9,208

Winchester, MA Homes

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  • /42

    $1,330,000 Sold Aug 21, 2025

    14 Hillside Ave, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,605 Sq Ft
    • Built 1870

    Last Sold Summary

    • 19% Below List Price
    • $511/SF
    • 73 Days On Market

    Current Estimated Value $1,416,297

    Last Listing Agent Seeme Moreira Coldwell Banker Realty - Lexington

    14 Hillside Ave, Winchester, MA 01890
    • /35

      Est $3,191,660 Not Listed For Sale

      59 Bacon St, Winchester, MA 01890

      • 5 Beds
      • 5.5 Baths
      • 5,981 Sq Ft
      • Built 2023
      59 Bacon St, Winchester, MA 01890

      Last Sold Summary

      • 6% Above List Price
      • $502/SF
      • 22 Days On Market
      • Last Sold Price $3,000,000
      • Nov 07, 2024

      Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

  • /42

    $2,750,000 Sold Apr 03, 2026

    19 Town Way, Winchester, MA 01890

    • 5 Beds
    • 5.5 Baths
    • 5,257 Sq Ft
    • Built 2025

    Last Sold Summary

    • 8% Below List Price
    • $523/SF
    • 105 Days On Market

    Current Estimated Value $2,757,269

    Last Listing Agent Philip Vita Compass

    19 Town Way, Winchester, MA 01890
    • /42

      Est $2,029,877 Not Listed For Sale

      2 Fairfield Place, Winchester, MA 01890

      • 5 Beds
      • 2.5 Baths
      • 3,746 Sq Ft
      • Built 2005
      2 Fairfield Place, Winchester, MA 01890

      Last Sold Summary

      • 7% Above List Price
      • $507/SF
      • 6 Days On Market
      • Last Sold Price $1,900,000
      • Oct 11, 2024

      Last Listing Agent Kim Covino Compass

  • /2

    $1,875,000 Sold Mar 06, 2026

    5 Squire Rd, Winchester, MA 01890

    • 6 Beds
    • 3.5 Baths
    • 4,696 Sq Ft
    • Built 1958

    Last Sold Summary

    • 1% Below List Price
    • $399/SF
    • 13 Days On Market

    Current Estimated Value $1,889,471

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    5 Squire Rd, Winchester, MA 01890
    • /38

      Est $670,257 Not Listed For Sale

      50 Lake St Unit I, Winchester, MA 01890

      • 2 Beds
      • 1.5 Baths
      • 1,461 Sq Ft
      • Built 1976
      50 Lake St Unit I, Winchester, MA 01890

      Last Sold Summary

      • 1% Above List Price
      • $452/SF
      • 35 Days On Market
      • Last Sold Price $661,000
      • Oct 15, 2024

      Last Listing Agent Diane Plunkett Plunkett Properties

  • /11

    $1,269,000 Sold Jun 04, 2025

    158 Swanton St Unit 160, Winchester, MA 01890

    • 3 Beds
    • 3.5 Baths
    • 2,136 Sq Ft
    • Built 2025

    Last Sold Summary

    • $594/SF
    • 1 Day On Market

    Current Estimated Value $1,285,356

    Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    158 Swanton St Unit 160, Winchester, MA 01890
    • /42

      Est $713,948 Not Listed For Sale

      50 Lake St Unit H, Winchester, MA 01890

      • 3 Beds
      • 2.5 Baths
      • 1,407 Sq Ft
      • Built 1976
      50 Lake St Unit H, Winchester, MA 01890

      Last Sold Summary

      • 6% Above List Price
      • $480/SF
      • 5 Days On Market
      • Last Sold Price $675,000
      • May 15, 2023

      Last Listing Agent Rosemary Kelleher Laer Realty

  • /38

    $940,000 Sold Dec 23, 2025

    446 Highland Ave, Winchester, MA 01890

    • 2 Beds
    • 1.5 Baths
    • 2,033 Sq Ft
    • Built 1926

    Last Sold Summary

    • 6% Below List Price
    • $462/SF
    • 14 Days On Market

    Current Estimated Value $1,045,271

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    446 Highland Ave, Winchester, MA 01890
    • /24

      Est $679,365 Not Listed For Sale

      50 Lake St Unit D, Winchester, MA 01890

      • 2 Beds
      • 3 Baths
      • 1,265 Sq Ft
      • Built 1976
      50 Lake St Unit D, Winchester, MA 01890

      Last Sold Summary

      • 7% Above List Price
      • $502/SF
      • 9 Days On Market
      • Last Sold Price $635,000
      • Aug 28, 2023

      Last Listing Agent Sheri O'Connor Plunkett Properties

  • /39

    $3,599,000 Sold Nov 20, 2025

    5 Stratford Rd, Winchester, MA 01890

    • 6 Beds
    • 4.5 Baths
    • 5,876 Sq Ft
    • Built 1870

    Last Sold Summary

    • $612/SF
    • 27 Days On Market

    Current Estimated Value $3,572,203

    Last Listing Agent Kim Covino Compass

    5 Stratford Rd, Winchester, MA 01890
    • /31

      Est $1,057,918 Not Listed For Sale

      47 Clark St Unit 49, Winchester, MA 01890

      • 6 Beds
      • 2.5 Baths
      • 2,170 Sq Ft
      • Built 1890
      47 Clark St Unit 49, Winchester, MA 01890

      Last Sold Summary

      • 13% Above List Price
      • $430/SF
      • 4 Days On Market
      • Last Sold Price $932,700
      • May 24, 2024

      Last Listing Agent Kristi Connors - Taylor Coldwell Banker Realty - Lexington

  • /42

    $2,175,000 Sold Jan 16, 2026

    19 Gershon Way Unit 1, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 3,953 Sq Ft
    • Built 2020

    Last Sold Summary

    • 5% Below List Price
    • $550/SF
    • 19 Days On Market

    Last Listing Agent Philip Vita Compass

    19 Gershon Way Unit 1, Winchester, MA 01890
    • /38

      Est $986,207 Not Listed For Sale

      46 Clark St, Winchester, MA 01890

      • 4 Beds
      • 1 Bath
      • 1,616 Sq Ft
      • Built 1921
      46 Clark St, Winchester, MA 01890

      Last Sold Summary

      • 25% Above List Price
      • $489/SF
      • 6 Days On Market
      • Last Sold Price $790,000
      • May 03, 2024

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

  • /42

    $1,187,000 Sold Jun 18, 2025

    44 Forest St, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 1,906 Sq Ft
    • Built 1926

    Last Sold Summary

    • 1% Below List Price
    • $623/SF
    • 12 Days On Market

    Current Estimated Value $1,199,273

    Last Listing Agent Kim Covino Compass

    44 Forest St, Winchester, MA 01890
    • /28

      Est $1,020,156 Not Listed For Sale

      63 Middlesex St, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 1,614 Sq Ft
      • Built 1948
      63 Middlesex St, Winchester, MA 01890

      Last Sold Summary

      • 11% Above List Price
      • $567/SF
      • 4 Days On Market
      • Last Sold Price $915,000
      • Aug 29, 2024

      Last Listing Agent HMW Team HMW Real Estate, LLC

  • /42

    $2,862,500 Sold Oct 10, 2025

    54 Wedgemere Ave, Winchester, MA 01890

    • 6 Beds
    • 3.5 Baths
    • 5,238 Sq Ft
    • Built 1915

    Last Sold Summary

    • 4% Below List Price
    • $546/SF
    • 6 Days On Market

    Current Estimated Value $2,883,696

    Last Listing Agent Kim Covino Compass

    54 Wedgemere Ave, Winchester, MA 01890
    • /34

      Est $1,476,848 Not Listed For Sale

      78 Middlesex St, Winchester, MA 01890

      • 3 Beds
      • 2.5 Baths
      • 2,650 Sq Ft
      • Built 1900
      78 Middlesex St, Winchester, MA 01890

      Last Sold Summary

      • 7% Below List Price
      • $596/SF
      • 26 Days On Market
      • Last Sold Price $1,580,000
      • Nov 29, 2024

      Last Listing Agent Marjie and Phil Gibson Sotheby's International Realty

  • /32

    $1,865,000 Sold Dec 30, 2025

    1 Copley St, Winchester, MA 01890

    • 7 Beds
    • 2.5 Baths
    • 2,998 Sq Ft
    • Built 1913

    Last Sold Summary

    • 8% Above List Price
    • $622/SF
    • 4 Days On Market

    Current Estimated Value $1,900,282

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

    1 Copley St, Winchester, MA 01890
    • /18

      Est $1,155,101 Not Listed For Sale

      44 Middlesex St Unit 46, Winchester, MA 01890

      • 5 Beds
      • 2 Baths
      • 2,392 Sq Ft
      • Built 1900
      44 Middlesex St Unit 46, Winchester, MA 01890

      Last Sold Summary

      • 12% Above List Price
      • $431/SF
      • 39 Days On Market
      • Last Sold Price $1,030,000
      • Aug 10, 2023

      Last Listing Agent Kim Covino Compass

  • /39

    $1,400,000 Sold Jul 14, 2025

    20 Fletcher St Unit 20, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,282 Sq Ft
    • Built 2025

    Last Sold Summary

    • 3% Below List Price
    • $613/SF
    • 38 Days On Market

    Last Listing Agent Kim Covino Compass

    20 Fletcher St Unit 20, Winchester, MA 01890
    • /41

      Est $1,182,869 Not Listed For Sale

      61 Lake St, Winchester, MA 01890

      • 4 Beds
      • 1.5 Baths
      • 1,985 Sq Ft
      • Built 1931
      61 Lake St, Winchester, MA 01890

      Last Sold Summary

      • 11% Above List Price
      • $539/SF
      • 10 Days On Market
      • Last Sold Price $1,070,000
      • Apr 16, 2024

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

  • /30

    $1,025,000 Sold Apr 02, 2026

    353-355 Washington St, Winchester, MA 01890

    • 6 Beds
    • 2 Baths
    • 2,605 Sq Ft
    • Built 1926

    Last Sold Summary

    • $393/SF
    • 4 Days On Market

    Last Listing Agent Julie Gibson Gibson Sotheby's International Realty

    353-355 Washington St, Winchester, MA 01890
    • /31

      Est $727,666 Not Listed For Sale

      400 Cross St Unit 401, Winchester, MA 01890

      • 2 Beds
      • 2.5 Baths
      • 1,523 Sq Ft
      • Built 2004
      400 Cross St Unit 401, Winchester, MA 01890

      Last Sold Summary

      • 4% Below List Price
      • $496/SF
      • 17 Days On Market
      • Last Sold Price $755,000
      • Jul 05, 2024

      Last Listing Agent Montivista Real Estate Group eXp Realty

  • /38

    $1,924,000 Sold Jul 10, 2025

    5 Hastings Rd, Winchester, MA 01890

    • 4 Beds
    • 4 Baths
    • 4,195 Sq Ft
    • Built 1995

    Last Sold Summary

    • 1% Above List Price
    • $459/SF
    • 4 Days On Market

    Current Estimated Value $2,000,481

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    5 Hastings Rd, Winchester, MA 01890
    • /39

      Est $738,272 Not Listed For Sale

      400 Cross St Unit 304, Winchester, MA 01890

      • 2 Beds
      • 2.5 Baths
      • 1,366 Sq Ft
      • Built 2004
      400 Cross St Unit 304, Winchester, MA 01890

      Last Sold Summary

      • 5% Above List Price
      • $517/SF
      • 5 Days On Market
      • Last Sold Price $706,000
      • Aug 28, 2023

      Last Listing Agent Susan Bridge J. Barrett & Company

  • /30

    $1,185,000 Sold Oct 08, 2025

    5 Emerson Ct, Winchester, MA 01890

    • 3 Beds
    • 3.5 Baths
    • 2,000 Sq Ft
    • Built 1870

    Last Sold Summary

    • 1% Below List Price
    • $592/SF
    • 5 Days On Market

    Current Estimated Value $1,184,035

    Last Listing Agent Elaine Song Coldwell Banker Realty - Lexington

    5 Emerson Ct, Winchester, MA 01890
    • /31

      Est $720,781 Not Listed For Sale

      400 Cross St Unit 201, Winchester, MA 01890

      • 2 Beds
      • 2.5 Baths
      • 1,346 Sq Ft
      • Built 2004
      400 Cross St Unit 201, Winchester, MA 01890

      Last Sold Summary

      • 1% Below List Price
      • $542/SF
      • 15 Days On Market
      • Last Sold Price $730,000
      • Sep 03, 2024

      Last Listing Agent Lucille Murray Gibson Sotheby's International Realty

  • /36

    $1,250,000 Sold Nov 14, 2025

    35 Harvard St, Winchester, MA 01890

    • 5 Beds
    • 2 Baths
    • 1,706 Sq Ft
    • Built 1880

    Last Sold Summary

    • 4% Below List Price
    • $733/SF
    • 17 Days On Market

    Current Estimated Value $1,239,521

    Last Listing Agent Joanne Mulkerin J. Mulkerin Realty

    35 Harvard St, Winchester, MA 01890
    • /41

      Est $988,455 Not Listed For Sale

      22 Water St, Winchester, MA 01890

      • 4 Beds
      • 2 Baths
      • 1,932 Sq Ft
      • Built 1912
      22 Water St, Winchester, MA 01890

      Last Sold Summary

      • 12% Above List Price
      • $458/SF
      • 5 Days On Market
      • Last Sold Price $885,000
      • Oct 05, 2024

      Last Listing Agent Kristin Weekley Leading Edge Real Estate

  • /31

    $1,355,000 Sold Nov 20, 2025

    4 Sargent Rd, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,865 Sq Ft
    • Built 1945

    Last Sold Summary

    • 3% Below List Price
    • $473/SF
    • 10 Days On Market

    Current Estimated Value $1,380,773

    Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    4 Sargent Rd, Winchester, MA 01890
    • /24

      Est $975,104 Not Listed For Sale

      25 Hemingway St, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 1,890 Sq Ft
      • Built 1969
      25 Hemingway St, Winchester, MA 01890

      Last Sold Summary

      • 1% Above List Price
      • $509/SF
      • 21 Days On Market
      • Last Sold Price $962,000
      • Dec 18, 2024

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • /40

    $1,375,000 Sold Mar 20, 2026

    19 Cox Rd, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 2,351 Sq Ft
    • Built 1956

    Last Sold Summary

    • 8% Below List Price
    • $585/SF
    • 7 Days On Market

    Current Estimated Value $1,454,042

    Last Listing Agent Kim Covino Compass

    19 Cox Rd, Winchester, MA 01890
    • /24

      Est $1,097,891 Not Listed For Sale

      253 Pond St, Winchester, MA 01890

      • 3 Beds
      • 1.5 Baths
      • 1,788 Sq Ft
      • Built 1952
      253 Pond St, Winchester, MA 01890

      Last Sold Summary

      • 2% Above List Price
      • $601/SF
      • 69 Days On Market
      • Last Sold Price $1,075,000
      • Sep 26, 2024

      Last Listing Agent Ida Bianco Coldwell Banker Realty - Lexington

  • /42

    $1,325,000 Sold Apr 22, 2026

    6 Marchant Rd, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,153 Sq Ft
    • Built 1938

    Last Sold Summary

    • 2% Below List Price
    • $615/SF
    • 20 Days On Market

    Current Estimated Value $1,340,201

    Last Listing Agent Kim Covino Compass

    6 Marchant Rd, Winchester, MA 01890
    • /31

      Est $1,164,235 Not Listed For Sale

      102 Sylvester Ave, Winchester, MA 01890

      • 3 Beds
      • 2.5 Baths
      • 1,968 Sq Ft
      • Built 1925
      102 Sylvester Ave, Winchester, MA 01890

      Last Sold Summary

      • 4% Above List Price
      • $569/SF
      • 5 Days On Market
      • Last Sold Price $1,120,000
      • Jul 26, 2024

      Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

  • /36

    $749,900 Sold Jun 13, 2025

    7 Conant Rd Unit 34, Winchester, MA 01890

    • 2 Beds
    • 2 Baths
    • 1,545 Sq Ft
    • Built 1999

    Last Sold Summary

    • $485/SF
    • 8 Days On Market

    Current Estimated Value $751,705

    Last Listing Agent Melanie Lentini Leading Edge Real Estate

    7 Conant Rd Unit 34, Winchester, MA 01890
    • /42

      Est $984,973 Not Listed For Sale

      9 Upland Rd, Winchester, MA 01890

      • 3 Beds
      • 2.5 Baths
      • 1,468 Sq Ft
      • Built 1929
      9 Upland Rd, Winchester, MA 01890

      Last Sold Summary

      • 4% Above List Price
      • $644/SF
      • 45 Days On Market
      • Last Sold Price $945,000
      • Nov 30, 2023

      Last Listing Agent Anne Spry Barrett Sotheby's International Realty

  • /36

    $1,950,000 Sold Sep 25, 2025

    4 Fieldstone Dr, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 4,378 Sq Ft
    • Built 1987

    Last Sold Summary

    • 11% Below List Price
    • $445/SF
    • 40 Days On Market

    Current Estimated Value $1,986,896

    Last Listing Agent Wenli Zheng Fairview Partners International LLC

    4 Fieldstone Dr, Winchester, MA 01890
    • /41

      Est $1,042,016 Not Listed For Sale

      7 Upland Rd, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 1,810 Sq Ft
      • Built 1929
      7 Upland Rd, Winchester, MA 01890

      Last Sold Summary

      • 17% Above List Price
      • $492/SF
      • 17 Days On Market
      • Last Sold Price $890,000
      • Feb 20, 2024

      Last Listing Agent Anne Spry Barrett Sotheby's International Realty

Showing Results 401 - 440, Page 11 of 18

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