Recently Sold Lewisboro, NY Homes

• 

  $1,275,000 Sold Oct 16, 2025

  29 Oscaleta Rd, South Salem, NY 10590

  • 3 Beds
  • 2 Baths
  • 2,076 Sq Ft
  • Built 1953

  Last Sold Summary

  • 15% Below List Price
  • $614/SF
  • 151 Days On Market

  Current Estimated Value $1,271,741

  Last Listing Agent Susan Stillman Houlihan Lawrence Inc.

  29 Oscaleta Rd, South Salem, NY 10590
• 

  $720,000 Sold Jul 31, 2025

  12 Truesdale Lake Dr, South Salem, NY 10590

  • 4 Beds
  • 2 Baths
  • 1,875 Sq Ft
  • Built 1971

  Last Sold Summary

  • 11% Above List Price
  • $384/SF
  • 44 Days On Market

  Current Estimated Value $776,238

  Last Listing Agent Eileen McGrath Douglas Elliman Real Estate

  12 Truesdale Lake Dr, South Salem, NY 10590
• 

  $788,000 Sold May 16, 2025

  28 Lakeview Pass, Katonah, NY 10536

  • 2 Beds
  • 1.5 Baths
  • 1,587 Sq Ft
  • Built 1930

  Last Sold Summary

  • 7% Above List Price
  • $497/SF
  • 12 Days On Market

  Current Estimated Value $821,612

  Last Listing Agent Cheryl Neuburger Ginnel Real Estate

  28 Lakeview Pass, Katonah, NY 10536
• 

  $1,255,000 Sold Mar 14, 2025

  149 Ridgefield Ave, South Salem, NY 10590

  • 5 Beds
  • 5 Baths
  • 5,896 Sq Ft
  • Built 1988

  Last Sold Summary

  • 13% Below List Price
  • $213/SF
  • 95 Days On Market

  Current Estimated Value $1,378,600

  Last Listing Agent Mark Boyland Keller Williams Realty Partner

  149 Ridgefield Ave, South Salem, NY 10590
• 

  $1,075,000 Sold Sep 03, 2025

  309 N Salem Rd, Waccabuc, NY 10597

  • 4 Beds
  • 2.5 Baths
  • 3,180 Sq Ft
  • Built 1977

  Last Sold Summary

  • 2% Below List Price
  • $338/SF
  • 29 Days On Market

  Current Estimated Value $1,130,067

  Last Listing Agent Mary Stoll

  309 N Salem Rd, Waccabuc, NY 10597
• 

  $537,500 Sold Dec 22, 2025

  29 Quincy Ct, Goldens Bridge, NY 10526

  • 2 Beds
  • 1.5 Baths
  • 2,274 Sq Ft
  • Built 1974

  Last Sold Summary

  • 7% Below List Price
  • $236/SF
  • 163 Days On Market

  Last Listing Agent Randy Calano Keller Williams Realty Partner

  29 Quincy Ct, Goldens Bridge, NY 10526
• 

  $1,444,500 Sold Dec 12, 2025

  7 Hilltop Rd, Waccabuc, NY 10597

  • 4 Beds
  • 4.5 Baths
  • 3,192 Sq Ft
  • Built 1985

  Last Sold Summary

  • 4% Above List Price
  • $453/SF
  • 15 Days On Market

  Last Listing Agent Rita Carrozza

  7 Hilltop Rd, Waccabuc, NY 10597
• 

  $900,000 Sold Feb 18, 2025

  18 Redcoat Ln, Waccabuc, NY 10597

  • 4 Beds
  • 2.5 Baths
  • 2,521 Sq Ft
  • Built 1969

  Last Sold Summary

  • 10% Below List Price
  • $357/SF
  • 30 Days On Market

  Current Estimated Value $1,029,363

  Last Listing Agent Mary Dowdle Ginnel Real Estate

  18 Redcoat Ln, Waccabuc, NY 10597
• 

  $910,000 Sold Mar 31, 2025

  7 Out Post Rd, Katonah, NY 10536

  • 3 Beds
  • 3 Baths
  • 1,668 Sq Ft
  • Built 1966

  Last Sold Summary

  • 2% Above List Price
  • $546/SF
  • 27 Days On Market

  Current Estimated Value $989,146

  Last Listing Agent Tricia Farin Real Broker NY LLC

  7 Out Post Rd, Katonah, NY 10536
• 

  $755,000 Sold Apr 30, 2025

  10 Deer Run Rd, South Salem, NY 10590

  • 4 Beds
  • 2 Baths
  • 1,894 Sq Ft
  • Built 1963

  Last Sold Summary

  • 12% Above List Price
  • $399/SF
  • 13 Days On Market

  Current Estimated Value $794,688

  Last Listing Agent Lindsay Lafreniere William Raveis-New York LLC

  10 Deer Run Rd, South Salem, NY 10590
• 

  $1,395,000 Sold Sep 17, 2025

  18 Gideon Reynolds Rd, Cross River, NY 10518

  • 4 Beds
  • 4.5 Baths
  • 5,194 Sq Ft
  • Built 1995

  Last Sold Summary

  • $269/SF
  • 27 Days On Market

  Current Estimated Value $1,437,909

  Last Listing Agent Anne-Marie Nordgren Coldwell Banker Realty

  18 Gideon Reynolds Rd, Cross River, NY 10518
• 

  $750,000 Sold Dec 09, 2025

  64 Ridgeland Rd, South Salem, NY 10590

  • 2 Beds
  • 2 Baths
  • 1,299 Sq Ft
  • Built 1926

  Last Sold Summary

  • 9% Above List Price
  • $577/SF
  • 22 Days On Market

  Last Listing Agent James Avery Coldwell Banker Realty

  64 Ridgeland Rd, South Salem, NY 10590
• 

  $1,002,710 Sold Aug 01, 2025

  5 Canaan Cir, South Salem, NY 10590

  • 4 Beds
  • 2.5 Baths
  • 2,246 Sq Ft
  • Built 1985

  Last Sold Summary

  • 6% Above List Price
  • $446/SF
  • 21 Days On Market

  Current Estimated Value $997,521

  Last Listing Agent Kenneth Sobel Julia B Fee Sothebys Int. Rlty

  5 Canaan Cir, South Salem, NY 10590
• 

  $1,443,500 Sold Oct 23, 2025

  2 Shoshone Dr, Katonah, NY 10536

  • 4 Beds
  • 2.5 Baths
  • 3,376 Sq Ft
  • Built 1983

  Last Sold Summary

  • 13% Above List Price
  • $428/SF
  • 33 Days On Market

  Current Estimated Value $1,402,963

  Last Listing Agent Wendy Loring William Raveis-New York LLC

  2 Shoshone Dr, Katonah, NY 10536
• 

  $2,250,000 Sold Jul 24, 2025

  168 Todd Rd, Katonah, NY 10536

  • 3 Beds
  • 2.5 Baths
  • 2,955 Sq Ft
  • Built 1938

  Last Sold Summary

  • 29% Above List Price
  • $761/SF
  • 10 Days On Market

  Current Estimated Value $2,211,914

  Last Listing Agent Kristine Blake Sotheby's International Realty

  168 Todd Rd, Katonah, NY 10536
• 

  $1,199,000 Sold Jul 25, 2025

  3 Scenic Dr, South Salem, NY 10590

  • 4 Beds
  • 3.5 Baths
  • 3,079 Sq Ft
  • Built 1986

  Last Sold Summary

  • $389/SF
  • 24 Days On Market

  Current Estimated Value $1,191,510

  Last Listing Agent Michael Vasquez eXp Realty

  3 Scenic Dr, South Salem, NY 10590
• 

  $489,000 Sold Dec 18, 2025

  8 Hemlock Rd, South Salem, NY 10590

  • 2 Beds
  • 1.5 Baths
  • 1,530 Sq Ft
  • Built 1990

  Last Sold Summary

  • $320/SF
  • 31 Days On Market

  Last Listing Agent Wendy Loring William Raveis-New York LLC

  8 Hemlock Rd, South Salem, NY 10590
• 

  $1,400,000 Sold Mar 21, 2025

  48 Mead St, Waccabuc, NY 10597

  • 3 Beds
  • 2.5 Baths
  • 2,800 Sq Ft
  • Built 1945

  Last Sold Summary

  • 6% Below List Price
  • $500/SF
  • 43 Days On Market

  Current Estimated Value $1,630,044

  Last Listing Agent Mary Dowdle Ginnel Real Estate

  48 Mead St, Waccabuc, NY 10597
• 

  $1,200,000 Sold Aug 25, 2025

  8 Upland Ct, South Salem, NY 10590

  • 4 Beds
  • 4 Baths
  • 3,502 Sq Ft
  • Built 1985

  Last Sold Summary

  • $343/SF
  • 26 Days On Market

  Current Estimated Value $1,213,393

  Last Listing Agent Luke Joachim Redfin Real Estate

  8 Upland Ct, South Salem, NY 10590
• 

  $720,000 Sold Dec 23, 2025

  37 East St, South Salem, NY 10590

  • 2 Beds
  • 1 Bath
  • 1,068 Sq Ft
  • Built 1948

  Last Sold Summary

  • 5% Above List Price
  • $674/SF
  • 23 Days On Market

  Last Listing Agent Brianna Carvalho Compass Greater NY, LLC

  37 East St, South Salem, NY 10590
• 

  $660,000 Sold Sep 09, 2025

  55 Winterberry Cir, Cross River, NY 10518

  • 3 Beds
  • 2.5 Baths
  • 1,713 Sq Ft
  • Built 1987

  Last Sold Summary

  • 5% Above List Price
  • $385/SF
  • 26 Days On Market

  Current Estimated Value $651,803

  Last Listing Agent Patricia Hinkley Coldwell Banker Realty

  55 Winterberry Cir, Cross River, NY 10518
• 

  $550,000 Sold Jun 02, 2025

  28 West Rd, South Salem, NY 10590

  • 2 Beds
  • 1 Bath
  • 1,176 Sq Ft
  • Built 1921

  Last Sold Summary

  • 10% Above List Price
  • $468/SF
  • 20 Days On Market

  Current Estimated Value $552,717

  Last Listing Agent Giancarlo Pecora eXp Realty

  28 West Rd, South Salem, NY 10590
• 

  $1,075,000 Sold Aug 27, 2025

  31 Tri Brook Dr, South Salem, NY 10590

  • 4 Beds
  • 3.5 Baths
  • 2,556 Sq Ft
  • Built 1978

  Last Sold Summary

  • 2% Below List Price
  • $421/SF
  • 40 Days On Market

  Current Estimated Value $1,083,529

  Last Listing Agent Susan Mason

  31 Tri Brook Dr, South Salem, NY 10590
• 

  $1,170,000 Sold Sep 18, 2025

  7 Hunt Farm Rd, Waccabuc, NY 10597

  • 3 Beds
  • 3.5 Baths
  • 3,548 Sq Ft
  • Built 1987

  Last Sold Summary

  • 2% Below List Price
  • $330/SF
  • 29 Days On Market

  Current Estimated Value $1,198,306

  Last Listing Agent Susan Berman

  7 Hunt Farm Rd, Waccabuc, NY 10597
• 

  $385,000 Sold Aug 28, 2025

  6 Hemlock Rd, South Salem, NY 10590

  • 3 Beds
  • 1 Bath
  • 1,400 Sq Ft
  • Built 1928

  Last Sold Summary

  • 16% Below List Price
  • $275/SF
  • 214 Days On Market

  Current Estimated Value $422,652

  Last Listing Agent Jonathan Gineo Jonathan D. Gineo

  6 Hemlock Rd, South Salem, NY 10590
• 

  $3,828,000 Sold Aug 07, 2025

  49 Mead St, Waccabuc, NY 10597

  • 4 Beds
  • 3.5 Baths
  • 4,224 Sq Ft
  • Built 1780

  Last Sold Summary

  • 1% Above List Price
  • $906/SF
  • 28 Days On Market

  Current Estimated Value $3,664,057

  Last Listing Agent Christine Byrne Ginnel Real Estate

  49 Mead St, Waccabuc, NY 10597
• 

  $2,250,000 Sold Apr 23, 2025

  696 Cross River Rd, Katonah, NY 10536

  • 5 Beds
  • 4.5 Baths
  • 6,000 Sq Ft
  • Built 2006

  Last Sold Summary

  • 4% Below List Price
  • $375/SF
  • 186 Days On Market

  Current Estimated Value $2,422,025

  Last Listing Agent Donna O'Connell Houlihan Lawrence Inc.

  696 Cross River Rd, Katonah, NY 10536
• 

  $665,000 Sold Jan 14, 2026

  123 Park Road Extension, Goldens Bridge, NY 10526

  • 2 Beds
  • 2.5 Baths
  • 1,880 Sq Ft
  • Built 1998

  Last Sold Summary

  • 2% Below List Price
  • $354/SF
  • 65 Days On Market

  Last Listing Agent Cheryl Neuburger Ginnel Real Estate

  123 Park Road Extension, Goldens Bridge, NY 10526
• 

  $1,575,000 Sold Dec 10, 2025

  831 Route 35, Cross River, NY 10518

  • 4 Beds
  • 1.5 Baths
  • 2,476 Sq Ft
  • Built 1930

  Last Sold Summary

  • 5% Above List Price
  • $636/SF
  • 28 Days On Market

  Last Listing Agent Mark Boyland Keller Williams Realty Partner

  831 Route 35, Cross River, NY 10518
• 

  $1,405,000 Sold Sep 29, 2025

  1090 Route 35, South Salem, NY 10590

  • 5 Beds
  • 5 Baths
  • 3,815 Sq Ft
  • Built 1780

  Last Sold Summary

  • 1% Above List Price
  • $368/SF
  • 19 Days On Market

  Current Estimated Value $1,445,564

  Last Listing Agent Stuart Emanuel Coldwell Banker Realty

  1090 Route 35, South Salem, NY 10590
• 

  $1,475,000 Sold Aug 22, 2025

  64 Lambert Ridge, Cross River, NY 10518

  • 5 Beds
  • 3 Baths
  • 4,882 Sq Ft
  • Built 1998

  Last Sold Summary

  • $302/SF
  • 17 Days On Market

  Current Estimated Value $1,502,533

  Last Listing Agent Wendy Loring William Raveis-New York LLC

  64 Lambert Ridge, Cross River, NY 10518
• 

  $1,510,000 Sold Jul 22, 2025

  9 Sullivan Rd, Goldens Bridge, NY 10526

  • 4 Beds
  • 4.5 Baths
  • 4,384 Sq Ft
  • Built 1996

  Last Sold Summary

  • 2% Above List Price
  • $344/SF
  • 28 Days On Market

  Current Estimated Value $1,561,639

  Last Listing Agent Donna Ornstein William Raveis-New York LLC

  9 Sullivan Rd, Goldens Bridge, NY 10526
• 

  $556,150 Sold Sep 30, 2025

  242 Deer Hill Unit 27242, South Salem, NY 10590

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 1988

  Last Sold Summary

  • 12% Above List Price
  • $428/SF
  • 32 Days On Market

  Current Estimated Value $545,900

  Last Listing Agent Mark Boyland Keller Williams Realty Partner

  242 Deer Hill Unit 27242, South Salem, NY 10590
• 

  $1,369,000 Sold Aug 13, 2025

  12 Five Ponds Dr, Waccabuc, NY 10597

  • 5 Beds
  • 3.5 Baths
  • 5,318 Sq Ft
  • Built 1987

  Last Sold Summary

  • 23% Below List Price
  • $257/SF
  • 58 Days On Market

  Current Estimated Value $1,434,085

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

  12 Five Ponds Dr, Waccabuc, NY 10597
• 

  $999,000 Sold Sep 09, 2025

  7 Main St, South Salem, NY 10590

  • 3 Beds
  • 2.5 Baths
  • 2,116 Sq Ft
  • Built 1750

  Last Sold Summary

  • 5% Below List Price
  • $472/SF
  • 64 Days On Market

  Current Estimated Value $1,010,888

  Last Listing Agent Michael Neeley William Raveis-New York LLC

  7 Main St, South Salem, NY 10590
• 

  $470,000 Sold Jan 17, 2026

  31 S Shore Dr, South Salem, NY 10590

  • 1 Bed
  • 1 Bath
  • 793 Sq Ft
  • Built 1920

  Last Sold Summary

  • 6% Below List Price
  • $593/SF
  • 46 Days On Market

  Last Listing Agent Maxwell Erni The Bridge Realty Group NY LLC

  31 S Shore Dr, South Salem, NY 10590
• 

  $475,000 Sold Jul 23, 2025

  73 Fox Run Unit 373, South Salem, NY 10590

  • 2 Beds
  • 1.5 Baths
  • 1,070 Sq Ft
  • Built 1981

  Last Sold Summary

  • 12% Above List Price
  • $444/SF
  • 11 Days On Market

  Current Estimated Value $457,234

  Last Listing Agent Cate Hegarty Compass Greater NY, LLC

  73 Fox Run Unit 373, South Salem, NY 10590
• 

  $1,300,000 Sold May 16, 2025

  25 Highview Rd, Pound Ridge, NY 10576

  • 4 Beds
  • 3.5 Baths
  • 3,552 Sq Ft
  • Built 1986

  Last Sold Summary

  • 10% Below List Price
  • $366/SF
  • 127 Days On Market

  Current Estimated Value $1,365,444

  Last Listing Agent Anthony DeBellis Douglas Elliman Real Estate

  25 Highview Rd, Pound Ridge, NY 10576
• 

  $1,350,000 Sold Jul 15, 2025

  98 Hack Green Rd, Pound Ridge, NY 10576

  • 4 Beds
  • 3.5 Baths
  • 3,134 Sq Ft
  • Built 1945

  Last Sold Summary

  • 13% Above List Price
  • $431/SF
  • 9 Days On Market

  Current Estimated Value $1,365,069

  Last Listing Agent Joanne Padawer Houlihan Lawrence Inc.

  98 Hack Green Rd, Pound Ridge, NY 10576
• 

  $1,100,000 Sold May 06, 2025

  92 Flat Rock Dr, Ridgefield, CT 06877

  • 5 Beds
  • 3.5 Baths
  • 3,128 Sq Ft
  • Built 1964

  Last Sold Summary

  • 11% Above List Price
  • $352/SF
  • 19 Days On Market

  Current Estimated Value $1,122,832

  Last Listing Agent Tim Dent Coldwell Banker Realty

  92 Flat Rock Dr, Ridgefield, CT 06877

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