4,404

Chappaqua, NY Homes

Section Image
  • 7 Oak Hill Rd, Chappaqua, NY 10514

    $1,320,000 Sold Jun 06, 2025

    • 2,628 Sq Ft
    • $502/SF
    • 6 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1968

    7 Oak Hill Rd, Chappaqua, NY 10514

    Welcome to 7 Oak Hill Road, Chappaqua, a spacious and lovingly maintained 4-Bed/3-Bath Raised Ranch set on a flat .67-acre parcel on a neighborly street and buffered by a bird sanctuary. A covered front porch introduces a double-door entry. Large windows front and rear bathe the wide, open living and dining rooms in soft, natural light. Dine casually in the morning-sun-facing breakfast area of

    Stacy Levey William Raveis-New York, LLC

    7 Oak Hill 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

    Danae Richards William Raveis-New York, LLC

    10 Leroy Place, 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
  • 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

    Thomas Jacovino Toll Brothers Real Estate Inc.

    20 Dewitt Dr Unit 72, 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

    Sari Shaw Compass Greater NY, LLC

    25 Random Farms Dr, 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
  • 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
  • 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
  • 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
  • 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

    Thomas Jacovino Toll Brothers Real Estate Inc.

    7 Dewitt Dr Unit 79, 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
  • 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
  • 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
  • 50 Mountain Peak Rd, Chappaqua, NY 10514

    $1,290,000 Sold May 09, 2025

    • 3,229 Sq Ft
    • $400/SF
    • 19 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1968

    50 Mountain Peak Rd, Chappaqua, NY 10514

    Expanded Cape Cod Colonial in Prime Chappaqua Location. Discover the perfect blend of privacy, convenience, and potential in this delightful 4-bedroom, 3-bath home, nestled in a sought-after Chappaqua location. Set on a fabulous private lot, this lovingly maintained property offers a rare opportunity to customize and create your dream home while enjoying modern updates and timeless character. The

    Wendy Nolan Houlihan Lawrence Inc.

    50 Mountain Peak Rd, Chappaqua, NY 10514
  • 150 North Bedford Ro Chappaqua Rd Unit D1, Chappaqua, NY 10514

    $455,000 Sold May 08, 2025

    • 814 Sq Ft
    • $559/SF
    • 44 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1984

    150 North Bedford Ro Chappaqua Rd Unit D1, Chappaqua, NY 10514

    Chappaqua Commons Complex. Location. Location. Location. End-Unit with open floor plan in the heart of Chappaqua! Move right in! Totally renovated and very spacious filled with natural lighting. Impeccable 1 Bedroom with double built-in California closets, 1 updated bath with custom built-in cabinetry and radiant floor heating, modern, updated kitchen with granite countertops and under cabinets

    Alicja Bohmrich Houlihan Lawrence Inc.

    150 North Bedford Ro Chappaqua Rd Unit D1, Chappaqua, NY 10514
  • 150 N Bedford Rd Unit C9, Chappaqua, NY 10514

    $415,000 Sold May 08, 2025

    • 980 Sq Ft
    • $423/SF
    • 16 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1983

    150 N Bedford Rd Unit C9, Chappaqua, NY 10514

    Welcome to effortless in-town living! This ground-floor condo in sought-after Chappaqua Commons offers an unbeatable location adjacent to downtown Chappaqua's charming shops, restaurants, award-winning schools, and convenient public transportation. Floor-to-ceiling windows flood the living area with natural light, complementing brand-new floors & creating a sunny, inviting atmosphere. With

    Jessica Broomhead Compass Greater NY, LLC

    150 N Bedford Rd Unit C9, Chappaqua, NY 10514
  • 12 Highland Ave Unit C, Chappaqua, NY 10514

    $515,000 Sold May 07, 2025

    • 1,387 Sq Ft
    • $371/SF
    • 14 Days On Market
    • 1 Bed
    • 2 Baths
    • Built 1987

    12 Highland Ave Unit C, Chappaqua, NY 10514

    Welcome to 12 Highland Ave, a beautifully updated condo, located in the heart of historic Chappaqua, NY. This move-in-ready home offers the perfect combination of convenience and comfort, just steps from the train station, shops, restaurants, and more.This two-level residence on two levels providing the flexibility to live like a two-bedroom home. The main floor includes a foyer, a bright

    Natalia Wixom Compass Greater NY, LLC

    12 Highland Ave Unit C, Chappaqua, NY 10514
  • 27 Neustadt Ln, Chappaqua, NY 10514

    $2,475,000 Sold May 06, 2025

    • 4,974 Sq Ft
    • $498/SF
    • 8 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1986

    27 Neustadt Ln, Chappaqua, NY 10514

    Nestled on a private, picturesque lot in one of Chappaqua's most sought-after cul de sac neighborhoods, this stunning home offers a unique blend of rustic charm and modern luxury. This meticulous Peter Smith designed residence is reminiscent of a classic barn, with floor to ceiling windows and abundance of natural light, enhanced by brand new Marvin windows. Soaring ceilings, exposed beams, and

    Joanne Milch William Raveis-New York, LLC

    27 Neustadt Ln, Chappaqua, NY 10514
  • 44 Wynnewood Rd, Chappaqua, NY 10514

    $1,150,000 Sold May 06, 2025

    • 1,922 Sq Ft
    • $598/SF
    • 8 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1937

    44 Wynnewood Rd, Chappaqua, NY 10514

    Discover your dream home in Chappaqua! Located less than 1 mile from town and train, yet a tranquil retreat surrounded by mature trees on a quiet road. This light filled cape offers the charm and warmth of the 30's with modern conveniences including a fabulous new kitchen with stainless Bosch appliances. The house features exposed white beamed ceilings and wood floors throughout.The floor

    Barbara Pagliuca Houlihan Lawrence Inc.

    44 Wynnewood Rd, Chappaqua, NY 10514
  • 24 Marcourt Dr, Chappaqua, NY 10514

    $1,620,000 Sold May 05, 2025

    • 2,830 Sq Ft
    • $572/SF
    • 7 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1934

    24 Marcourt Dr, Chappaqua, NY 10514

    Vintage 4-bedroom stone and shingle colonial home showcasing original finishes and modern renovations. This home is located in the Dodge Farms neighborhood of Chappaqua, close to town and the railroad station, situated on 1 level acre of private property with an inground saltwater pool. Inside a traditional floor plan with hardwood floors, the main level with a renovated eat-in kitchen equipped

    Edward Holmes William Raveis-New York, LLC

    24 Marcourt Dr, Chappaqua, NY 10514

Showing Results 241 - 280, Page 7 of 18

New York Westchester County Chappaqua

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group