296

Recently Sold Winchester, MA Homes

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  • /34

    $1,392,500

    Sold Jan 09, 2026

    53 Bacon St, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,865 Sq Ft
    • Built 1959

    Last Sold Summary

    • 7% Below List Price
    • $486/SF
    • 37 Days On Market

    Current Estimated Value $1,488,915

    Last Listing Agent Taleen Chiofaro Leading Edge Real Estate

    53 Bacon St, Winchester, MA 01890
  • /32

    $1,825,000

    Sold Aug 03, 2026

    10 Graystone Cir Unit 10, Winchester, MA 01890

    • 2 Beds
    • 3.5 Baths
    • 3,874 Sq Ft
    • Built 2010

    Last Sold Summary

    • 1% Above List Price
    • $471/SF
    • 6 Days On Market

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    10 Graystone Cir Unit 10, Winchester, MA 01890
  • /28

    $1,160,000

    Sold Aug 27, 2026

    52 Salem St Unit 52, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,004 Sq Ft
    • Built 1880

    Last Sold Summary

    • 1% Above List Price
    • $579/SF
    • 7 Days On Market

    Last Listing Agent Michael Rauseo Better Homes and Gardens Real Estate - The Shanahan Group

    52 Salem St Unit 52, Winchester, MA 01890
  • /42

    $1,250,000

    Sold May 29, 2026

    87 Wendell St, Winchester, MA 01890

    • 4 Beds
    • 2 Baths
    • 2,046 Sq Ft
    • Built 1914

    Last Sold Summary

    • 4% Below List Price
    • $611/SF
    • 8 Days On Market

    Current Estimated Value $1,243,542

    Last Listing Agent Kim Covino Compass

    87 Wendell St, Winchester, MA 01890
  • /41

    $3,900,000

    Sold Oct 24, 2025

    12 Ledgewood Rd, Winchester, MA 01890

    • 5 Beds
    • 4.5 Baths
    • 5,069 Sq Ft
    • Built 2016

    Last Sold Summary

    • 1% Above List Price
    • $769/SF
    • 2 Days On Market

    Current Estimated Value $3,766,474

    Last Listing Agent Leigh Ventura Compass

    12 Ledgewood Rd, Winchester, MA 01890
  • /33

    $1,600,000

    Sold Oct 10, 2025

    10 Olde Lyme Rd, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 3,478 Sq Ft
    • Built 1960

    Last Sold Summary

    • 18% Below List Price
    • $460/SF
    • 57 Days On Market

    Current Estimated Value $1,693,868

    Last Listing Agent Darryl Brian RE/MAX Bentley's

    10 Olde Lyme Rd, Winchester, MA 01890
  • /25

    $955,225

    Sold Jan 27, 2026

    41 Squire Rd, Winchester, MA 01890

    • 4 Beds
    • 1.5 Baths
    • 2,162 Sq Ft
    • Built 1958

    Last Sold Summary

    • 3% Below List Price
    • $442/SF
    • 33 Days On Market

    Current Estimated Value $1,061,192

    Last Listing Agent William Cordts Coldwell Banker Realty - Waltham

    41 Squire Rd, Winchester, MA 01890
  • /26

    $340,000

    Sold Feb 02, 2026

    200 Swanton St Unit 630, Winchester, MA 01890

    • 1 Bed
    • 1 Bath
    • 613 Sq Ft
    • Built 1966

    Last Sold Summary

    • 1% Below List Price
    • $555/SF
    • 15 Days On Market

    Current Estimated Value $341,443

    Last Listing Agent Angela Hirtle Lyv Realty

    200 Swanton St Unit 630, Winchester, MA 01890
  • /40

    $1,850,000

    Sold Mar 26, 2026

    20 Grove Place, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 3,294 Sq Ft
    • Built 1910

    Last Sold Summary

    • 1% Below List Price
    • $562/SF
    • 40 Days On Market

    Current Estimated Value $1,854,870

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    20 Grove Place, Winchester, MA 01890
  • /40

    $2,450,000

    Sold Jan 09, 2026

    29 Shepard Ct, Winchester, MA 01890

    • 6 Beds
    • 5 Baths
    • 4,594 Sq Ft
    • Built 2025

    Last Sold Summary

    • 2% Above List Price
    • $533/SF
    • 6 Days On Market

    Current Estimated Value $2,337,157

    Last Listing Agent Pirani & Wile Group Gibson Sotheby's International Realty

    29 Shepard Ct, Winchester, MA 01890
  • /42

    $2,142,000

    Sold Sep 22, 2026

    42 Wildwood St, Winchester, MA 01890

    • 7 Beds
    • 4.5 Baths
    • 4,930 Sq Ft
    • Built 1880

    Last Sold Summary

    • 7% Below List Price
    • $434/SF
    • 36 Days On Market

    Current Estimated Value $2,245,867

    Last Listing Agent Carolyn Walsh Better Homes and Gardens Real Estate - The Shanahan Group

    42 Wildwood St, Winchester, MA 01890
  • /35

    $2,600,000

    Sold Jul 15, 2026

    47 Yale St, Winchester, MA 01890

    • 6 Beds
    • 5 Baths
    • 4,540 Sq Ft
    • Built 1920

    Last Sold Summary

    • 5% Below List Price
    • $573/SF
    • 29 Days On Market

    Current Estimated Value $2,630,731

    Last Listing Agent Molly Nolan Byrne Coldwell Banker Realty - Belmont

    47 Yale St, Winchester, MA 01890
  • /42

    $1,900,000

    Sold Oct 17, 2025

    2 Lagrange St, Winchester, MA 01890

    • 7 Beds
    • 2.5 Baths
    • 3,413 Sq Ft
    • Built 1890

    Last Sold Summary

    • 5% Below List Price
    • $557/SF
    • 12 Days On Market

    Current Estimated Value $2,045,742

    Last Listing Agent Alison Lules-Cuccio Don Baker Real Estate

    2 Lagrange St, Winchester, MA 01890
  • /34

    $1,015,000

    Sold Dec 01, 2025

    9 Sylvester Ct, Winchester, MA 01890

    • 4 Beds
    • 1.5 Baths
    • 2,001 Sq Ft
    • Built 1963

    Last Sold Summary

    • 2% Above List Price
    • $507/SF
    • 9 Days On Market

    Current Estimated Value $1,060,820

    Last Listing Agent Kim Covino Compass

    9 Sylvester Ct, Winchester, MA 01890
  • /19

    $878,000

    Sold Sep 26, 2025

    17 Baldwin St, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 1,672 Sq Ft
    • Built 1890

    Last Sold Summary

    • 2% Below List Price
    • $525/SF
    • 2 Days On Market

    Current Estimated Value $953,495

    Last Listing Agent Dennis Oliveira JDS Realty Group

    17 Baldwin St, Winchester, MA 01890
  • /42

    $1,574,500

    Sold Mar 30, 2026

    263 Highland Ave, Winchester, MA 01890

    • 4 Beds
    • 4 Baths
    • 3,343 Sq Ft
    • Built 1894

    Last Sold Summary

    • 7% Below List Price
    • $471/SF
    • 84 Days On Market

    Current Estimated Value $1,656,599

    Last Listing Agent Seeme Moreira Coldwell Banker Realty - Lexington

    263 Highland Ave, Winchester, MA 01890
  • /33

    $680,000

    Sold Mar 16, 2026

    7 Conant Rd Unit 33, Winchester, MA 01890

    • 2 Beds
    • 2 Baths
    • 1,532 Sq Ft
    • Built 1999

    Last Sold Summary

    • 3% Below List Price
    • $444/SF
    • 23 Days On Market

    Current Estimated Value $688,948

    Last Listing Agent Pirani & Wile Group Gibson Sotheby's International Realty

    7 Conant Rd Unit 33, Winchester, MA 01890
  • /42

    $1,218,000

    Sold May 20, 2026

    40 Englewood Rd, Winchester, MA 01890

    • 4 Beds
    • 2 Baths
    • 1,841 Sq Ft
    • Built 1939

    Last Sold Summary

    • 11% Above List Price
    • $662/SF
    • 6 Days On Market

    Current Estimated Value $1,199,883

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    40 Englewood Rd, Winchester, MA 01890
  • /34

    $1,020,000

    Sold Jun 05, 2026

    149 Horn Pond Brook Rd, Winchester, MA 01890

    • 5 Beds
    • 2 Baths
    • 2,331 Sq Ft
    • Built 1954

    Last Sold Summary

    • 21% Below List Price
    • $438/SF
    • 67 Days On Market

    Current Estimated Value $1,134,921

    Last Listing Agent Nancy McLaughlin Redfin Corp.

    149 Horn Pond Brook Rd, Winchester, MA 01890
  • /34

    $1,200,000

    Sold Dec 08, 2025

    36 Elmwood Ave Unit 2, Winchester, MA 01890

    • 2 Beds
    • 2 Baths
    • 1,342 Sq Ft
    • Built 2021

    Last Sold Summary

    • 2% Below List Price
    • $894/SF
    • 6 Days On Market

    Current Estimated Value $1,195,755

    Last Listing Agent Charles Ginsberg Coldwell Banker Realty - Lexington

    36 Elmwood Ave Unit 2, Winchester, MA 01890
  • /41

    $2,549,000

    Sold Jun 29, 2026

    10 Viking Rd, Winchester, MA 01890

    • 4 Beds
    • 4 Baths
    • 5,674 Sq Ft
    • Built 1979

    Last Sold Summary

    • 2% Below List Price
    • $449/SF
    • 2 Days On Market

    Current Estimated Value $2,521,521

    Last Listing Agent Kim Covino Compass

    10 Viking Rd, Winchester, MA 01890
  • /39

    $1,350,000

    Sold Sep 02, 2026

    11 Williams Cir, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,392 Sq Ft
    • Built 2001

    Last Sold Summary

    • 17% Above List Price
    • $564/SF
    • 5 Days On Market

    Current Estimated Value $1,242,827

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    11 Williams Cir, Winchester, MA 01890
  • /41

    $1,200,000

    Sold Aug 17, 2026

    52 Middlesex St Unit 52, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,303 Sq Ft
    • Built 1920

    Last Sold Summary

    • $521/SF
    • 8 Days On Market

    Last Listing Agent The North Star Group Keller Williams Realty Evolution

    52 Middlesex St Unit 52, Winchester, MA 01890
  • /16

    $899,000

    Sold Nov 25, 2025

    60 Harvard St, Winchester, MA 01890

    • 4 Beds
    • 3 Baths
    • 1,860 Sq Ft
    • Built 1914

    Last Sold Summary

    • 27% Below List Price
    • $483/SF
    • 93 Days On Market

    Current Estimated Value $911,487

    Last Listing Agent Mark Krasnyansky eXp Realty LLC

    60 Harvard St, Winchester, MA 01890
  • /35

    $1,660,000

    Sold Aug 07, 2026

    10 Farrow St, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 2,768 Sq Ft
    • Built 1955

    Last Sold Summary

    • 1% Above List Price
    • $600/SF
    • 6 Days On Market

    Current Estimated Value $1,644,353

    Last Listing Agent Collin Bray Century 21 Cityside

    10 Farrow St, Winchester, MA 01890
  • /37

    $1,450,000

    Sold Jun 12, 2026

    34 Robinhood Rd, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 3,380 Sq Ft
    • Built 1959

    Last Sold Summary

    • 9% Below List Price
    • $429/SF
    • 23 Days On Market

    Current Estimated Value $1,500,976

    Last Listing Agent Janet Halloran RE/MAX Real Estate Center

    34 Robinhood Rd, Winchester, MA 01890
  • /24

    $1,070,000

    Sold May 20, 2026

    198 Pond St, Winchester, MA 01890

    • 4 Beds
    • 1.5 Baths
    • 1,917 Sq Ft
    • Built 1947

    Last Sold Summary

    • 7% Above List Price
    • $558/SF
    • 5 Days On Market

    Current Estimated Value $1,066,220

    Last Listing Agent The Murphy Group Lexington William Raveis R.E. & Home Services

    198 Pond St, Winchester, MA 01890
  • /40

    $1,607,000

    Sold Jun 01, 2026

    6 Oakland Cir, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 3,298 Sq Ft
    • Built 1953

    Last Sold Summary

    • 4% Above List Price
    • $487/SF
    • 7 Days On Market

    Current Estimated Value $1,588,429

    Last Listing Agent Seeme Moreira Coldwell Banker Realty - Lexington

    6 Oakland Cir, Winchester, MA 01890
  • /42

    $2,400,000

    Sold Jun 30, 2026

    216 Highland Ave, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 4,822 Sq Ft
    • Built 1902

    Last Sold Summary

    • 4% Above List Price
    • $498/SF
    • 5 Days On Market

    Current Estimated Value $2,266,475

    Last Listing Agent Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group

    216 Highland Ave, Winchester, MA 01890
  • /42

    $2,200,000

    Sold May 05, 2026

    10 Edgehill Rd, Winchester, MA 01890

    • 7 Beds
    • 3.5 Baths
    • 3,926 Sq Ft
    • Built 1910

    Last Sold Summary

    • 2% Below List Price
    • $560/SF
    • 9 Days On Market

    Current Estimated Value $2,144,135

    Last Listing Agent Lynne Russo Better Homes and Gardens Real Estate - The Shanahan Group

    10 Edgehill Rd, Winchester, MA 01890
  • /41

    $1,290,000

    Sold Jan 29, 2026

    46-48 Swanton St, Winchester, MA 01890

    • 6 Beds
    • 3.5 Baths
    • 3,233 Sq Ft
    • Built 1887

    Last Sold Summary

    • 17% Above List Price
    • $399/SF
    • 6 Days On Market

    Last Listing Agent Leeman & Gately Compass

    46-48 Swanton St, Winchester, MA 01890
  • /37

    $1,850,000

    Sold Apr 23, 2026

    58 Jefferson Rd, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,910 Sq Ft
    • Built 1984

    Last Sold Summary

    • 3% Above List Price
    • $636/SF
    • 5 Days On Market

    Current Estimated Value $1,840,018

    Last Listing Agent Stephanie Macfarland Wilson Wolfe Real Estate

    58 Jefferson Rd, Winchester, MA 01890
  • /32

    $620,000

    Sold Jul 30, 2026

    14 Bradford Rd Unit 14, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 1,168 Sq Ft
    • Built 1963

    Last Sold Summary

    • 1% Below List Price
    • $531/SF
    • 3 Days On Market

    Last Listing Agent Janet Wu Cook Keller Williams Elite

    14 Bradford Rd Unit 14, Winchester, MA 01890
  • /33

    $681,888

    Sold Mar 25, 2026

    9 Charles Rd, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 973 Sq Ft
    • Built 1963

    Last Sold Summary

    • 14% Above List Price
    • $701/SF
    • 6 Days On Market

    Current Estimated Value $673,575

    Last Listing Agent Kim Covino Compass

    9 Charles Rd, Winchester, MA 01890
  • /42

    $1,399,000

    Sold Jun 30, 2026

    71 Sargent Rd, Winchester, MA 01890

    • 3 Beds
    • 3.5 Baths
    • 2,936 Sq Ft
    • Built 1985

    Last Sold Summary

    • $476/SF
    • 9 Days On Market

    Current Estimated Value $1,416,085

    Last Listing Agent Bob Bittelari Berkshire Hathaway HomeServices Commonwealth Real Estate

    71 Sargent Rd, Winchester, MA 01890
  • /35

    $1,060,000

    Sold Jun 09, 2026

    62 Richardson St, Winchester, MA 01890

    • 5 Beds
    • 2.5 Baths
    • 2,849 Sq Ft
    • Built 1870

    Last Sold Summary

    • $372/SF
    • 7 Days On Market

    Current Estimated Value $1,224,062

    Last Listing Agent Frank Ventresca Strategy Street

    62 Richardson St, Winchester, MA 01890
  • /42

    $1,857,000

    Sold Sep 15, 2026

    2 Olde Lyme Rd, Winchester, MA 01890

    • 3 Beds
    • 3.5 Baths
    • 2,513 Sq Ft
    • Built 1960

    Last Sold Summary

    • 9% Above List Price
    • $739/SF
    • 8 Days On Market

    Current Estimated Value $1,640,948

    Last Listing Agent Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group

    2 Olde Lyme Rd, Winchester, MA 01890
  • /33

    $1,470,000

    Sold Mar 25, 2026

    2 Canterbury Rd, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,370 Sq Ft
    • Built 1940

    Last Sold Summary

    • 5% Above List Price
    • $620/SF
    • 8 Days On Market

    Current Estimated Value $1,469,135

    Last Listing Agent Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group

    2 Canterbury Rd, Winchester, MA 01890
  • /40

    $2,250,000

    Sold Dec 11, 2025

    14 Grant Rd, Winchester, MA 01890

    • 6 Beds
    • 4.5 Baths
    • 4,200 Sq Ft
    • Built 2025

    Last Sold Summary

    • 4% Below List Price
    • $536/SF
    • 26 Days On Market

    Current Estimated Value $2,257,909

    Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    14 Grant Rd, Winchester, MA 01890
  • /13

    $3,200,000

    Sold May 13, 2026

    39 Town Way, Winchester, MA 01890

    • 6 Beds
    • 7 Baths
    • 5,709 Sq Ft
    • Built 2025

    Last Sold Summary

    • $561/SF
    • 21 Days On Market

    Last Listing Agent Kim Covino Compass

    39 Town Way, Winchester, MA 01890

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