Chappaqua, NY Homes

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  $950,000

  Open Sat 1PM - 3PM Coming Soon

  • 3 Beds
  • 2 Baths
  • 2,380 Sq Ft

  42 Hollow Oak Rd, Chappaqua, NY 10514

  Welcome to 42 Hollow Oak Road, a captivating 3-bedroom, 2-bathroom sanctuary nestled in the heart of Chappaqua. Spanning 2,380 square feet, this home perfectly balances suburban tranquility with modern convenience. Step inside to discover a bright, airy layout flooded with natural light. The spacious living areas feature warm hardwood floors, fireplace and a seamless flow, ideal for daily living

  Bradley Brammer Julia B Fee Sothebys Int. Rlty

  42 Hollow Oak Rd, Chappaqua, NY 10514
• Explore Chappaqua

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  /25

  Starting at $3,237 Per Month

  • 2 Beds

  480 Bedford Rd, Chappaqua, NY 10514

  Wilder Balter Partners, Inc., Hudson valley's premier developer of luxury homes has written a new chapter for the iconic reader's digest building. The four-story structure has undergone an unprecedented renovation, and the finished product embraces the nostalgia of the old media empire's headquarters with the extravagance of contemporary housing. Chappaqua Crossing Apts is now open! Please call

  Chappaqua Crossing Apartments

  

  480 Bedford Rd, Chappaqua, NY 10514
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  $1,600,000

  Sold Feb 27, 2026

  36 Pond Hill Rd, Chappaqua, NY 10514

  • 3 Beds
  • 3.5 Baths
  • 2,866 Sq Ft
  • Built 1952

  Last Sold Summary

  • 23% Above List Price
  • $558/SF
  • 11 Days On Market

  Current Estimated Value $1,599,474

  Last Listing Agent Danae Richards William Raveis-New York, LLC

  36 Pond Hill Rd, Chappaqua, NY 10514
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  Est $1,400,667

  Not Listed For Sale

  27 Hardscrabble Hill Rd, Chappaqua, NY 10514

  • 3 Beds
  • 2.5 Baths
  • 1,995 Sq Ft
  • Built 1960

  27 Hardscrabble Hill Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Pamela Akin Douglas Elliman Real Estate
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  /29

  $1,199,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,207 Sq Ft

  21 Campfire Rd, Chappaqua, NY 10514

  Move right into this sparkling, beautifully updated 4-bedroom Colonial, ideally located in the highly sought-after Chappaqua School District. Blending timeless pre-war charm with modern amenities, this home offers exceptional comfort and style. Freshly painted inside and out, the home features beautiful hardwood floors, recessed lighting, a renovated kitchen, updated bathrooms, a wood burning

  Cindy Glynn Compass Greater NY, LLC

  21 Campfire Rd, Chappaqua, NY 10514
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  /17

  $4,500 Per Month

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • House for Rent

  547 King St Unit A, Chappaqua, NY 10514

  Charming Village Rental with outdoor space in Chappaqua! Step into the timeless charm of this 2-bedroom, 1 -bath rental nestled in a classic Chappaqua home, where character and comfort come together in one of the area's most convenient location. Just a short distance from the village, you'll enjoy easy access to local cafes, restaurants, boutique shops, parks, and the Metro-North train station,

  Patricia DelVecchio William Raveis Real Estate

  547 King St Unit A, Chappaqua, NY 10514
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  $1,345,014

  Sold Jul 29, 2026

  14 Aldridge Rd, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 2,478 Sq Ft
  • Built 1920

  Last Sold Summary

  • 8% Above List Price
  • $543/SF
  • 20 Days On Market

  Current Estimated Value $1,297,447

  Last Listing Agent Sena Baron William Raveis-New York, LLC

  14 Aldridge Rd, Chappaqua, NY 10514
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  Est $1,784,639

  Not Listed For Sale

  34 Hardscrabble Hill Rd, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,700 Sq Ft
  • Built 2014

  34 Hardscrabble Hill Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent Mary Ann Tighe Houlihan Lawrence Inc.
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  $2,649,000

  $50K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 5,918 Sq Ft

  40 Hamilton Dr, Chappaqua, NY 10514

  Tucked away on over two exquisitely landscaped acres in one of Chappaqua’s most prestigious enclaves, this exceptional newly constructed modern home redefines luxury living through a masterful blend of architectural sophistication, cutting-edge efficiency, and timeless elegance. Designed with a discerning eye and crafted with uncompromising quality, this magazine-worthy residence offers the

  Matthew Valvano Berkshire Hathaway HS NY Prop

  40 Hamilton Dr, Chappaqua, NY 10514
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  /45

  $10,999 Per Month

  • 3 Beds
  • 3.5 Baths
  • 3,202 Sq Ft
  • Modern Farmhouse 3 Bedroom 3.5 Bathroom

  1111 Hardscrabble Rd, Chappaqua, NY 10514

  Experience refined country living in this beautifully crafted custom modern farmhouse, ideally located just minutes from downtown Chappaqua, local shops, restaurants, and the Metro-North train station. Set on a level, private property, this thoughtfully designed home blends timeless charm with modern comfort.The main level features a spacious primary bedroom suite, offering the

  1111 Hardscrabble Rd, Chappaqua, NY 10514
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  $2,825,000

  Sold Dec 15, 2025

  70 Haights Cross Rd, Chappaqua, NY 10514

  • 5 Beds
  • 9 Baths
  • 8,775 Sq Ft
  • Built 2005

  Last Sold Summary

  • 10% Below List Price
  • $322/SF
  • 159 Days On Market

  Current Estimated Value $3,178,173

  Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.

  70 Haights Cross Rd, Chappaqua, NY 10514
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  Est $1,492,000

  Not Listed For Sale

  265 Mill River Rd, Chappaqua, NY 10514

  • 4 Beds
  • 4.5 Baths
  • 4,811 Sq Ft
  • Built 2010

  265 Mill River Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 68 Days On Market

  Last Listing Agent Sandra Cappucci Julia B Fee Sothebys Int. Rlty
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  /39

  $1,199,000

  Pending

  • 3 Beds
  • 3.5 Baths
  • 2,708 Sq Ft

  25 Cabin Ridge Rd, Chappaqua, NY 10514

  Escape to your own private retreat on 3.44 acres of wooded land, where rustic charm meets modern comfort. This unique residence was thoughtfully expanded in 2005 and refined with modern luxuries while preserving its timeless character. The beautifully crafted, freshly painted 2,708-square-foot home offers 3 bedrooms and 4 bathrooms in a serene, nature-filled setting. Inside, you'll find a

  Jia Wei Keller Williams Realty Group

  25 Cabin Ridge Rd, Chappaqua, NY 10514
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  $4,750 Per Month

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Apartment for Rent

  82 Douglas Rd Unit B, Chappaqua, NY 10514

  Beautifully renovated second-floor 2-bedroom, 1-bath apartment just a short walk to the Chappaqua train station, downtown shops and restaurants. This light-filled home offers approximately 1,200 square feet of thoughtfully updated living space featuring hardwood floors throughout, a stunning designer kitchen with quartz countertops, stainless steel appliances, shaker cabinetry, subway tile

  Michael Parelli Mike Parelli Real Estate LLC

  82 Douglas Rd Unit B, Chappaqua, NY 10514
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  $805,000

  Sold Nov 21, 2025

  149 King St Unit 4, Chappaqua, NY 10514

  • 2 Beds
  • 2.5 Baths
  • 1,767 Sq Ft
  • Built 1988

  Last Sold Summary

  • 6% Below List Price
  • $456/SF
  • 105 Days On Market

  Last Listing Agent Nancy Jones Julia B Fee Sothebys Int. Rlty

  149 King St Unit 4, Chappaqua, NY 10514
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  Est $844,980

  Not Listed For Sale

  70 Leroy Rd, Chappaqua, NY 10514

  70 Leroy Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 56 Days On Market

  Last Listing Agent Jaimme Pudalov Houlihan Lawrence Inc.
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  /21

  $1,195,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,178 Sq Ft

  26 Meadow Ln, Chappaqua, NY 10514

  Welcome to 26 Meadow Lane, a pristine 2,178-square-foot ranch set on over half an acre of flat, beautifully landscaped property in one of Chappaqua’s most coveted residential neighborhoods. A rocking chair front porch and Belgian block-lined driveway offer an immediate sense of arrival, while sidewalk-lined streets connect the neighborhood to the acclaimed village of Chappaqua, minutes from

  Lauren Zaccaria Houlihan Lawrence Inc.

  26 Meadow Ln, Chappaqua, NY 10514
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  /25

  $6,600 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,129 Sq Ft
  • Townhouse for Rent

  9 Deer Run, Chappaqua, NY 10514

  Move right into this spacious Chappaqua end-unit condominium, ready for immediate occupancy. Located just a short distance from town, shops, restaurants and Metro-North, this sought-after community offers exceptional amenities, including a swimming pool, fitness center, tennis courts and clubhouse. One of the largest homes in the complex, this light-filled residence features three bedrooms and

  Sari Shaw Compass Greater NY, LLC

  9 Deer Run, Chappaqua, NY 10514
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  $1,905,000

  Sold Jun 02, 2026

  110 Marcourt Dr, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 2,921 Sq Ft
  • Built 1961

  Last Sold Summary

  • 34% Above List Price
  • $652/SF
  • 6 Days On Market

  Current Estimated Value $1,797,665

  Last Listing Agent Stephanie Garbuio Houlihan Lawrence Inc.

  110 Marcourt Dr, Chappaqua, NY 10514
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  Not Listed For Sale

  6 Dewitt Dr Unit 65, Chappaqua, NY 10514

  • 2 Beds
  • 3.5 Baths
  • 3,353 Sq Ft
  • Built 2025

  6 Dewitt Dr Unit 65, Chappaqua, NY 10514

  Last Sold Summary

  • 66 Days On Market

  Last Listing Agent Andrea Martone Houlihan Lawrence Inc.
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  /39

  $1,599,999

  Pending

  • 4 Beds
  • 3 Baths
  • 3,672 Sq Ft

  734 King St, Chappaqua, NY 10514

  Thoughtfully reimagined farmhouse with barn, this distinctive 4-bedroom, 3-bath home blends historic charm with striking modern design. Set on close to 2 private acres surrounded by mature trees, the property offers exceptional privacy and a peaceful natural setting. Inside, soaring ceilings, oversized windows, and multiple skylights flood the home with natural light. The open-concept living

  Sari Shaw Compass Greater NY, LLC

  734 King St, Chappaqua, NY 10514
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  /16

  $4,300 Per Month

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Apartment for Rent

  91 Bedford Rd Unit 2, Chappaqua, NY 10514

  Unparalleled opportunity to attain one of the only 2 exceptional apartments in the corner turret at the newly constructed building in the heart of Chappaqua. Quality construction by a highly regarded local builder. This apartment features a stunning octagonal living room/dining room, 2 bedrooms and 2 full baths/ADA shower. Glamorous modern styling quartz counters, island open to bright open floor

  Grace Priore ERA Insite Realty Services

  91 Bedford Rd Unit 2, Chappaqua, NY 10514
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  $1,465,000

  Sold Oct 01, 2025

  33 High Way, Chappaqua, NY 10514

  • 3 Beds
  • 3.5 Baths
  • 1,917 Sq Ft
  • Built 1938

  Last Sold Summary

  • 22% Above List Price
  • $764/SF
  • 11 Days On Market

  Current Estimated Value $1,537,091

  Last Listing Agent Jennifer Harris Compass Greater NY, LLC

  33 High Way, Chappaqua, NY 10514
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  Not Listed For Sale

  22 Dewitt Dr Unit 73, Chappaqua, NY 10514

  • 3 Beds
  • 3.5 Baths
  • 3,352 Sq Ft
  • Built 2025

  22 Dewitt Dr Unit 73, Chappaqua, NY 10514

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Thomas Jacovino Toll Brothers Real Estate Inc.
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  /49

  $1,100,000

  Pending

  • 5 Beds
  • 3 Baths
  • 2,715 Sq Ft

  2 Turner Dr, Chappaqua, NY 10514

  Some homes have good bones. This one has great ones in a private setting. Nestled in Chappaqua's beloved Seven Bridges neighborhood, this 1934 Colonial sits on nearly three-quarters of an acre where tree-lined streets and a true sense of community appeal to buyers who embrace Chappaqua and remain for years. Original hardwood floors, a wood-burning fireplace, crown molding, and a screened porch

  Lauren Zaccaria Houlihan Lawrence Inc.

  2 Turner Dr, Chappaqua, NY 10514
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  /28

  $6,000 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,130 Sq Ft
  • House for Rent

  480 King St, Chappaqua, NY 10514

  Welcome to this pristine 2-bedroom Cape Cod-style home , offering a versatile layout that effortlessly lives like a 3-bedroom. Exuding charm and meticulous care throughout, the residence features 2 full bathrooms and a convenient half-bath. Its center-of-town location puts local shops, dining, and community conveniences right at your doorstep, making it a perfect blend of style, comfort, and

  Nancy Musich Houlihan Lawrence Inc.

  480 King St, Chappaqua, NY 10514
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  $1,550,000

  Sold Jan 20, 2026

  100 Old Farm Rd N, Chappaqua, NY 10514

  • 3 Beds
  • 2.5 Baths
  • 2,971 Sq Ft
  • Built 2010

  Last Sold Summary

  • 19% Above List Price
  • $522/SF
  • 13 Days On Market

  Current Estimated Value $1,552,024

  Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.

  100 Old Farm Rd N, Chappaqua, NY 10514
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  Not Listed For Sale

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

  • 1 Bed
  • 1 Bath
  • 814 Sq Ft
  • Built 1984

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

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Alicja Bohmrich Houlihan Lawrence Inc.
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  $1,594,000

  $101K PRICE DROP

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

  676 Hardscrabble Rd, Chappaqua, NY 10514

  Renovated and Reimagined Colonial on Spectacular Park-Like Grounds, this exceptional residence includes a separate cottage-style bonus building that offers endless possibilities. Whether envisioned as a private home office, artist’s studio, yoga or fitness center, man cave or an inspiring creative workspace, this detached structure provides exceptional flexibility and privacy. Nestled amid the

  Elvira Aloia Corcoran Legends Realty

  676 Hardscrabble Rd, Chappaqua, NY 10514
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  /16

  $6,000 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,569 Sq Ft
  • Townhouse for Rent

  56 Rambling Brook Rd, Chappaqua, NY 10514

  Spacious and sun drenched 3 bedroom, 2.5 bath townhouse with an attached 1 car garage, private driveway, and abundant storage in the highly desirable Old Farm Lake community, located within the award winning Chappaqua School District. This bright, updated, and well maintained home offers comfortable living space, thoughtfully designed for both everyday living and entertaining. Enjoy a private

  Wendy Nolan Houlihan Lawrence Inc.

  56 Rambling Brook Rd, Chappaqua, NY 10514
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  $1,659,995

  Sold Sep 10, 2025

  19 Wallace Way Unit 25, Chappaqua, NY 10514

  • 2 Beds
  • 4 Baths
  • 3,432 Sq Ft
  • Built 2022

  Last Sold Summary

  • 4% Below List Price
  • $484/SF
  • 91 Days On Market

  Current Estimated Value $1,807,390

  Last Listing Agent Andrea Martone Houlihan Lawrence Inc.

  19 Wallace Way Unit 25, Chappaqua, NY 10514
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  Not Listed For Sale

  149 King St Unit 19, Chappaqua, NY 10514

  • 2 Beds
  • 2.5 Baths
  • 1,664 Sq Ft
  • Built 1988

  149 King St Unit 19, Chappaqua, NY 10514

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Alicja Bohmrich Houlihan Lawrence Inc.
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  /23

  $1,590,000

  $35K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 2,576 Sq Ft

  17 Lila Ln, Chappaqua, NY 10514

  Welcome to this sophisticated carriage home at 17 Lila Lane, offering a rare blend of contemporary luxury and maintenance-free living within the prestigious Chappaqua Crossing community. The thoughtfully designed layout is anchored by a gorgeous chef’s kitchen, featuring a large center island with ample seating and a premium JennAir appliance package. Equally enticing is the coveted first-floor

  Jocelyn Cloder Compass Greater NY, LLC

  17 Lila Ln, Chappaqua, NY 10514
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  /32

  $5,900 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,553 Sq Ft
  • Townhouse for Rent

  17 Rambling Brook Rd, Chappaqua, NY 10514

  Move In Ready, Recently Remodeled Townhouse in Old Farm Lake, Chappaqua. Discover this beautifully updated end unit townhouse offering 3 bedrooms, 3 baths, one car garage, deck, and a bonus room on each level. With a natural organic feel to compliment quiet community settings and landscaping, your new home offers calming sensory attentive features throughout to fit any mood. Enjoy New Designer

  Lauren Zaccaria Houlihan Lawrence Inc.

  17 Rambling Brook Rd, Chappaqua, NY 10514
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  $3,400,000

  Sold Sep 09, 2025

  5 Briarcliff Rd, Chappaqua, NY 10514

  • 4 Beds
  • 7 Baths
  • 7,305 Sq Ft
  • Built 2007

  Last Sold Summary

  • 8% Below List Price
  • $465/SF
  • 65 Days On Market

  Current Estimated Value $3,693,183

  Last Listing Agent Sari Shaw Compass Greater NY, LLC

  5 Briarcliff Rd, Chappaqua, NY 10514
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  Not Listed For Sale

  9 Dewitt Dr Unit 80, Chappaqua, NY 10514

  • 2 Beds
  • 3.5 Baths
  • 3,269 Sq Ft
  • Built 2025

  9 Dewitt Dr Unit 80, Chappaqua, NY 10514

  Last Sold Summary

  • 46 Days On Market

  Last Listing Agent Thomas Jacovino Toll Brothers Real Estate Inc.
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  /27

  $579,000

  Pending

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft

  309 N Greeley Ave Unit 5C, Chappaqua, NY 10514

  Welcome to 309 N. Greeley Avenue. This lovely first floor Town House in the sought-after Chestnut Oaks Community is conveniently located to the heart of downtown Chappaqua. With the award-winning Chappaqua School District and proximity to a Metro North station, this property will not last! This Two Bed, 1 Bath unit has a great layout with a front and back patio! There are no stairs (just one

  Daniel Berger RE/MAX Prestige Properties

  309 N Greeley Ave Unit 5C, Chappaqua, NY 10514
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  $820,000

  Sold Aug 20, 2025

  149 King St Unit 15, Chappaqua, NY 10514

  • 2 Beds
  • 2.5 Baths
  • 1,925 Sq Ft
  • Built 1988

  Last Sold Summary

  • $426/SF
  • 15 Days On Market

  Last Listing Agent Janet Short Houlihan Lawrence Inc.

  149 King St Unit 15, Chappaqua, NY 10514
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  Not Listed For Sale

  150 N Bedford Rd Unit C9, Chappaqua, NY 10514

  • 1 Bed
  • 1 Bath
  • 980 Sq Ft
  • Built 1983

  150 N Bedford Rd Unit C9, Chappaqua, NY 10514

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Jessica Broomhead Compass Greater NY, LLC
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  /39

  $2,195,000

  Pending

  • 6 Beds
  • 5.5 Baths
  • 6,563 Sq Ft

  22 Random Farms Cir, Chappaqua, NY 10514

  Set on a picturesque property in sought-after Random Farms, this stunning 6-bedroom residence offers dramatic views, soaring ceilings, and exceptional living spaces designed for both everyday comfort and elegant entertaining. A breathtaking double-height entry welcomes you into sun-drenched interiors featuring walls of windows, rich hardwood floors, and seamless open-concept flow

  Sari Shaw Compass Greater NY, LLC

  22 Random Farms Cir, Chappaqua, NY 10514

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