4,404

Chappaqua, NY Homes

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  • 42 Seven Bridges Rd, Chappaqua, NY 10514

    $1,890,000 Sold Aug 08, 2025

    • 4,561 Sq Ft
    • $414/SF
    • 7 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1785

    42 Seven Bridges Rd, Chappaqua, NY 10514

    Featured in Westchester magazine’s “Best Places to Live 2016” as an outstanding example of a Federal style colonial residence, this one-of-a-kind classic offers architectural integrity combined w impeccable present day renovations & amenities. This 5BR/3.1Bth colonial offers center hall layout, multiple fireplaces, exposed hand hewn beamed ceilings, post & beam construction in upper level, wide

    Sena Baron William Raveis-New York, LLC

    42 Seven Bridges Rd, Chappaqua, NY 10514
  • 12 Pond Hill Rd, Chappaqua, NY 10514

    $1,445,000 Sold Aug 07, 2025

    • 2,652 Sq Ft
    • $545/SF
    • 5 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1951

    12 Pond Hill Rd, Chappaqua, NY 10514

    Picture perfect Cape on level landscaped property with lush lawns radiates curb appeal. Beautifully updated and impeccably maintained with a blend of classic charm and modern luxury. Light-filled rooms with gleaming hardwood floors enhance the well proportioned living spaces. The renovated eat-in kitchen features white cabinetry, stainless steel appliances, quartz countertops and tasteful

    Jennifer Harris Compass Greater NY, LLC

    12 Pond Hill Rd, Chappaqua, NY 10514
  • 45 Crossways, Chappaqua, NY 10514

    $1,560,000 Sold Aug 07, 2025

    • 2,246 Sq Ft
    • $695/SF
    • 10 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1935

    45 Crossways, Chappaqua, NY 10514

    Storybook 1930’s-era Tudor-style shingle cottage delightfully renovated & updated with all the comforts for the 21st century. Believed to be originally derived from Standard Homes Co. classic Densmore model. A welcoming entry vestibule with French door introduces a wide, front-facing living room, warmed by a stout wood-burning fireplace. Gather together in the dining room to enjoy holiday feasts

    Stacy Levey William Raveis-New York, LLC

    45 Crossways, Chappaqua, NY 10514
  • 101 Hardscrabble Lake Dr, Chappaqua, NY 10514

    $1,800,000 Sold Aug 01, 2025

    • 4,930 Sq Ft
    • $365/SF
    • 38 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1998

    101 Hardscrabble Lake Dr, Chappaqua, NY 10514

    Welcome to this spacious 5 Bedrm Colonial on 1.5+ acres in the sought-after Hardscrabble Lake neighborhood. Step inside and you will be delighted throughout -- by the sweeping double staircase, beautiful light Oak flooring, freshly painted interior and so much more. The formal Dining Room and Living Room/Office are graciously-sized, perfect for entertaining. At the heart of the home is an

    Victoria Miller Compass Greater NY, LLC

    101 Hardscrabble Lake Dr, Chappaqua, NY 10514
  • 324 N Greeley Ave, Chappaqua, NY 10514

    $600,000 Sold Aug 01, 2025

    • 1,608 Sq Ft
    • $373/SF
    • 28 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1988

    324 N Greeley Ave, Chappaqua, NY 10514

    Welcome to this beautifully renovated home in highly sought after Chestnut Oaks, steps from downtown Chappaqua. A rare opportunity to buy this end unit townhouse in the award-winning Chappaqua school district. This bright and spacious two-bedroom townhouse features a loft, its own washer/drier and balcony. Enjoy stress free living with low maintenance and taxes, close to town with a pool and

    Nick Rie K. Fortuna Realty, Inc.

    324 N Greeley Ave, Chappaqua, NY 10514
  • 7 High Point Cir, Chappaqua, NY 10514

    $1,615,000 Sold Aug 01, 2025

    • 4,099 Sq Ft
    • $394/SF
    • 13 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1985

    7 High Point Cir, Chappaqua, NY 10514

    Beautifully positioned at the end of a quiet cul-de-sac, this contemporary home offers style and serenity in a prime Chappaqua location. Designed with today’s lifestyle in mind, the open and airy floor plan features soaring ceilings, floor-to-ceiling windows, and sun-drenched spaces throughout. A beautifully updated modern kitchen flows seamlessly into expansive living and dining areas, ideal for

    Cindy Glynn Compass Greater NY, LLC

    7 High Point Cir, Chappaqua, NY 10514
  • 10 Glen Terrace, Chappaqua, NY 10514

    $1,804,000 Sold Jul 31, 2025

    • 3,219 Sq Ft
    • $560/SF
    • 7 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1972

    10 Glen Terrace, Chappaqua, NY 10514

    Discover the perfect blend of elegance and comfort in this beautifully updated four-bedroom colonial, nestled in the coveted Glen Terrace cul-de-sac. This exceptional home is filled with natural light, enhanced by designer-selected colors, stylish light fixtures, and recessed lighting.The heart of the home is the spacious eat-in kitchen, featuring premium finishes such as Emerald Green

    Brendan Preston Houlihan Lawrence Inc.

    10 Glen Terrace, Chappaqua, NY 10514
  • 26 Hemlock Hills, Chappaqua, NY 10514

    $2,875,000 Sold Jul 31, 2025

    • 7,038 Sq Ft
    • $408/SF
    • 63 Days On Market
    • 5 Beds
    • 6.5 Baths
    • Built 1989

    26 Hemlock Hills, Chappaqua, NY 10514

    Introducing this spectacular country retreat, nestled peacefully on over four and a half acres in the leafy and much loved hamlet of Chappaqua. A glorious heated pool, panoramic patios, and endless lawns for play - offering complete privacy and seclusion, while just minutes from Chappaqua’s vibrant downtown and top-rated schools! At the end of the long scenic drive, an architectural beauty

    Wendy Alper Julia B Fee Sothebys Int. Rlty

    26 Hemlock Hills, Chappaqua, NY 10514
  • 122 Valley View Rd, Chappaqua, NY 10514

    $2,050,000 Sold Jul 31, 2025

    • 3,939 Sq Ft
    • $520/SF
    • 6 Days On Market
    • 6 Beds
    • 3.5 Baths
    • Built 1964

    122 Valley View Rd, Chappaqua, NY 10514

    Ideally located in the coveted Dodge Farms neighborhood, this classic Colonial offers an exceptional combination of space, charm, and functionality. Set on over 1.2 acres of lush, private property, this six-bedroom, 3.5-bath home is perfect for both everyday living and effortless entertaining. Step inside to find a sun-drenched main level featuring a spacious formal living room with a beautiful

    Sari Shaw Compass Greater NY, LLC

    122 Valley View Rd, Chappaqua, NY 10514
  • 2 Woodmill Rd, Chappaqua, NY 10514

    $995,000 Sold Jul 28, 2025

    • 5,227 Sq Ft
    • $190/SF
    • 55 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1900

    2 Woodmill Rd, Chappaqua, NY 10514

    Spacious Turn-of-the-Century Converted Cider Mill – A True One-of-a-Kind Home! Nestled on just over 1 acre of lush property, this sprawling and unique home was once a cider mill and has been beautifully converted into a spacious residence. Boasting 3 working fireplaces and retaining many of its original architectural details, this home exudes character and charm. With hardwood floors, high wood

    Mark Seiden Mark Seiden Real Estate Team

    2 Woodmill Rd, Chappaqua, NY 10514
  • 16 Dewitt Dr Unit 70, Chappaqua, NY 10514

    $1,570,856 Sold Jul 25, 2025

    • 3,269 Sq Ft
    • $481/SF
    • 323 Days On Market
    • 2 Beds
    • 3.5 Baths
    • Built 2025

    16 Dewitt Dr Unit 70, Chappaqua, NY 10514

    New Construction! Move in Summer 2025! Greeley Floorplan with primary on first floor. 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 chief to come alive. A private rooftop

    Thomas Jacovino Toll Brothers Real Estate Inc.

    16 Dewitt Dr Unit 70, Chappaqua, NY 10514
  • 55 Old Lyme Rd, Chappaqua, NY 10514

    $1,605,000 Sold Jul 25, 2025

    • 3,365 Sq Ft
    • $477/SF
    • 4 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1968

    55 Old Lyme Rd, Chappaqua, NY 10514

    Classic center hall colonial with hilltop setting in desirable cul-de-sac neighborhood offering sewer/natural gas, steps from Grafflin Elem school and close to town and train., Set on gorgeous flat park-like acre surrounded by evergreens, towering trees and specimen plantings with stone walls.. Expansive Ipe deck (2012), patio, and screened porch with transom windows and high ceilings. 3

    Sena Baron William Raveis-New York, LLC

    55 Old Lyme Rd, Chappaqua, NY 10514
  • 6 Dewitt Dr Unit 65, Chappaqua, NY 10514

    $1,600,000 Sold Jul 22, 2025

    • 3,353 Sq Ft
    • $477/SF
    • 66 Days On Market
    • 2 Beds
    • 3.5 Baths
    • Built 2025

    6 Dewitt Dr Unit 65, Chappaqua, NY 10514

    As you enter this END UNIT Millwood Elite Fairview, the exquisite foyer presents sweeping views of this home's open-concept floor plan and luxurious finishes. A large center island in the kitchen overlooks the casual dining area. The great room is the perfect setting for relaxation with its cozy fireplace and ample natural light. The appealing primary bedroom suite boasts a lavish bath and ample

    Andrea Martone Houlihan Lawrence Inc.

    6 Dewitt Dr Unit 65, Chappaqua, NY 10514
  • 263 Mill River Rd, Chappaqua, NY 10514

    $1,100,000 Sold Jul 22, 2025

    • 3,444 Sq Ft
    • $319/SF
    • 87 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1987

    263 Mill River Rd, Chappaqua, NY 10514

    Step through the automatic double gates into your private sanctuary, framed by a stately stone wall entrance, a charming blue stone and Belgium block walkway, and elegant wrought iron railings. This breathtaking property is beautifully landscaped with lush flower gardens, expansive emerald lawns, and an array of specimen trees and fruit plants that create a serene, park-like

    Carolina Vinciguerra RE/MAX Town & Country

    263 Mill River Rd, Chappaqua, NY 10514
  • 16 Garey Dr, Chappaqua, NY 10514

    $1,125,000 Sold Jul 21, 2025

    • 1,888 Sq Ft
    • $596/SF
    • 18 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1958

    16 Garey Dr, Chappaqua, NY 10514

    Step into a beautifully refreshed Chappaqua residence. This inviting home boasts stunning wooded views, creating a serene and tranquil atmosphere. The thoughtfully designed layout flows seamlessly, connecting a spacious formal living room, an elegant dining area, and a bright, eat-in kitchen. From the kitchen, step out onto a large deck, perfect for alfresco dining and entertaining amidst the

    Sherry Wiggs Houlihan Lawrence Inc.

    16 Garey Dr, Chappaqua, NY 10514
  • 23 Cross Ridge Rd, Chappaqua, NY 10514

    $1,501,000 Sold Jul 21, 2025

    • 3,525 Sq Ft
    • $426/SF
    • 15 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1961

    23 Cross Ridge Rd, Chappaqua, NY 10514

    Spacious 4 bedroom/ 4 bathroom home that lives like a 5+ bedroom in a coveted Chappaqua neighborhood. Light and bright freshly painted updated home with hardwood floors throughout. The first floor has an entry foyer, powder room, eat-in-kitchen with granite countertops and new stainless steel appliances, living room/ dining room with fireplace and sliding doors to a wrap around deck also

    Pamela Akin Douglas Elliman Real Estate

    23 Cross Ridge Rd, Chappaqua, NY 10514
  • 3 Sunset Dr, Chappaqua, NY 10514

    $1,775,000 Sold Jul 17, 2025

    • 3,587 Sq Ft
    • $495/SF
    • 7 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1969

    3 Sunset Dr, Chappaqua, NY 10514

    Welcome to your beautifully maintained 4-bedroom Colonial at 3 Sunset Drive in the heart of Chappaqua! This charming home boasts 3.5 bathrooms and offers a spacious 3,587 square feet of living space. Step inside to find oak wood flooring throughout and a wood-paneled home office, perfect for working from home. Large windows fill the space with natural light, creating a warm and inviting

    Debra Goldenberg Compass Greater NY, LLC

    3 Sunset Dr, Chappaqua, NY 10514
  • 22 Mountain Peak Rd, Chappaqua, NY 10514

    $1,850,000 Sold Jul 15, 2025

    • 4,419 Sq Ft
    • $419/SF
    • 17 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1972

    22 Mountain Peak Rd, Chappaqua, NY 10514

    Beautiful views welcome you to this updated 5 bedroom Colonial, professionally landscaped and located on a perfect cul de sac close to town and schools! The first floor boasts a gracious formal living room w/ a wood-burning fireplace and formal dining rm featuring a sunny bay window. Chef's eat in kitchen with granite counters, island with seating and sliding glass doors to the deck. The

    Usha Subramaniam Compass Greater NY, LLC

    22 Mountain Peak Rd, Chappaqua, NY 10514
  • 12 Spring Ln, Chappaqua, NY 10514

    $999,999 Sold Jul 14, 2025

    • 2,440 Sq Ft
    • $410/SF
    • 10 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1925

    12 Spring Ln, Chappaqua, NY 10514

    Nestled in the heart of Chappaqua, this enchanting stone and wood colonial is move in ready with updates throughout! This two bedroom two and a half bath residence lives like a three bedroom! Just a short walk to shopping, restaurants, parks, school and the train. Beyond the inviting front porch you will find both comfort and charm. The main floor has beautiful beamed ceilings throughout and a

    Suzanne Sanborn William Raveis Real Estate

    12 Spring Ln, Chappaqua, NY 10514
  • 55 Deepwood Dr, Chappaqua, NY 10514

    $2,315,000 Sold Jul 14, 2025

    • 4,199 Sq Ft
    • $551/SF
    • 13 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1927

    55 Deepwood Dr, Chappaqua, NY 10514

    Set on 1.04 level acres of beautifully landscaped property with vibrant perennial gardens and mature plantings, this impeccably renovated four-bedroom, three-and-a-half-bathroom Center Hall Colonial offers 4,199 square feet of thoughtfully designed living space in one of Chappaqua’s most sought-after neighborhoods. A gracious foyer with a classic sweeping staircase welcomes you into the home.

    Avital Soldatenko Houlihan Lawrence Inc.

    55 Deepwood Dr, Chappaqua, NY 10514

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