Chappaqua, NY Homes

• 

  

  

  /33

  $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
• 

  $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 $1,305,059

  Not Listed For Sale

  6 Paula Place, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 5,272 Sq Ft
  • Built 2005

  6 Paula Place, Chappaqua, NY 10514

  Last Sold Summary

  • 85 Days On Market

  Last Listing Agent Joe Hasselt Joe Hasselt Real Estate
• 

  

  

  /36

  $1,550,000

  • 3 Beds
  • 2.5 Baths
  • 2,451 Sq Ft

  312 Quaker Rd, Chappaqua, NY 10514

  1926 Colonial with timeless character on a private and level half-acre, walkable to the train station and village in Chappaqua, NY. Circular driveway and classic curb appeal set the tone; inside, hardwood floors flow through an open, light-filled layout. The kitchen opens to a fireplaced family room with deck access, plus a formal dining room and a living room with its own wood-burning fireplace

  Edward Holmes William Raveis-New York, LLC

  312 Quaker 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 $941,724

  Not Listed For Sale

  15 Paula Place, Chappaqua, NY 10514

  • 2 Beds
  • 1 Bath
  • 1,160 Sq Ft
  • Built 1952

  15 Paula Place, Chappaqua, NY 10514

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Lauren Zaccaria Houlihan Lawrence Inc.
• 

  

  /24

  $685,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,299 Sq Ft

  80 Bischoff Ave, Chappaqua, NY 10514

  Experience the best of convenient living in this stylishly updated 3-bedroom home, perfectly situated in a walk-to-all neighborhood near the train, schools, shopping, and library. This meticulously maintained property boasts significant modern upgrades, including double pane windows, Hardiplank siding, and a spacious Trex deck overlooking a private, flat, grassy backyard. Inside, enjoy hardwood

  Jeremy Zucker Keller Williams NY Realty

  80 Bischoff Ave, Chappaqua, NY 10514
• 

  $1,747,995

  Sold Sep 19, 2025

  2 Carriage Ln Unit 81, Chappaqua, NY 10514

  • 2 Beds
  • 3.5 Baths
  • 3,269 Sq Ft
  • Built 2024

  Last Sold Summary

  • $535/SF
  • 235 Days On Market

  Current Estimated Value $1,950,615

  Last Listing Agent Thomas Jacovino Toll Brothers Real Estate Inc.

  2 Carriage Ln Unit 81, Chappaqua, NY 10514
• 

  Est $2,346,470

  Not Listed For Sale

  345 Roaring Brook Rd, Chappaqua, NY 10514

  • 4 Beds
  • 4.5 Baths
  • 5,668 Sq Ft
  • Built 1965

  345 Roaring Brook Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 24 Days On Market

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

  

  /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 $2,553,041

  Not Listed For Sale

  15 Kerry Ln, Chappaqua, NY 10514

  • 4 Beds
  • 4 Baths
  • 5,534 Sq Ft
  • Built 1935

  15 Kerry Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 128 Days On Market

  Last Listing Agent Janine Marino Houlihan Lawrence Inc.
• 

  

  /49

  $1,200,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,010 Sq Ft

  100 Devoe Rd, Chappaqua, NY 10514

  Location, location, location! Traditional 3-bedroom, 2.1-bath colonial-style home serenely set on a prime, flat 1.14-acre parcel. Covered front portico. Spacious living room with wood burning fireplace and hardwood flooring. Formal dining room with bay window, hardwood flooring and door to sunroom (additional 150sqft not included in total) with garden sink and slider to deck with steps to

  Stacy Levey William Raveis-New York, LLC

  100 Devoe 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 $2,071,092

  Not Listed For Sale

  1 Round Hill Rd, Chappaqua, NY 10514

  • 4 Beds
  • 3 Baths
  • 3,164 Sq Ft
  • Built 1963

  1 Round Hill Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 52 Days On Market

  Last Listing Agent Elaine Wasserman Houlihan Lawrence Inc.
• 

  $1,530,000

  Sold Sep 12, 2025

  31 Wynnewood Rd, Chappaqua, NY 10514

  • 4 Beds
  • 3 Baths
  • 2,420 Sq Ft
  • Built 1928

  Last Sold Summary

  • 22% Above List Price
  • $632/SF
  • 9 Days On Market

  Current Estimated Value $1,582,787

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  31 Wynnewood Rd, Chappaqua, NY 10514
• 

  Est $1,705,456

  Not Listed For Sale

  23 Round Hill Rd, Chappaqua, NY 10514

  • 5 Beds
  • 3.5 Baths
  • 3,230 Sq Ft
  • Built 1964

  23 Round Hill Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Michael Levy eXp Realty
• 

  $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
• 

  Est $2,147,576

  Not Listed For Sale

  2 Sunset Dr, Chappaqua, NY 10514

  • 4 Beds
  • 6 Baths
  • 5,474 Sq Ft
  • Built 1986

  2 Sunset Dr, Chappaqua, NY 10514

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC
• 

  $1,780,000

  Sold Dec 22, 2025

  56 Annandale Rd, Chappaqua, NY 10514

  • 4 Beds
  • 4.5 Baths
  • 4,543 Sq Ft
  • Built 2006

  Last Sold Summary

  • 1% Below List Price
  • $392/SF
  • 16 Days On Market

  Current Estimated Value $1,921,171

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

  56 Annandale Rd, Chappaqua, NY 10514
• 

  Est $1,563,149

  Not Listed For Sale

  12 Seven Bridges Rd, Chappaqua, NY 10514

  • 3 Beds
  • 2.5 Baths
  • 2,543 Sq Ft
  • Built 1950

  12 Seven Bridges Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Brendan Preston Houlihan Lawrence Inc.
• 

  $2,486,000

  Sold Aug 04, 2026

  17 Byram Meadows Rd, Chappaqua, NY 10514

  • 4 Beds
  • 4.5 Baths
  • 6,640 Sq Ft
  • Built 1999

  Last Sold Summary

  • 4% Below List Price
  • $374/SF
  • 99 Days On Market

  Current Estimated Value $2,443,150

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  17 Byram Meadows Rd, Chappaqua, NY 10514
• 

  Est $1,322,950

  Not Listed For Sale

  610 Quaker Rd, Chappaqua, NY 10514

  • 3 Beds
  • 2 Baths
  • 2,022 Sq Ft
  • Built 1954

  610 Quaker Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Igor Krasnoperov Rising Star Realty
• 

  $2,450,000

  Sold Jun 09, 2026

  5 Morning View Ct, Chappaqua, NY 10514

  • 4 Beds
  • 5 Baths
  • 5,767 Sq Ft
  • Built 2012

  Last Sold Summary

  • 26% Above List Price
  • $425/SF
  • 5 Days On Market

  Current Estimated Value $2,301,210

  Last Listing Agent Sari Shaw Compass Greater NY, LLC

  5 Morning View Ct, Chappaqua, NY 10514
• 

  Est $1,125,853

  Not Listed For Sale

  595 Quaker Rd, Chappaqua, NY 10514

  • 3 Beds
  • 3 Baths
  • 2,114 Sq Ft
  • Built 1953

  595 Quaker Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 84 Days On Market

  Last Listing Agent Brendan Preston Houlihan Lawrence Inc.
• 

  $1,630,000

  Sold Jun 15, 2026

  114 Old Lyme Rd, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 2,460 Sq Ft
  • Built 1977

  Last Sold Summary

  • 25% Above List Price
  • $663/SF
  • 6 Days On Market

  Current Estimated Value $1,623,784

  Last Listing Agent Sari Shaw Compass Greater NY, LLC

  114 Old Lyme Rd, Chappaqua, NY 10514
• 

  Est $2,208,975

  Not Listed For Sale

  2 Cedar Ln, Chappaqua, NY 10514

  • 5 Beds
  • 3.5 Baths
  • 4,462 Sq Ft
  • Built 1963

  2 Cedar Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Francie Malina Compass Greater NY, LLC
• 

  $1,375,000

  Sold Apr 20, 2026

  111 Seven Bridges Rd, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 2,069 Sq Ft
  • Built 1961

  Last Sold Summary

  • 15% Above List Price
  • $665/SF
  • 32 Days On Market

  Current Estimated Value $1,365,777

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

  111 Seven Bridges Rd, Chappaqua, NY 10514
• 

  Est $1,406,167

  Not Listed For Sale

  1283 Hardscrabble Rd, Chappaqua, NY 10514

  • 3 Beds
  • 2 Baths
  • 2,830 Sq Ft
  • Built 1820

  1283 Hardscrabble Rd, Chappaqua, NY 10514

  Last Sold Summary

  • 94 Days On Market

  Last Listing Agent Sari Shaw Compass Greater NY, LLC
• 

  $2,375,000

  Sold Jun 12, 2026

  24 North Way, Chappaqua, NY 10514

  • 3 Beds
  • 3.5 Baths
  • 3,960 Sq Ft
  • Built 1986

  Last Sold Summary

  • 3% Above List Price
  • $600/SF
  • 7 Days On Market

  Current Estimated Value $2,384,793

  Last Listing Agent Pamela Akin Douglas Elliman Real Estate

  24 North Way, Chappaqua, NY 10514
• 

  Est $3,178,142

  Not Listed For Sale

  76 Valley Ln, Chappaqua, NY 10514

  • 5 Beds
  • 5.5 Baths
  • 6,177 Sq Ft
  • Built 1987

  76 Valley Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 158 Days On Market

  Last Listing Agent Harriet Libov Houlihan Lawrence Inc.
• 

  $2,551,201

  Sold May 15, 2026

  0 Gray Rock Ln Unit KEY943867, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 4,500 Sq Ft
  • Built 2026

  Last Sold Summary

  • 29% Above List Price
  • $567/SF
  • 88 Days On Market

  Last Listing Agent Rachel Lacoste Houlihan Lawrence Inc.

  0 Gray Rock Ln Unit KEY943867, Chappaqua, NY 10514
• 

  Est $1,874,587

  Not Listed For Sale

  20 Suzanne Ln, Chappaqua, NY 10514

  • 4 Beds
  • 3.5 Baths
  • 3,307 Sq Ft
  • Built 1965

  20 Suzanne Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent MaryAnn Bayer Compass Greater NY, LLC
• 

  $1,600,000

  Sold Dec 12, 2025

  27 Deepwood Hill, Chappaqua, NY 10514

  • 3 Beds
  • 2.5 Baths
  • 2,830 Sq Ft
  • Built 1950

  Last Sold Summary

  • 14% Above List Price
  • $565/SF
  • 35 Days On Market

  Current Estimated Value $1,542,333

  Last Listing Agent Brendan Preston Houlihan Lawrence Inc.

  27 Deepwood Hill, Chappaqua, NY 10514
• 

  Est $2,619,238

  Not Listed For Sale

  95 Valley Ln, Chappaqua, NY 10514

  • 5 Beds
  • 5 Baths
  • 5,570 Sq Ft
  • Built 1979

  95 Valley Ln, Chappaqua, NY 10514

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Deena Bouchier Compass Greater NY, LLC
• 

  $1,850,000

  Sold Jun 01, 2026

  21 Kitchawan Dr, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 3,956 Sq Ft
  • Built 1922

  Last Sold Summary

  • 16% Above List Price
  • $468/SF
  • 13 Days On Market

  Current Estimated Value $1,817,515

  Last Listing Agent Jennifer Harris Compass Greater NY, LLC

  21 Kitchawan Dr, Chappaqua, NY 10514
• 

  Est $1,519,517

  Not Listed For Sale

  24 Hilltop Dr, Chappaqua, NY 10514

  • 3 Beds
  • 3 Baths
  • 3,186 Sq Ft
  • Built 1964

  24 Hilltop Dr, Chappaqua, NY 10514

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Kile Boga-Ibric Houlihan Lawrence Inc.
• 

  $1,850,000

  Sold Sep 02, 2025

  42 Cross Ridge Rd, Chappaqua, NY 10514

  • 3 Beds
  • 3 Baths
  • 3,102 Sq Ft
  • Built 1959

  Last Sold Summary

  • 35% Above List Price
  • $596/SF
  • 7 Days On Market

  Current Estimated Value $1,870,448

  Last Listing Agent Pamela Akin Douglas Elliman Real Estate

  42 Cross Ridge Rd, Chappaqua, NY 10514
• 

  Est $1,495,740

  Not Listed For Sale

  20 Hilltop Dr, Chappaqua, NY 10514

  • 4 Beds
  • 2.5 Baths
  • 2,762 Sq Ft
  • Built 1966

  20 Hilltop Dr, Chappaqua, NY 10514

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Keri Cipriano William Raveis Real Estate
• 

  $1,290,000

  Sold May 22, 2026

  80 Roaring Brook Rd, Chappaqua, NY 10514

  • 3 Beds
  • 3 Baths
  • 3,421 Sq Ft
  • Built 1954

  Last Sold Summary

  • $377/SF
  • 20 Days On Market

  Current Estimated Value $1,317,394

  Last Listing Agent Mark Okamoto Houlihan Lawrence Inc.

  80 Roaring Brook Rd, Chappaqua, NY 10514

Showing Results 121 - 160, Page 4 of 18