4,382

Chappaqua, NY Homes

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  • 8 Turtleback Way, Chappaqua, NY 10514
    8 Turtleback Way, Chappaqua, NY 10514
    8 Turtleback Way, Chappaqua, NY 10514
    /50

    $2,485,000 Open Sat 1PM - 3PM

    • 5 Beds
    • 4.5 Baths
    • 6,649 Sq Ft

    8 Turtleback Way, Chappaqua, NY 10514

    Introducing a luxurious lifestyle at 8 Turtleback Way in the prestigious Hardscrabble Lake Community of Chappaqua. This private neighborhood graced with delightful lakes is perfect for peaceful strolls and getting in your daily steps. It also offers the convenience of door-to-door school bus service within the top-rated Chappaqua School District. Nestled on a magnificent 1.24-acre lot, this 6,649

    Michele Iasich-Pagnotta Houlihan & O'Malley R. E. Serv

    8 Turtleback Way, Chappaqua, NY 10514
  • 26 Dewitt Dr Unit 75, Chappaqua, NY 10514

    $1,631,110 Sold Feb 25, 2025

    • 3,335 Sq Ft
    • $489/SF
    • 5 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2024

    26 Dewitt Dr Unit 75, Chappaqua, NY 10514

    HOME NOT COMPLETED YET- 3 BR Millwood Elite home. This outstanding home is located in the heart of the neighborhood where you can walk to shopping, cafe, gym, pool and more. Includes 3 BR + 2 offices, loft and outdoor terrace w built in grill and linear fireplace and interior wet bar in loft. The open concept great room and kitchen allow for large family gatherings. The open island with

    Thomas Jacovino Toll Brothers Real Estate Inc.

    26 Dewitt Dr Unit 75, Chappaqua, NY 10514
  • 21 Wallace Way, Chappaqua, NY 10514
    21 Wallace Way, Chappaqua, NY 10514
    21 Wallace Way, Chappaqua, NY 10514
    /44

    $1,840,000

    • 3 Beds
    • 3.5 Baths
    • 3,614 Sq Ft

    21 Wallace Way, Chappaqua, NY 10514

    Better than new at Chappaqua Crossings Carriages! Be among the first to experience this spectacular new community featuring a delightful and charming village atmosphere in the heart of Westchester, Chappaqua, NY. This stunning “Byram Newhaven model” situated in a prime location within the community, offers great curb appeal with its expansive front porch, stone walls and specimen plantings; and

    Kimberly Renzi Redfin Real Estate

    21 Wallace Way, Chappaqua, NY 10514
  • 39 Barnes Ln, Chappaqua, NY 10514

    $425,000 Sold Feb 25, 2025

    • Land
    • 1.06 Acres
    • $400,943 per Acre
    • 87 Days On Market

    39 Barnes Ln, Chappaqua, NY 10514

    ATTENTION BUILDERS! GRAB YOUR HARD HATS! Build your dream home on a desirable cul de sac street in Chappaqua School District! 4 bedroom septic approved! Reach out today for more information!

    Sari Shaw Compass Greater NY, LLC

    39 Barnes Ln, Chappaqua, NY 10514
  • 5 Crossways, Chappaqua, NY 10514
    5 Crossways, Chappaqua, NY 10514
    5 Crossways, Chappaqua, NY 10514
    /22

    $1,099,000

    • 4 Beds
    • 2.5 Baths
    • 2,212 Sq Ft

    5 Crossways, Chappaqua, NY 10514

    Move right into this walk-to-town beautifully updated 4-bedroom, 2.5-bath Colonial that offers the perfect balance of classic charm and modern convenience. Just steps from the heart of Chappaqua, this home features an open-concept layout and flexible spaces ideal for everyday living and effortless entertaining.Step through the storybook Dutch door to a light-filled, double-height entry with a

    Jill Urban Compass Greater NY, LLC

    5 Crossways, Chappaqua, NY 10514
  • 4 Timberland Pass, Chappaqua, NY 10514

    $595,000 Sold Feb 21, 2025

    • 1,550 Sq Ft
    • $384/SF
    • 34 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1979

    4 Timberland Pass, Chappaqua, NY 10514

    This home is located in Apple Hill Farm community in Chappaqua NY. This End unit Townhome is located on nice lot with large side and rear property & plenty of privacy. Lots of light with windows galore. This home features 2 bedrooms, with 2.5 baths. A huge living room with cathedral ceilings, a wood burning fireplace and lots of windows. Large formal dining room with sliders to a private patio

    Dorothy Botsoe Dorothy Jensen Realty, Inc.

    4 Timberland Pass, Chappaqua, NY 10514
  • 326 Millwood Rd, Chappaqua, NY 10514
    326 Millwood Rd, Chappaqua, NY 10514
    326 Millwood Rd, Chappaqua, NY 10514
    /35

    $1,149,000

    • 3 Beds
    • 3.5 Baths
    • 2,313 Sq Ft

    326 Millwood Rd, Chappaqua, NY 10514

    Welcome to this enchanting, character and light-filled Colonial, nestled on beautiful grounds in the sought-after Chappaqua school district. This gracious home blends timeless character with modern updates, featuring a WOW chef’s kitchen with stainless appliances, a travertine countertops, that has been proudly showcased in Old House Journal magazine. Thoughtfully designed for both everyday

    Cindy Glynn Compass Greater NY, LLC

    326 Millwood Rd, Chappaqua, NY 10514
  • 7 Deer Run Unit 7, Chappaqua, NY 10514

    $750,000 Sold Feb 18, 2025

    • 1,549 Sq Ft
    • $484/SF
    • 27 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1986

    7 Deer Run Unit 7, Chappaqua, NY 10514

    Step into luxury - in this fully renovated condo in Chappaqua at Old Farm Lake development, close to town, train, shops and schools. Enter the foyer with marble floors, leading to the kitchen with Bosch stainless appliances and walk out to front patio. The dining room opens to a spacious living room with a vaulted high ceiling with skylights and decorated with hardwood, complete with a stunning

    Natalia Wixom Compass Greater NY, LLC

    7 Deer Run Unit 7, Chappaqua, NY 10514
  • 35 Ivy Hill Rd, Chappaqua, NY 10514
    35 Ivy Hill Rd, Chappaqua, NY 10514
    35 Ivy Hill Rd, Chappaqua, NY 10514
    /31

    $2,888,000

    • 5 Beds
    • 4.5 Baths
    • 4,004 Sq Ft

    35 Ivy Hill Rd, Chappaqua, NY 10514

    Arise to astonishing sunrises in this gorgeous, modern farmhouse privately set on 2.75 estate-like acres at the end of a cul-de-sac in prestigious Lawrence Farms East. Newly rebuilt in 2020 and further refined since. Grand, two-story entry foyer introduces open floor plan for today’s contemporary living style. Inviting living/dining area with large, front-facing windows, wood-burning fireplace,

    Stacy Levey William Raveis-New York, LLC

    35 Ivy Hill Rd, Chappaqua, NY 10514
  • 40 Aldridge Rd, Chappaqua, NY 10514

    $1,955,000 Sold Feb 04, 2025

    • 3,541 Sq Ft
    • $552/SF
    • 8 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1955

    40 Aldridge Rd, Chappaqua, NY 10514

    Move right in to this beautiful home perfectly situated on a tranquil cul-de-sac, offering the best of both worlds: a spacious, private retreat with the convenience of being close to town and train. This airy & bright 4-bedroom, 4-bathroom home is designed for both comfort & elegance. Discover a first-floor primary bedroom with soaring ceilings & a generous walk-in closet. The heart of the home

    Jodi Greebel Compass Greater NY, LLC

    40 Aldridge Rd, Chappaqua, NY 10514
  • 263 Mill River Rd, Chappaqua, NY 10514
    263 Mill River Rd, Chappaqua, NY 10514
    263 Mill River Rd, Chappaqua, NY 10514
    /46

    $1,150,000 Open Sat 10AM - 12PM

    • 4 Beds
    • 4 Baths
    • 3,444 Sq Ft

    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 setting.Located just

    Carolina Vinciguerra RE/MAX Town & Country

    263 Mill River Rd, Chappaqua, NY 10514
  • 55 Florence Dr, Chappaqua, NY 10514

    $2,275,000 Sold Jan 31, 2025

    • 2,984 Sq Ft
    • $762/SF
    • 4 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1978

    55 Florence Dr, Chappaqua, NY 10514

    Spectacular Mid-Century modern completely renovated and privately set on 2.23 gorgeous park-like acres at the end of a neighborhood cul-de-sac featuring stone walls, professional landscaping, perennial& vegetable gardens, specimen plantings & towering old growth trees for complete privacy, yet close to all. Expansive deck, soaring ceilings throughout, open plan, walls of glass & abundant natural

    Sena Baron William Raveis-New York, LLC

    55 Florence Dr, Chappaqua, NY 10514
  • 23 Round Hill Rd, Chappaqua, NY 10514
    23 Round Hill Rd, Chappaqua, NY 10514
    23 Round Hill Rd, Chappaqua, NY 10514
    /37

    $1,375,000

    • 5 Beds
    • 3.5 Baths
    • 3,230 Sq Ft

    23 Round Hill Rd, Chappaqua, NY 10514

    Welcome to 23 Round Hill Road, a picture-perfect, timeless, Center Hall Colonial on a premier street just minutes from Chappaqua schools, train station, & a variety of restaurants, shops & grocery stores (including Whole Foods & Starbucks), a prime location for convenience & lifestyle. Set on a beautifully landscaped property, this home exudes classic appeal. As you step through double front

    Michael Levy eXp Realty

    23 Round Hill Rd, Chappaqua, NY 10514
  • 32 Begg Dr, Chappaqua, NY 10514

    $999,999 Sold Jan 30, 2025

    • 1,657 Sq Ft
    • $603/SF
    • 20 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1927

    32 Begg Dr, Chappaqua, NY 10514

    Step into the timeless charm of this captivating colonial located on a sought-after tree-lined cul-de-sac. This move-in-ready home offers an open floor plan with abundant windows, creating a bright and welcoming atmosphere. The stunning living room/great room features a fireplace, elegant columns, detailed moldings, recessed lighting, and walls of windows, flooding the space with natural light.

    Wendy Nolan Houlihan Lawrence Inc.

    32 Begg Dr, Chappaqua, NY 10514
  • 101 Hardscrabble Lake Dr, Chappaqua, NY 10514
    101 Hardscrabble Lake Dr, Chappaqua, NY 10514
    101 Hardscrabble Lake Dr, Chappaqua, NY 10514
    /33

    $1,799,000

    • 5 Beds
    • 3.5 Baths
    • 4,930 Sq Ft

    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
  • 33 Chatham Rd, Chappaqua, NY 10514

    $1,175,000 Sold Jan 24, 2025

    • 2,100 Sq Ft
    • $560/SF
    • 18 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1942

    33 Chatham Rd, Chappaqua, NY 10514

    Beautifully renovated home 3 bedroom 2.5 bath on 1.3 acres in Chappaqua Ridge community. With its classic center hall colonial layout and beautiful renovations, it's perfect for someone looking for both charm and modern updates. New kitchen with deck overlooking private yard Is ideal for entertaining, oversized Livingroom with wood burning fireplace, formal Dining Room, Primary suite , along

    Phyllis Lerner Corcoran Legends Realty

    33 Chatham Rd, 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 gut renovated, offering the perfect blend of modern comfort and timeless character. Thoughtfully redesigned from top to bottom, this home is the ideal retreat—whether you're looking for a weekend getaway or a full-time residence. Located just minutes from the heart of downtown Chappaqua and mere seconds from Chappaqua Crossing and Horace Greeley High

    Sari Shaw Compass Greater NY, LLC

    380 Whippoorwill Rd, Chappaqua, NY 10514
  • 140 S Bedford Rd, Chappaqua, NY 10514

    $1,550,000 Sold Jan 23, 2025

    • 3,631 Sq Ft
    • $427/SF
    • 17 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2004

    140 S Bedford Rd, Chappaqua, NY 10514

    Modern Colonial, nestled on a private 1.23 acre lot in the Chappaqua School District. This 4 bedroom, 3,631 sq ft open flow, expansive home is thoughtfully crafted, featuring generously sized light-filled rooms with large windows and essential amenities. A double height entry foyer with chandelier opens to formal spaces, an office/guest room, formal dining and living rooms. This comfortable, open

    Cindy Glynn Compass Greater NY, LLC

    140 S Bedford Rd, Chappaqua, NY 10514
  • 8 Elizabeth St, Chappaqua, NY 10514
    8 Elizabeth St, Chappaqua, NY 10514
    8 Elizabeth St, Chappaqua, NY 10514
    /33

    $999,000

    • 3 Beds
    • 2.5 Baths
    • 1,824 Sq Ft

    8 Elizabeth St, Chappaqua, NY 10514

    Welcome to 8 Elizabeth Street – A Charming, Turnkey Colonial nestled on a quiet cul-de-sac street. A beautifully updated three-bedroom, two-and-a-half-bathroom Colonial that seamlessly blends style, comfort, and convenience. Step inside to discover a thoughtfully designed layout, where large, updated windows flood the home with natural light. The spacious living room is an inviting gathering

    Jennifer Harris Compass Greater NY, LLC

    8 Elizabeth St, Chappaqua, NY 10514
  • 41 Lila Ln Unit 60, Chappaqua, NY 10514

    $1,624,375 Sold Jan 21, 2025

    • 3,101 Sq Ft
    • $524/SF
    • 117 Days On Market
    • 2 Beds
    • 3.5 Baths
    • Built 2023

    41 Lila Ln Unit 60, Chappaqua, NY 10514

    CONSTRUCTION TO BEGIN SOON ON THIS HOME:2 BR Greeley Floorplan with primary on first floor. An elevator is included as well as a finished basement with full bath, wet bar in 2nd floor loft and open railings to lower level, car charger and teak pavers on the terrace. This outstanding home is located in a private area of the community but still allows owners to walk to shopping,

    Thomas Jacovino Toll Brothers Real Estate Inc.

    41 Lila Ln Unit 60, Chappaqua, NY 10514
  • 260 Mill River Rd, Chappaqua, NY 10514
    260 Mill River Rd, Chappaqua, NY 10514
    260 Mill River Rd, Chappaqua, NY 10514
    /23

    $1,725,000

    • 4 Beds
    • 4.5 Baths
    • 3,561 Sq Ft

    260 Mill River Rd, Chappaqua, NY 10514

    Discover the perfect townhouse alternative or an ideal first home just north of NYC! Nestled on Mill River Road, this inviting 4-bedroom residence offers the best of both worlds—walking distance to the charming town of Chappaqua, with its shops, restaurants, and train station, while benefiting from the highly regarded Pleasantville schools. Commuting is a breeze with the Chappaqua train station

    Sari Shaw Compass Greater NY, LLC

    260 Mill River Rd, Chappaqua, NY 10514
  • 14 Alta Ln, Chappaqua, NY 10514

    $1,600,000 Sold Jan 21, 2025

    • 5,111 Sq Ft
    • $313/SF
    • 48 Days On Market
    • 5 Beds
    • 6 Baths
    • Built 1979

    14 Alta Ln, Chappaqua, NY 10514

    Mid-century modern home lovers will appreciate this 1979 contemporary, designed by Chappaqua architect, Charles Napoli as an homage to Frank Lloyd Wright. Set on 1.35 acres, this 5 BR, 5.1 BA home has walls of windows showcasing the lush property and mature trees. The open plan of the house flows naturally with a grand, open living rm to dining and eat-in kitchen w/ sliders to patio. The great

    Stacey Rechler Douglas Elliman Real Estate

    14 Alta Ln, Chappaqua, NY 10514
  • 26 Hemlock Hills, Chappaqua, NY 10514
    26 Hemlock Hills, Chappaqua, NY 10514
    26 Hemlock Hills, Chappaqua, NY 10514
    /38

    $2,950,000

    • 5 Beds
    • 6.5 Baths
    • 7,038 Sq Ft

    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
  • 54 Spring Rd, Chappaqua, NY 10514

    $1,150,000 Sold Jan 15, 2025

    • 2,482 Sq Ft
    • $463/SF
    • 41 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1935

    54 Spring Rd, Chappaqua, NY 10514

    Set on a quiet street just a few minutes from Chappaqua town center, this charming colonial with effortlessly blends historical character with modern updates. The home showcases original arts & crafts and architectural features - exposed beams, wood trim, and beautifully refinished hardwood floors throughout. Handmade Motawi tiles adorn fireplace. The high-end kitchen, with custom Bilotta

    Natalia Wixom Compass Greater NY, LLC

    54 Spring Rd, Chappaqua, NY 10514
  • 0 Gray Rock Ln Unit KEY828030, Chappaqua, NY 10514
    0 Gray Rock Ln Unit KEY828030, Chappaqua, NY 10514
    0 Gray Rock Ln Unit KEY828030, Chappaqua, NY 10514
    /28

    $1,849,999

    • 4 Beds
    • 2.5 Baths
    • 4,500 Sq Ft

    0 Gray Rock Ln Unit KEY828030, Chappaqua, NY 10514

    Custom design your dream home in a seamless process with ZappiCo, Westchester County's premier Real Estate Developer! This luxurious home is to-be-built in the highly desirable Chappaqua school district. With 4 spacious bedrooms and 2.5 beautifully appointed bathrooms, this home will be meticulously crafted with the finest materials and attention to detail. As you enter, you will be greeted by an

    Mary Ann Tighe Houlihan Lawrence Inc.

    0 Gray Rock Ln Unit KEY828030, Chappaqua, NY 10514
  • 3 High Point Cir, Chappaqua, NY 10514

    $1,700,214 Sold Jan 10, 2025

    • 3,421 Sq Ft
    • $497/SF
    • 9 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1955

    3 High Point Cir, Chappaqua, NY 10514

    Welcome to 3 High Point Circle! This delightful home features 4 spacious bedrooms + 3.5 bathrooms, all set on a beautifully landscaped, fenced-in, 1-acre lot on a sought after cul-de-sac. Inside, you'll love the open floor plan, perfect for entertaining and the spacious family room for relaxation. The Primary suite boasts a newly renovated bathroom and a spacious walk-in closet. The lower level

    Debra Goldenberg Compass Greater NY, LLC

    3 High Point Cir, Chappaqua, NY 10514

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