Chappaqua, NY Homes

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  /36

  $2,499,000

  $101K PRICE DROP Pending

  • 5 Beds
  • 4.5 Baths
  • 4,482 Sq Ft

  34 Pebblebrook Way, Chappaqua, NY 10514

  The only triple mint move-in condition house in Chappaqua schools. Nestled within 1.65 acres in the sought-after Hardscrabble Lake development and Chappaqua school district, this rare find modern Center Hall Colonial home epitomizes luxury living. If you are searching for a masterpiece beautifully finished home that is turnkey inside and out, this is your home. This meticulously thought-out home

  Natalia Wixom Compass Greater NY, LLC

  34 Pebblebrook Way, Chappaqua, NY 10514
• 

  $1,290,000

  Sold Jan 21, 2026

  71 Commodore Rd, Chappaqua, NY 10514

  • 3 Beds
  • 2 Baths
  • 1,957 Sq Ft
  • Built 1955

  Last Sold Summary

  • 11% Below List Price
  • $659/SF
  • 37 Days On Market

  Current Estimated Value $1,314,792

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  71 Commodore Rd, Chappaqua, NY 10514
• 

  Est $1,953,892

  Not Listed For Sale

  55 Cowdin Cir, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 4,045 Sq Ft
  • Built 1952

  55 Cowdin Cir, Chappaqua, NY 10514

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Eric Stein RE/MAX Distinguished Hms.&Prop
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  /35

  $549,000

  $301K PRICE DROP Pending

  • 2 Beds
  • 1 Bath
  • 711 Sq Ft

  58 Maple Ave, Chappaqua, NY 10514

  Opportunities like this do not come around often in Chappaqua, and when they do, they tend to move quickly. What is being offered at 58 Maple Ave is a flat, level, in-town parcel with an existing 2-bedroom, 1-bath cottage set back from the road among towering pines, in one of Westchester County's most coveted villages. Whether a buyer chooses to develop the land, renovate what is there, or simply

  Christian Lugo Howard Hanna Rand Realty

  58 Maple Ave, Chappaqua, NY 10514
• 

  $2,025,000

  Sold Jul 22, 2026

  40 Kings Ct, Chappaqua, NY 10514

  • 3 Beds
  • 2.5 Baths
  • 3,121 Sq Ft
  • Built 1939

  Last Sold Summary

  • 27% Above List Price
  • $649/SF
  • 13 Days On Market

  Current Estimated Value $1,587,092

  Last Listing Agent Jennifer Harris Compass Greater NY, LLC

  40 Kings Ct, Chappaqua, NY 10514
• 

  Est $2,008,269

  Not Listed For Sale

  70 Cowdin Cir, Chappaqua, NY 10514

  • 4 Beds
  • 4 Baths
  • 3,689 Sq Ft
  • Built 1963

  70 Cowdin Cir, Chappaqua, NY 10514

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.
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  /44

  $1,399,000

  Pending

  • 3 Beds
  • 3 Baths
  • 2,821 Sq Ft

  10 Deborah Ln, Chappaqua, NY 10514

  SoHo in Chappaqua! Chappaqua schools! Dramatic, Airy and Light-filled 3 Bedroom Contemporary in immaculate condition located in sought-after neighborhood and Cul-De-Sac. Set on almost an acre of private property with rocking-chair front porch. Elegant living room features a soaring cathedral ceiling, wall of built-in bookshelves and wall of windows opening to dining area with access to deck.

  Alicja Bohmrich Houlihan Lawrence Inc.

  10 Deborah Ln, Chappaqua, NY 10514
• 

  $2,000,000

  Sold Feb 09, 2026

  2 Whippoorwill Close, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,022 Sq Ft
  • Built 1980

  Last Sold Summary

  • 14% Above List Price
  • $662/SF
  • 4 Days On Market

  Current Estimated Value $1,956,749

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  2 Whippoorwill Close, Chappaqua, NY 10514
• 

  Est $1,751,550

  Not Listed For Sale

  64 Cowdin Cir, Chappaqua, NY 10514

  • 3 Beds
  • 2.5 Baths
  • 2,911 Sq Ft
  • Built 1962

  64 Cowdin Cir, Chappaqua, NY 10514

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.
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  /43

  $2,299,000

  Open Sat 1PM - 3PM Coming Soon

  • 5 Beds
  • 4.5 Baths
  • 4,661 Sq Ft

  20 Hitching Post Ln, Chappaqua, NY 10514

  Welcome to 20 Hitching Post Lane in Chappaqua, New York. This five-bedroom, 4.1 bath Colonial is set on over 2 bucolic acres on a beautiful tree-lined street. An impressive oak floored entry foyer with cherry inlay opens to a spacious formal living room with crown moldings and new windows (2023), warmed by a wood burning fireplace with decorative mantle. The adjacent family room has a second wood

  John Buckley William Raveis-New York LLC

  20 Hitching Post Ln, Chappaqua, NY 10514
• 

  $1,455,000

  Sold Jul 22, 2026

  28 Valley View Rd, Chappaqua, NY 10514

  • 3 Beds
  • 2 Baths
  • 1,999 Sq Ft
  • Built 1956

  Last Sold Summary

  • 32% Above List Price
  • $728/SF
  • 9 Days On Market

  Current Estimated Value $1,119,928

  Last Listing Agent Kile Boga-Ibric Houlihan Lawrence Inc.

  28 Valley View Rd, Chappaqua, NY 10514
• 

  Est $2,733,935

  Not Listed For Sale

  76 Cowdin Ln, Chappaqua, NY 10514

  • 4 Beds
  • 6 Baths
  • 5,600 Sq Ft
  • Built 1962

  76 Cowdin Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Yona Strougo Compass Greater NY, LLC
• 

  

  /17

  $649,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,458 Sq Ft

  353 N Greeley Ave Unit 353, Chappaqua, NY 10514

  Welcome to Chestnut Oaks. Corner unit Townhome located in building 5 featuring 2 bedrooms, 2 full baths, fireplace, attached garage and balcony. Located in the heart of Chappaqua and close to train, town and schools. Renovated in 2010 with new dine-in kitchen, granite counter tops, stainless steel appliances, hardwood floors, renovated primary bathroom, custom walk-in closet, new washer/dryer and

  Toni DiMichelo Houlihan Lawrence Inc.

  353 N Greeley Ave Unit 353, Chappaqua, NY 10514
• 

  $1,720,000

  Sold Feb 04, 2026

  6 Whippoorwill Lake Rd, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,244 Sq Ft
  • Built 1979

  Last Sold Summary

  • 4% Above List Price
  • $530/SF
  • 25 Days On Market

  Current Estimated Value $1,785,288

  Last Listing Agent Sari Shaw Compass Greater NY, LLC

  6 Whippoorwill Lake Rd, Chappaqua, NY 10514
• 

  Est $3,360,018

  Not Listed For Sale

  63 Cowdin Ln, Chappaqua, NY 10514

  • 4 Beds
  • 5.5 Baths
  • 7,764 Sq Ft
  • Built 2007

  63 Cowdin Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC
• 

  

  /31

  $1,725,000

  • 4 Beds
  • 3.5 Baths
  • 3,581 Sq Ft

  53 W Orchard Rd, Chappaqua, NY 10514

  Welcome to an exceptional move-in ready home located in a highly desirable Chappaqua neighborhood known for its award-winning schools & sought-after lifestyle. Perfectly positioned in a quiet neighborhood, this stunning property offers privacy, space & luxury living at its finest. In addition, easy access to the North County Trail for any outdoor activities of your choice. Step inside & you'll

  Lori Meringolo Houlihan Lawrence Inc.

  53 W Orchard Rd, Chappaqua, NY 10514
• 

  $2,000,000

  Sold Apr 28, 2026

  40 Smith St, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 2,658 Sq Ft
  • Built 1927

  Last Sold Summary

  • 38% Above List Price
  • $752/SF
  • 7 Days On Market

  Current Estimated Value $1,830,770

  Last Listing Agent Joanna Rizoulis Julia B Fee Sothebys Int. Rlty

  40 Smith St, Chappaqua, NY 10514
• 

  Est $2,339,947

  Not Listed For Sale

  70 Cowdin Ln, Chappaqua, NY 10514

  • 4 Beds
  • 4 Baths
  • 5,309 Sq Ft
  • Built 1987

  70 Cowdin Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 97 Days On Market

  Last Listing Agent Suzanne Sanborn William Raveis Real Estate
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  /27

  $1,590,000

  • 3 Beds
  • 3.5 Baths
  • 2,690 Sq Ft

  131 Douglas Rd, Chappaqua, NY 10514

  Tastefully Expanded and Renovated Colonial in the Heart of Chappaqua - New 4 bedroom Septic, 2024 Roof and Exceptional Indoor/Outdoor Living. Just moments to Chappaqua village, Metro North and highly regarded Chappaqua schools. A flexible first-floor guest/au pair suite with private bath, chefs kitchen with Wolf appliances, private primary suite, 2 fireplaces, expansive deck and mature grounds

  Toni DiMichelo Houlihan Lawrence Inc.

  131 Douglas Rd, Chappaqua, NY 10514
• 

  $1,320,000

  Sold Dec 11, 2025

  41 Valley Ln, Chappaqua, NY 10514

  • 3 Beds
  • 2.5 Baths
  • 2,034 Sq Ft
  • Built 1972

  Last Sold Summary

  • 2% Above List Price
  • $649/SF
  • 10 Days On Market

  Current Estimated Value $1,365,768

  Last Listing Agent Amanda Goldberg William Raveis-New York, LLC

  41 Valley Ln, Chappaqua, NY 10514
• 

  Est $1,715,117

  Not Listed For Sale

  9 Killington St, Chappaqua, NY 10514

  • 3 Beds
  • 3 Baths
  • 2,625 Sq Ft
  • Built 1968

  9 Killington St, Chappaqua, NY 10514

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Natalia Wixom Compass Greater NY, LLC
• 

  

  /49

  $1,800,000

  Open Sat 12PM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 2,913 Sq Ft

  406 Bedford Rd, Chappaqua, NY 10514

  Welcome to this beautifully maintained almost 3000 sq ft 4 bedroom 4 bath Colonial set on a private, sun-filled one acre property framed by mature trees, a classic stone wall , and meticulously maintained landscaping and plantings.Elegance and craftsmanship are evident throughout with beautiful hardwood floors, generously sized bedrooms and a primary suite with private en-suite bath. At

  Donna Powers-Amori Howard Hanna Rand Realty

  406 Bedford Rd, Chappaqua, NY 10514
• 

  $1,376,000

  Sold Jul 23, 2026

  65 Douglas Rd, Chappaqua, NY 10514

  • 3 Beds
  • 2 Baths
  • 1,702 Sq Ft
  • Built 1930

  Last Sold Summary

  • 10% Above List Price
  • $808/SF
  • 17 Days On Market

  Current Estimated Value $1,243,114

  Last Listing Agent Lynn Harmonay North Country Sothebys Int Rlt

  65 Douglas Rd, Chappaqua, NY 10514
• 

  Est $1,770,061

  Not Listed For Sale

  395 Bedford Rd, Chappaqua, NY 10514

  • 5 Beds
  • 3.5 Baths
  • 3,041 Sq Ft
  • Built 1955

  395 Bedford Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Catherine O'Connor Houlihan Lawrence Inc.
• 

  

  /30

  $809,000

  $20K PRICE DROP Pending

  • 4 Beds
  • 2.5 Baths
  • 1,584 Sq Ft

  73 S Bedford Rd, Chappaqua, NY 10514

  Welcome home to this well-maintained residence in the heart of vibrant Chappaqua! This 4 bedroom and 2.5 full bathroom house is located in the award-winning Chappaqua school district. Step inside to discover gleaming hardwood floors throughout, a cozy living room with a wood-burning fireplace, and a bright, charming dining room. The kitchen features ample cabinetry, granite countertops, and

  Thomas Hennerty Thomas S. Hennerty

  73 S Bedford Rd, Chappaqua, NY 10514
• 

  $1,745,000

  Sold Aug 03, 2026

  2 Dewitt Dr, Chappaqua, NY 10514

  • 2 Beds
  • 3.5 Baths
  • 3,574 Sq Ft
  • Built 2025

  Last Sold Summary

  • 8% Below List Price
  • $488/SF
  • 73 Days On Market

  Last Listing Agent Joann Galluccio William Raveis-New York LLC

  2 Dewitt Dr, Chappaqua, NY 10514
• 

  Est $2,707,571

  Not Listed For Sale

  35 Ivy Hill Rd, Chappaqua, NY 10514

  • 5 Beds
  • 4.5 Baths
  • 4,004 Sq Ft
  • Built 1942

  35 Ivy Hill Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 47 Days On Market

  Last Listing Agent Stacy Levey William Raveis-New York, LLC
• 

  

  /30

  $749,000

  • 3 Beds
  • 1.5 Baths
  • 1,414 Sq Ft

  27 Mill River Rd, Chappaqua, NY 10514

  You’ll be hard-pressed to find a turn-key home like this—especially at this price—in the Chappaqua School District, let alone Westchester County! Welcome to this charming 1850s Colonial, ideally situated in the heart of Chappaqua, just 0.3 miles on foot via a convenient sidewalk to Metro-North and close to all that the village has to offer. With an easy walk to the train and convenient access by

  Johanna Kline Houlihan Lawrence Inc.

  27 Mill River Rd, Chappaqua, NY 10514
• 

  $1,725,000

  Sold Oct 31, 2025

  9 Point Place, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 4,100 Sq Ft
  • Built 2019

  Last Sold Summary

  • 11% Above List Price
  • $421/SF
  • 24 Days On Market

  Current Estimated Value $1,849,020

  Last Listing Agent Mark Boyland Keller Williams Realty Partner

  9 Point Place, Chappaqua, NY 10514
• 

  Est $2,802,316

  Not Listed For Sale

  17 Colony Row, Chappaqua, NY 10514

  • 4 Beds
  • 6 Baths
  • 5,680 Sq Ft
  • Built 1965

  17 Colony Row, Chappaqua, NY 10514

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC
• 

  

  /31

  $849,999

  $49K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,100 Sq Ft

  249 Mill River Rd, Chappaqua, NY 10514

  NOW Easy to Show Welcome to this beautifully maintained raised ranch offering the perfect blend of space, comfort, and convenience in a highly desirable Chappaqua P.O. location within the award-winning Pleasantville School District. Situated on a quiet cul-de-sac, this 4-bedroom, 2-bath home features soaring cathedral ceilings, rich red oak hardwood floors, and an inviting open layout designed

  Harry Donofrio Town and Village Real Estate

  249 Mill River Rd, Chappaqua, NY 10514
• 

  $2,250,000

  Sold Aug 11, 2026

  22 Random Farms Cir, Chappaqua, NY 10514

  • 6 Beds
  • 5.5 Baths
  • 6,563 Sq Ft
  • Built 1993

  Last Sold Summary

  • 3% Above List Price
  • $343/SF
  • 10 Days On Market

  Current Estimated Value $2,206,714

  Last Listing Agent Sari Shaw Compass Greater NY, LLC

  22 Random Farms Cir, Chappaqua, NY 10514
• 

  Est $3,138,186

  Not Listed For Sale

  26 Hemlock Hills, Chappaqua, NY 10514

  • 5 Beds
  • 6.5 Baths
  • 7,038 Sq Ft
  • Built 1989

  26 Hemlock Hills, Chappaqua, NY 10514

  Last Sold Summary

  • 63 Days On Market

  Last Listing Agent Wendy Alper Julia B Fee Sothebys Int. Rlty
• 

  

  /43

  $1,575,000

  $75K PRICE DROP Pending

  • 4 Beds
  • 4 Baths
  • 2,715 Sq Ft

  50 Ludlow Dr, Chappaqua, NY 10514

  Set on a sought-after cul-de-sac lined with charming classic homes, this 1938 Colonial masterfully blends period charm with today’s lifestyle needs. Set on a lovely private acre with flat lawns surrounded by towering trees yet nestled in a neighborhood setting, this 2,715 square foot center hall Colonial home offers 4 bedrooms, 2 full and 2 half baths. The heart of the home is the family room

  Sena Baron William Raveis-New York, LLC

  50 Ludlow Dr, Chappaqua, NY 10514
• 

  $1,391,022

  Sold Oct 23, 2025

  6 Algonquin Dr, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,776 Sq Ft
  • Built 1952

  Last Sold Summary

  • 16% Above List Price
  • $368/SF
  • 30 Days On Market

  Current Estimated Value $1,513,457

  Last Listing Agent Lindsay Rothman Compass Greater NY LLC

  6 Algonquin Dr, Chappaqua, NY 10514
• 

  Est $2,767,687

  Not Listed For Sale

  31 Hemlock Hills, Chappaqua, NY 10514

  • 4 Beds
  • 4.5 Baths
  • 6,187 Sq Ft
  • Built 1989

  31 Hemlock Hills, Chappaqua, NY 10514

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Judith Kelly Houlihan Lawrence Inc.
• 

  

  /31

  $1,375,000

  Coming Soon

  • 3 Beds
  • 2 Baths
  • 2,254 Sq Ft

  88 Brevoort Rd, Chappaqua, NY 10514

  Location, Location, Location and the yard you have dreamt of! Set on a gorgeous, level, private acre on a flat cul-de-sac street that leads to sidewalks to downtown Chappaqua, Grafflin Elementary, and Bell Middle School, and just minutes from Whole Foods, Lifetime Fitness, Greeley High School, and more. This well maintained 3-bedroom, 2-bath home, with only $21,452 in taxes, shows pride of

  Lori Hoffman-Chlapowski Compass Greater NY, LLC

  88 Brevoort Rd, Chappaqua, NY 10514
• 

  $732,500

  Sold Dec 15, 2025

  30 Rambling Brook Rd, Chappaqua, NY 10514

  • 2 Beds
  • 2.5 Baths
  • 1,244 Sq Ft
  • Built 1986

  Last Sold Summary

  • 2% Below List Price
  • $589/SF
  • 24 Days On Market

  Current Estimated Value $752,223

  Last Listing Agent Amanda Acard Nestedge Realty

  30 Rambling Brook Rd, Chappaqua, NY 10514
• 

  Est $2,030,637

  Not Listed For Sale

  50 Kerry Ln, Chappaqua, NY 10514

  • 4 Beds
  • 5 Baths
  • 4,051 Sq Ft
  • Built 1960

  50 Kerry Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Amy Singer Houlihan Lawrence Inc.
• 

  $1,731,000

  Sold Aug 06, 2026

  14 Crossways, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,138 Sq Ft
  • Built 1960

  Last Sold Summary

  • 8% Above List Price
  • $552/SF
  • 41 Days On Market

  Current Estimated Value $1,603,706

  Last Listing Agent Jonathan Cape Julia B Fee Sothebys Int. Rlty

  14 Crossways, Chappaqua, NY 10514

Showing Results 81 - 120, Page 3 of 18