Chappaqua, NY Homes

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  /44

  $1,599,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 2,906 Sq Ft

  20 Wallace Way, Chappaqua, NY 10514

  Welcome to 20 Wallace Way – a rare offering in the sold-out Chappaqua Crossings Carriages community. This sophisticated Byram Wetherby model redefines townhouse living with nearly 3,000 sq. ft. of thoughtfully curated interiors, exceptional finishes, and inviting outdoor spaces. Ideally set along an expansive open lawn, the home enjoys abundant sunlight, privacy, and serene views throughout the

  Craig DeCecchis Corcoran Legends Realty

  20 Wallace Way, Chappaqua, NY 10514
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  $1,465,000 Sold Oct 01, 2025

  • 1,917 Sq Ft
  • $764/SF
  • 11 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1938

  33 High Way, Chappaqua, NY 10514

  Picture-perfect Colonial in Chappaqua's highly sought after Lawrence Farms South neighborhood. Beautifully updated and impeccably maintained 3-bedroom, 3.5-bath home sits on nearly an acre of level, landscaped property with lush lawns and unparalleled curb appeal. Radiating a perfect blend of classic charm and modern luxury, this home welcomes you with light-filled, well-proportioned living

  Jennifer Harris Compass Greater NY, LLC

  33 High Way, Chappaqua, NY 10514
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  Est $2,166,863 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 5,668 Sq Ft

  345 Roaring Brook Rd, Chappaqua, NY 10514

  345 Roaring Brook Rd, Chappaqua, NY 10514
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  /32

  $1,299,500 Pending

  • 3 Beds
  • 3.5 Baths
  • 2,866 Sq Ft

  36 Pond Hill Rd, Chappaqua, NY 10514

  Set on a quiet cul-de-sac, this charming 3-bedroom Cape, which could live like a 4-bedroom, offers the perfect blend of comfort, convenience, and style. The home has been impeccably maintained and thoughtfully renovated, with updates that make it truly move-in ready.From the moment you arrive, the curb appeal stands out, enhanced by updated landscaping and a freshly painted exterior. Inside,

  Danae Richards William Raveis-New York, LLC

  36 Pond Hill Rd, Chappaqua, NY 10514
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  $1,375,000 Sold Oct 01, 2025

  • 2,195 Sq Ft
  • $626/SF
  • 8 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1937

  4 Oak Hill Rd, Chappaqua, NY 10514

  Enjoy easy living in this fully renovated Cape Cod style home situated on a park-like, flat property. Located walking distance to town and train, this 3 bedroom/2.5 bathroom residence offers modern luxuries in a classic country-feeling home. Enter this home through an inviting foyer flanked by a front-to-back living room, featuring a wood-burning fireplace and a formal dining

  Allison Tintenfass Compass Greater NY, LLC

  4 Oak Hill Rd, Chappaqua, NY 10514
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  Est $2,274,251 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 5,534 Sq Ft

  15 Kerry Ln, Chappaqua, NY 10514

  15 Kerry Ln, Chappaqua, NY 10514
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  /47

  $3,499,000 Pending

  • 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
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  $1,730,000 Sold Sep 30, 2025

  • 3,614 Sq Ft
  • $479/SF
  • 110 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2023

  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

  Ken Wile Redfin Real Estate

  21 Wallace Way, Chappaqua, NY 10514
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  Est $2,059,236 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,541 Sq Ft

  28 McKesson Hill Rd, Chappaqua, NY 10514

  28 McKesson Hill Rd, Chappaqua, NY 10514
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  /38

  $3,150,000 Pending

  • 5 Beds
  • 9 Baths
  • 8,775 Sq Ft

  70 Haights Cross Rd, Chappaqua, NY 10514

  Welcome to 70 Haights Cross, an architectural masterpiece in one of Chappaqua’s most coveted neighborhoods. Designed by acclaimed architect Tasos Kokoris, this turn-key 5-bedroom, 7.2-bath colonial blends timeless elegance with today’s most sought-after amenities. Nestled on over two acres of private, professionally landscaped grounds, the property showcases a resort-like setting with a

  Wendy Nolan Houlihan Lawrence Inc.

  70 Haights Cross Rd, Chappaqua, NY 10514
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  $1,747,995 Sold Sep 19, 2025

  • 3,269 Sq Ft
  • $535/SF
  • 235 Days On Market

  • 2 Beds
  • 3.5 Baths
  • Built 2024

  2 Carriage Ln Unit 81, 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.

  2 Carriage Ln Unit 81, Chappaqua, NY 10514
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  Est $1,769,929 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,164 Sq Ft

  1 Round Hill Rd, Chappaqua, NY 10514

  1 Round Hill Rd, Chappaqua, NY 10514
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  /25

  $745,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,244 Sq Ft

  30 Rambling Brook Rd, Chappaqua, NY 10514

  Beautifully updated 2-bedroom, 2.5-bath townhouse in the desirable Old Farm Lake community. The open layout features new hardwood floors on the main level, freshly painted interiors, and renovated baths. Upstairs offers two generous bedrooms with ensuite baths, including a primary suite with ample closet space and an updated bath. Relax on your private patio with lake views and enjoy community

  Amanda Acard Nestedge Realty

  30 Rambling Brook Rd, Chappaqua, NY 10514
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  $1,165,000 Sold Sep 19, 2025

  • 3,728 Sq Ft
  • $312/SF
  • 59 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1965

  57 Hamilton Dr, Chappaqua, NY 10514

  Welcome to a sleek contemporary home that seamlessly blends indoor comfort with an exceptional outdoor retreat. From the moment you enter, you'll appreciate the design's focus on chic, easy living, bathed in natural light and showcasing exposed beams, custom built-ins, and premium appointments. This home boasts an open concept and has been fully updated, living generously like a 4 or 5-bedroom

  Sherry Wiggs Houlihan Lawrence Inc.

  57 Hamilton Dr, Chappaqua, NY 10514
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  Est $2,019,931 Not Listed For Sale

  • 4 Beds
  • 6 Baths
  • 5,474 Sq Ft

  2 Sunset Dr, Chappaqua, NY 10514

  2 Sunset Dr, Chappaqua, NY 10514
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  /21

  $1,299,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,034 Sq Ft

  41 Valley Ln, Chappaqua, NY 10514

  AO as of 9/29. Beautifully sited on a lovely & picturesque acre plus of perfectly flat property on a highly desirable street in the Chappaqua school district, this gracious colonial lives like a four bedroom home. The first floor boasts a formal dining room and living room with oversized windows, a combination eat in kitchen (renovated 2019) and family room with a wood burning fireplace and

  Amanda Goldberg William Raveis-New York, LLC

  41 Valley Ln, Chappaqua, NY 10514
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  $1,679,000 Sold Sep 18, 2025

  • 3,269 Sq Ft
  • $514/SF
  • 137 Days On Market

  • 2 Beds
  • 3.5 Baths
  • Built 2025

  10 Carriage Ln Unit 85, Chappaqua, NY 10514

  Home Under construction! Move-in by Summer 2025' 3269 square feet ! As you enter the Greeley Newhaven, the exquisite foyer presents sweeping views of this home's open-concept floor plan and luxurious finishes. The spacious kitchen and great room provide the ideal space for entertaining. The casual dining area provides the perfect space for entertaining guests with easy access to the kitchen. The

  Andrea Martone Houlihan Lawrence Inc.

  10 Carriage Ln Unit 85, Chappaqua, NY 10514
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  Est $1,561,342 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,029 Sq Ft

  636 Quaker Rd, Chappaqua, NY 10514

  636 Quaker Rd, Chappaqua, NY 10514
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  /23

  $1,325,000 Pending

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

  260 Mill River Rd, Chappaqua, NY 10514

  This sophisticated four-bedroom residence offers an ideal blend of convenience and tranquility just north of New York City. Enjoy the ease of walking to the vibrant village of Chappaqua—with its boutiques, cafés, and train station—while benefiting from the highly regarded Pleasantville School District. Commuting is effortless with the Chappaqua station mere minutes away and seamless access

  Sari Shaw Compass Greater NY, LLC

  260 Mill River Rd, Chappaqua, NY 10514
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  $1,479,320 Sold Sep 17, 2025

  • 2,503 Sq Ft
  • $591/SF
  • 183 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2024

  14 Carriage Ln Unit 87, Chappaqua, NY 10514

  HOME IS UNDER CONSTRUCTION- READY FOR Summer 2025 closing 2 BR Briarcliff Floorplan with primary on first floor. You can still add structural and design features to this home. 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.

  14 Carriage Ln Unit 87, Chappaqua, NY 10514
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  Est $1,224,377 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,022 Sq Ft

  610 Quaker Rd, Chappaqua, NY 10514

  610 Quaker Rd, Chappaqua, NY 10514
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  /40

  $1,159,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,060 Sq Ft

  26 Kings Ct, Chappaqua, NY 10514

  Welcome to 26 Kings Court, Chappaqua, a storybook, village Colonial enchantingly set among towering trees on a quiet cul-de-sac just a short stroll to schools, shops, town and train. If your Brooklyn brownstone could move to the suburbs, this would be it. Regal, barrel-vaulted front portico. Welcoming front entry. French doors introduce the gracious front-facing living room warmed by morning sun

  Stacy Levey William Raveis-New York, LLC

  26 Kings Ct, Chappaqua, NY 10514
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  $1,530,000 Sold Sep 12, 2025

  • 2,420 Sq Ft
  • $632/SF
  • 9 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1928

  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
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  Est $1,527,520 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,032 Sq Ft

  15 Suzanne Ln, Chappaqua, NY 10514

  15 Suzanne Ln, Chappaqua, NY 10514
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  /47

  $3,199,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 6,542 Sq Ft

  93 Haights Cross Rd, Chappaqua, NY 10514

  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

  93 Haights Cross Rd, Chappaqua, NY 10514
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  $1,250,023 Sold Sep 12, 2025

  • 2,000 Sq Ft
  • $625/SF
  • 27 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1934

  29 Begg Dr, Chappaqua, NY 10514

  Welcome to 29 Begg Drive, a meticulously-maintained gem in Chappaqua! This serene property features an open floor plan with hardwood floors, charming traditional architectural features, and numerous upgrades. The sunlit first floor features a kitchen with a large picture window, a living room area, and a dining area. An attached screened-in porch, which overlooks the yard and connects to a large

  Wendy Nolan Houlihan Lawrence Inc.

  29 Begg Dr, Chappaqua, NY 10514
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  Est $1,265,152 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,872 Sq Ft

  619 Quaker Rd, Chappaqua, NY 10514

  619 Quaker Rd, Chappaqua, NY 10514
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  /27

  $1,150,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,264 Sq Ft

  569 Millwood Rd, Chappaqua, NY 10514

  A dramatic and stunning four-bedroom Contemporary home set on 1.2 professionally landscaped acres, designed by Jan Johnsen, former landscape architect for the New York Botanical Gardens. Surrounded by wooded privacy, this serene setting features two separate decks and a ground-level patio that surrounds the exterior of the home. Inside, this home offers a light-filled, modern, and open layout

  Edward Holmes William Raveis-New York, LLC

  569 Millwood Rd, Chappaqua, NY 10514
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  $1,659,995 Sold Sep 10, 2025

  • 3,432 Sq Ft
  • $484/SF
  • 91 Days On Market

  • 2 Beds
  • 4 Baths
  • Built 2022

  19 Wallace Way Unit 25, Chappaqua, NY 10514

  FULLY DECORATED AND FURNISHED MODEL HOME FOR SALE. 3432’ ‘Square Feet, 2 BR Byram Farmhouse. This model home includes an array of Luxury upgrades, which you can enjoy and move into this school year (Fall 2025). The Byram includes a finished basement with half bath and many more luxurious finishes. The open concept great room and kitchen allow for large family gatherings. The open island with

  Andrea Martone Houlihan Lawrence Inc.

  19 Wallace Way Unit 25, Chappaqua, NY 10514
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  Est $1,022,710 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,740 Sq Ft

  625 Quaker Rd, Chappaqua, NY 10514

  625 Quaker Rd, Chappaqua, NY 10514
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  /7

  $1,658,995 Pending

  • 2 Beds
  • 3.5 Baths
  • 3,353 Sq Ft

  11 Wallace Way Unit 18, Chappaqua, NY 10514

  To be Built! Spring 2025 move-in. 3485 square feet ! Still time to personalize interior finishes at our luxury Design Studio. Final building for sale at Chappaqua Crossing! A roaring fireplace will warm the entire home. A private rooftop terrace with included outdoor gas fireplace, 2- car garage and the highest quality interior appointments you've come to expect from Toll Brothers round out this

  Andrea Martone Houlihan Lawrence Inc.

  11 Wallace Way Unit 18, Chappaqua, NY 10514
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  $3,400,000 Sold Sep 09, 2025

  • 7,305 Sq Ft
  • $465/SF
  • 65 Days On Market

  • 4 Beds
  • 7 Baths
  • Built 2007

  5 Briarcliff Rd, Chappaqua, NY 10514

  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

  5 Briarcliff Rd, Chappaqua, NY 10514
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  Est $1,186,548 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,830 Sq Ft

  1283 Hardscrabble Rd, Chappaqua, NY 10514

  1283 Hardscrabble Rd, Chappaqua, NY 10514
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  /5

  $1,599,995 Pending

  • 3 Beds
  • 3.5 Baths
  • 3,353 Sq Ft

  15 Wallace Way Unit 20, Chappaqua, NY 10514

  TO BE BUILT. Move-in Spring 2026. Spacious 3485 square feet ! Still time to personalize interior finishes by visiting our luxurious Design Studio. As you enter the Millwood Elite, 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

  Andrea Martone Houlihan Lawrence Inc.

  15 Wallace Way Unit 20, Chappaqua, NY 10514
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  $1,280,000 Sold Sep 03, 2025

  • 2,212 Sq Ft
  • $579/SF
  • 14 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1934

  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
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  Est $2,520,117 Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 6,349 Sq Ft

  650 Quaker Rd, Chappaqua, NY 10514

  650 Quaker Rd, Chappaqua, NY 10514
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  /4

  $1,399,995 Pending

  • 2 Beds
  • 3.5 Baths
  • 2,945 Sq Ft

  13 Wallace Way Unit 19 Briarcliff Tradit, Chappaqua, NY 10514

  2 BR Primary on first floor home. Large Eat in kitchen with island, open to great room and dining room. Second floor office and wet bar makes entertaining easy on rooftop terrace with built-in kitchen BBQ. Lower level is finished with media room and full bath.

  Thomas Jacovino Toll Brothers Real Estate Inc.

  13 Wallace Way Unit 19 Briarcliff Tradit, Chappaqua, NY 10514
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  $1,850,000 Sold Sep 02, 2025

  • 3,102 Sq Ft
  • $596/SF
  • 7 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1959

  42 Cross Ridge Rd, Chappaqua, NY 10514

  Meticulously maintained move-in ready home on a park-like acre with an incredible flat, usable and private backyard with extensive mature trees and landscaping. This 3 bedroom/ 3 full bathroom house with hardwood flooring and recessed lighting throughout, has a perfect option for an additional guest bedroom/ office on the first floor and countless special features such as an in-ground sprinkler

  Pamela Akin Douglas Elliman Real Estate

  42 Cross Ridge Rd, Chappaqua, NY 10514
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  Est $1,769,008 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,307 Sq Ft

  20 Suzanne Ln, Chappaqua, NY 10514

  20 Suzanne Ln, Chappaqua, NY 10514
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  /33

  $999,000 Coming Soon

  • 3 Beds
  • 2 Baths
  • 2,220 Sq Ft

  105 Douglas Rd, Chappaqua, NY 10514

  Welcome to this unique and charming carriage home nestled in the heart of Chappaqua. Bright and sunny, set on a private 1.4-acre lot. This well-maintained residence blends timeless character with modern updates.Step inside to a welcoming entry foyer that leads to a spacious living room, complete with a cozy fireplace and French doors opening to a secluded patio — perfect for entertaining or

  Al Posillico Keller Williams Realty Group

  105 Douglas Rd, Chappaqua, NY 10514

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