oaks community in Chappaqua. This bright and spacious two-bedroom condo offers offers low-maintenance living with the perfect blend of style, comfort, and convenience. Located in the award-winning Chappaqua School District, this sun-filled upper-level unit has been thoughtfully updated

    Rachel Lacoste Houlihan Lawrence Inc.

    386 N Greeley Ave Unit 43B, Chappaqua, NY 10514
  • 380 Whippoorwill Rd, Chappaqua, NY 10514
    380 Whippoorwill Rd, Chappaqua, NY 10514
    380 Whippoorwill Rd, Chappaqua, NY 10514
    /14

    $625,000

    • 3 Beds
    • 2 Baths
    • 880 Sq Ft

    380 Whippoorwill Rd, Chappaqua, NY 10514

    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

    380 Whippoorwill Rd, Chappaqua, NY 10514
  • 395 Bedford Rd, Chappaqua, NY 10514

    $1,589,000 Sold May 28, 2025

    • 3,041 Sq Ft
    • $523/SF
    • 26 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1955

    395 Bedford Rd, Chappaqua, NY 10514

    An impressive and tastefully appointed five bedroom colonial home in the much sought after Chappaqua School District. Set on just over one beautiful acre of level land, this impressive home offers the perfect blend of tranquility and convenience, with easy access to the Chappaqua train station. The heart of the home is the spacious, airy, sun-filled family room, featuring a wall of full length

    Catherine O'Connor Houlihan Lawrence Inc.

    395 Bedford Rd, Chappaqua, NY 10514
  • 816 Hardscrabble Rd, Chappaqua, NY 10514
    816 Hardscrabble Rd, Chappaqua, NY 10514
    816 Hardscrabble Rd, Chappaqua, NY 10514
    /32

    $875,000 Open Sun 2PM - 3:30PM

    • 3 Beds
    • 2 Baths
    • 1,660 Sq Ft

    816 Hardscrabble Rd, Chappaqua, NY 10514

    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

    816 Hardscrabble Rd, Chappaqua, NY 10514
  • 2 South Place, Chappaqua, NY 10514

    $1,450,000 Sold May 22, 2025

    • 2,233 Sq Ft
    • $649/SF
    • 9 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1936

    2 South Place, Chappaqua, NY 10514

    Welcome to 2 South Place - A stylish family home in the desirable Hillholme Community of Chappaqua, within the Chappaqua School District. This residence blends an integration of classic traditional and modern design offering elegant living spaces and a prime location. First level includes a Classic living room with fireplace, recess lighting, formal dinning room, recess lighting. Gourmet

    Toni DiMichelo Houlihan Lawrence Inc.

    2 South Place, Chappaqua, NY 10514
  • 73 S Bedford Rd, Chappaqua, NY 10514
    73 S Bedford Rd, Chappaqua, NY 10514
    73 S Bedford Rd, Chappaqua, NY 10514
    /32

    $849,000

    • 4 Beds
    • 2.5 Baths
    • 1,584 Sq Ft

    73 S Bedford Rd, Chappaqua, NY 10514

    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

    73 S Bedford Rd, Chappaqua, NY 10514
  • 3 Dewitt Dr Unit 77, Chappaqua, NY 10514

    $1,715,408 Sold May 16, 2025

    • 3,269 Sq Ft
    • $525/SF
    • 39 Days On Market
    • 2 Beds
    • 3.5 Baths
    • Built 2024

    3 Dewitt Dr Unit 77, Chappaqua, NY 10514

    HOME IS TO BE BUILT. 2 BR very popular Greeley Floorplan with primary on first floor. We have a model of this home to walk through. It is ideally sized at 3,269 sq. ft. and includes 2 BR + office, huge loft, finished basement with media room and full bath. The 2-story open concept great room and kitchen allow for large family gatherings. The open island with ample seating beckons your inner

    Thomas Jacovino Toll Brothers Real Estate Inc.

    3 Dewitt Dr Unit 77, Chappaqua, NY 10514
  • 29 Meadow Ln, Chappaqua, NY 10514
    29 Meadow Ln, Chappaqua, NY 10514
    29 Meadow Ln, Chappaqua, NY 10514
    /43

    $1,199,000 Open Sat 11:30AM - 1PM

    • 5 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    29 Meadow Ln, Chappaqua, NY 10514

    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

    29 Meadow Ln, Chappaqua, NY 10514
  • 7 Dewitt Dr Unit 79, Chappaqua, NY 10514

    $1,519,995 Sold May 16, 2025

    • 3,614 Sq Ft
    • $421/SF
    • 354 Days On Market
    • 2 Beds
    • 3.5 Baths
    • Built 2025

    7 Dewitt Dr Unit 79, Chappaqua, NY 10514

    HOME ALMOST COMPLETED- SPRING 2025 CLOSE! Byram Farmhouse. Designer features already selected.Home includes a finished basement with full bath, media room and may more upgrades. The open concept great room and kitchen allow for large family gatherings. The open island with ample seating beckons your inner chief to come alive. A roaring fireplace will warm the entire home. A private rooftop

    Thomas Jacovino Toll Brothers Real Estate Inc.

    7 Dewitt Dr Unit 79, Chappaqua, NY 10514
  • 149 King St Unit 4, Chappaqua, NY 10514
    149 King St Unit 4, Chappaqua, NY 10514
    149 King St Unit 4, Chappaqua, NY 10514
    /28

    $829,000 Open Sat 1PM - 3PM

    • 2 Beds
    • 2.5 Baths
    • 1,767 Sq Ft

    149 King St Unit 4, Chappaqua, NY 10514

    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

    149 King St Unit 4, Chappaqua, NY 10514
  • 72 Carolyn Place, Chappaqua, NY 10514

    $3,375,000 Sold May 14, 2025

    • 8,291 Sq Ft
    • $407/SF
    • 140 Days On Market
    • 4 Beds
    • 8 Baths
    • Built 2000

    72 Carolyn Place, Chappaqua, NY 10514

    Elegant and sophisticated, shingle style Colonial sited on 3.46 acres of level, idyllic, private property in one of Chappaqua's most coveted neighborhoods. A private, gated drive introduces this 5 bedroom, 8,000+sq ft home, built by the renowned McKenna Associates, known for quality construction and meticulous workmanship. Designed with luxury finishes and amenities, this home combines both

    Cindy Glynn Compass Greater NY, LLC

    72 Carolyn Place, Chappaqua, NY 10514
  • 200 Millwood Rd, Chappaqua, NY 10514
    200 Millwood Rd, Chappaqua, NY 10514
    200 Millwood Rd, Chappaqua, NY 10514
    /33

    $1,799,999

    • 4 Beds
    • 3 Baths
    • 3,009 Sq Ft

    200 Millwood Rd, Chappaqua, NY 10514

    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

    200 Millwood Rd, Chappaqua, NY 10514
  • 3 Bradley Farms, Chappaqua, NY 10514

    $2,700,000 Sold May 09, 2025

    • 5,947 Sq Ft
    • $454/SF
    • 15 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1947

    3 Bradley Farms, Chappaqua, NY 10514

    Exquisite Bradley Farms Colonial: A Perfect Blend of Timeless Elegance and Modern Comfort. Discover the charm of this beautifully updated home, perfectly positioned on a coveted cul-de-sac. This exceptional residence masterfully combines timeless style with modern amenities, creating an inviting sanctuary for discerning buyers.Step inside to find a thoughtfully designed interior, featuring

    Amrita Singh William Raveis-New York, LLC

    3 Bradley Farms, Chappaqua, NY 10514
  • 249 Mill River Rd, Chappaqua, NY 10514
    249 Mill River Rd, Chappaqua, NY 10514
    249 Mill River Rd, Chappaqua, NY 10514
    /48

    $825,000

    • 4 Beds
    • 2 Baths
    • 2,100 Sq Ft

    249 Mill River Rd, Chappaqua, NY 10514

    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

    249 Mill River Rd, Chappaqua, NY 10514
  • 2 Cedar Ln, Chappaqua, NY 10514

    $2,201,800 Sold May 09, 2025

    • 4,462 Sq Ft
    • $493/SF
    • 35 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1963

    2 Cedar Ln, Chappaqua, NY 10514

    Welcome to 2 Cedar Lane, one of Chappaqua’s most charming and cozy capes situated on a quiet corner close to town. The home boasts over 4,400 square feet of bright and airy space, offering 5 bedrooms and 3/full 1/half bathrooms. The layout is designed for easy living with the primary bedroom + 2 bedrooms on the main floor, 2 bedrooms upstairs, and a finished lower level with ample space for

    Francie Malina Compass Greater NY, LLC

    2 Cedar Ln, Chappaqua, NY 10514

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