9,200

Winchester, MA Homes

Section Image
    • 50 Lake St Unit D, Winchester, MA 01890
      50 Lake St Unit D, Winchester, MA 01890
      50 Lake St Unit D, Winchester, MA 01890
      /24

      Est $703,607

      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

      • 9 Days On Market

      Last Listing Agent Sheri O'Connor Plunkett Properties

  • 147 Highland Ave, Winchester, MA 01890
    147 Highland Ave, Winchester, MA 01890
    147 Highland Ave, Winchester, MA 01890
    /37

    $1,200,000

    Sold Sep 25, 2025

    147 Highland Ave, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 1,884 Sq Ft
    • Built 1919

    Last Sold Summary

    • 14% Below List Price
    • $637/SF
    • 103 Days On Market

    Current Estimated Value $1,270,212

    Last Listing Agent Kim Covino Compass

    147 Highland Ave, Winchester, MA 01890
    • 47 Clark St Unit 49, Winchester, MA 01890
      47 Clark St Unit 49, Winchester, MA 01890
      47 Clark St Unit 49, Winchester, MA 01890
      /31

      Est $1,150,083

      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

      • 4 Days On Market

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

  • 10 Blossom Hill Rd, Winchester, MA 01890
    10 Blossom Hill Rd, Winchester, MA 01890
    10 Blossom Hill Rd, Winchester, MA 01890
    /42

    $1,678,500

    Sold Sep 25, 2025

    10 Blossom Hill Rd, Winchester, MA 01890

    • 4 Beds
    • 2 Baths
    • 3,838 Sq Ft
    • Built 1951

    Last Sold Summary

    • 1% Below List Price
    • $437/SF
    • 10 Days On Market

    Current Estimated Value $1,726,567

    Last Listing Agent Stephen DeConto Cameron Real Estate Group

    10 Blossom Hill Rd, Winchester, MA 01890
    • 32 Clark St, Winchester, MA 01890
      32 Clark St, Winchester, MA 01890
      32 Clark St, Winchester, MA 01890
      /33

      Est $822,220

      Not Listed For Sale

      32 Clark St, Winchester, MA 01890

      • 2 Beds
      • 1.5 Baths
      • 1,326 Sq Ft
      • Built 1890
      32 Clark St, Winchester, MA 01890

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Rodrigo Serrano Leading Edge Real Estate

  • 105 Thornberry Rd, Winchester, MA 01890
    105 Thornberry Rd, Winchester, MA 01890
    /2

    $1,899,000

    Sold Jul 09, 2026

    105 Thornberry Rd, Winchester, MA 01890

    • 5 Beds
    • 2.5 Baths
    • 3,278 Sq Ft
    • Built 1971

    Last Sold Summary

    • $579/SF
    • 10 Days On Market

    Current Estimated Value $1,881,845

    Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    105 Thornberry Rd, Winchester, MA 01890
    • 63 Middlesex St, Winchester, MA 01890
      63 Middlesex St, Winchester, MA 01890
      63 Middlesex St, Winchester, MA 01890
      /28

      Est $996,696

      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

      • 4 Days On Market

      Last Listing Agent HMW Team HMW Real Estate, LLC

  • 200 Swanton St Unit 538, Winchester, MA 01890
    200 Swanton St Unit 538, Winchester, MA 01890
    200 Swanton St Unit 538, Winchester, MA 01890
    /13

    $250,000

    Sold Jun 22, 2026

    200 Swanton St Unit 538, Winchester, MA 01890

    • 1 Bath
    • 394 Sq Ft
    • Built 1966

    Last Sold Summary

    • 13% Below List Price
    • $635/SF
    • 36 Days On Market

    Current Estimated Value $256,546

    Last Listing Agent Michael Masci North Atlantic Realty Group

    200 Swanton St Unit 538, Winchester, MA 01890
    • 78 Middlesex St, Winchester, MA 01890
      78 Middlesex St, Winchester, MA 01890
      78 Middlesex St, Winchester, MA 01890
      /34

      Est $1,449,361

      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

      • 26 Days On Market

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

  • 12 Canterbury Rd, Winchester, MA 01890
    12 Canterbury Rd, Winchester, MA 01890
    12 Canterbury Rd, Winchester, MA 01890
    /33

    $1,325,000

    Sold Dec 22, 2025

    12 Canterbury Rd, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 1,942 Sq Ft
    • Built 1942

    Last Sold Summary

    • 10% Above List Price
    • $682/SF
    • 9 Days On Market

    Current Estimated Value $1,379,566

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

    12 Canterbury Rd, Winchester, MA 01890
    • 44 Middlesex St Unit 46, Winchester, MA 01890
      44 Middlesex St Unit 46, Winchester, MA 01890
      44 Middlesex St Unit 46, Winchester, MA 01890
      /18

      Est $1,156,862

      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

      • 39 Days On Market

      Last Listing Agent Kim Covino Compass

  • 9 Pilgrim Dr, Winchester, MA 01890
    9 Pilgrim Dr, Winchester, MA 01890
    9 Pilgrim Dr, Winchester, MA 01890
    /42

    $1,725,000

    Sold Sep 19, 2025

    9 Pilgrim Dr, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,541 Sq Ft
    • Built 1960

    Last Sold Summary

    • 8% Above List Price
    • $679/SF
    • 6 Days On Market

    Current Estimated Value $1,740,024

    Last Listing Agent McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

    9 Pilgrim Dr, Winchester, MA 01890
    • 61 Lake St, Winchester, MA 01890
      61 Lake St, Winchester, MA 01890
      61 Lake St, Winchester, MA 01890
      /41

      Est $1,188,442

      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

      • 10 Days On Market

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

  • 56 Yale St, Winchester, MA 01890
    56 Yale St, Winchester, MA 01890
    56 Yale St, Winchester, MA 01890
    /42

    $2,830,000

    Sold Jun 23, 2026

    56 Yale St, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 4,792 Sq Ft
    • Built 1923

    Last Sold Summary

    • 1% Above List Price
    • $591/SF
    • 7 Days On Market

    Current Estimated Value $2,771,786

    Last Listing Agent Patricia Fitzgerald Brad Hutchinson Real Estate

    56 Yale St, Winchester, MA 01890
    • 400 Cross St Unit 401, Winchester, MA 01890
      400 Cross St Unit 401, Winchester, MA 01890
      400 Cross St Unit 401, Winchester, MA 01890
      /31

      Est $746,101

      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

      • 17 Days On Market

      Last Listing Agent Montivista Real Estate Group eXp Realty LLC - Corporate Office

  • 162 Forest St, Winchester, MA 01890
    162 Forest St, Winchester, MA 01890
    162 Forest St, Winchester, MA 01890
    /33

    $1,280,000

    Sold Oct 03, 2025

    162 Forest St, Winchester, MA 01890

    • 4 Beds
    • 1.5 Baths
    • 1,900 Sq Ft
    • Built 1930

    Last Sold Summary

    • 2% Above List Price
    • $674/SF
    • 9 Days On Market

    Current Estimated Value $1,312,699

    Last Listing Agent Paul Cirignano The Synergy Group

    162 Forest St, Winchester, MA 01890
    • 400 Cross St Unit 304, Winchester, MA 01890
      400 Cross St Unit 304, Winchester, MA 01890
      400 Cross St Unit 304, Winchester, MA 01890
      /39

      Est $728,459

      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 Days On Market

      Last Listing Agent Susan Bridge J. Barrett & Company

  • 4 Aricia Ln, Winchester, MA 01890
    4 Aricia Ln, Winchester, MA 01890
    4 Aricia Ln, Winchester, MA 01890
    /42

    $1,656,000

    Sold Oct 31, 2025

    4 Aricia Ln, Winchester, MA 01890

    • 4 Beds
    • 5 Baths
    • 5,361 Sq Ft
    • Built 1984

    Last Sold Summary

    • 13% Below List Price
    • $309/SF
    • 88 Days On Market

    Current Estimated Value $1,825,836

    Last Listing Agent The McLaren D'Agostino Team Compass

    4 Aricia Ln, Winchester, MA 01890
    • 400 Cross St Unit 201, Winchester, MA 01890
      400 Cross St Unit 201, Winchester, MA 01890
      400 Cross St Unit 201, Winchester, MA 01890
      /31

      Est $736,491

      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

      • 15 Days On Market

      Last Listing Agent Lucille Murray Gibson Sotheby's International Realty

  • 16 Park Ave Unit 2, Winchester, MA 01890
    16 Park Ave Unit 2, Winchester, MA 01890
    16 Park Ave Unit 2, Winchester, MA 01890
    /32

    $999,999

    Sold Nov 21, 2025

    16 Park Ave Unit 2, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 1,756 Sq Ft
    • Built 1915

    Last Sold Summary

    • 5% Above List Price
    • $569/SF
    • 9 Days On Market

    Current Estimated Value $1,019,418

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

    16 Park Ave Unit 2, Winchester, MA 01890
    • 22 Water St, Winchester, MA 01890
      22 Water St, Winchester, MA 01890
      22 Water St, Winchester, MA 01890
      /41

      Est $953,432

      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

      • 5 Days On Market

      Last Listing Agent Kristin Weekley Leading Edge Real Estate

  • 89 Main St, Winchester, MA 01890
    89 Main St, Winchester, MA 01890
    89 Main St, Winchester, MA 01890
    /41

    $1,150,000

    Sold Nov 14, 2025

    89 Main St, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,648 Sq Ft
    • Built 1932

    Last Sold Summary

    • 2% Above List Price
    • $434/SF
    • 8 Days On Market

    Current Estimated Value $1,214,450

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    89 Main St, Winchester, MA 01890
    • 25 Hemingway St, Winchester, MA 01890
      25 Hemingway St, Winchester, MA 01890
      25 Hemingway St, Winchester, MA 01890
      /24

      Est $1,014,701

      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

      • 21 Days On Market

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • 3 Socrates Way, Winchester, MA 01890
    3 Socrates Way, Winchester, MA 01890
    3 Socrates Way, Winchester, MA 01890
    /33

    $1,240,000

    Sold Aug 20, 2025

    3 Socrates Way, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,570 Sq Ft
    • Built 1966

    Last Sold Summary

    • 5% Below List Price
    • $482/SF
    • 9 Days On Market

    Current Estimated Value $1,353,271

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

    3 Socrates Way, Winchester, MA 01890
    • 253 Pond St, Winchester, MA 01890
      253 Pond St, Winchester, MA 01890
      253 Pond St, Winchester, MA 01890
      /24

      Est $1,144,107

      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

      • 69 Days On Market

      Last Listing Agent Ida Bianco Coldwell Banker Realty - Lexington

  • 19 Town Way, Winchester, MA 01890
    19 Town Way, Winchester, MA 01890
    19 Town Way, Winchester, MA 01890
    /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 $2,636,040

    Last Listing Agent Philip Vita Compass

    19 Town Way, Winchester, MA 01890
    • 102 Sylvester Ave, Winchester, MA 01890
      102 Sylvester Ave, Winchester, MA 01890
      102 Sylvester Ave, Winchester, MA 01890
      /31

      Est $1,168,288

      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

      • 5 Days On Market

      Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

  • 104 Wendell St, Winchester, MA 01890
    104 Wendell St, Winchester, MA 01890
    104 Wendell St, Winchester, MA 01890
    /42

    $1,100,000

    Sold May 28, 2026

    104 Wendell St, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 1,675 Sq Ft
    • Built 1951

    Last Sold Summary

    • 12% Above List Price
    • $657/SF
    • 6 Days On Market

    Current Estimated Value $1,043,545

    Last Listing Agent Kim Covino Compass

    104 Wendell St, Winchester, MA 01890
    • 9 Upland Rd, Winchester, MA 01890
      9 Upland Rd, Winchester, MA 01890
      9 Upland Rd, Winchester, MA 01890
      /42

      Est $981,571

      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

      • 45 Days On Market

      Last Listing Agent Anne Spry Barrett Sotheby's International Realty

  • 5 Squire Rd, Winchester, MA 01890
    5 Squire Rd, Winchester, MA 01890
    /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 $1,902,031

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    5 Squire Rd, Winchester, MA 01890
    • 7 Upland Rd, Winchester, MA 01890
      7 Upland Rd, Winchester, MA 01890
      7 Upland Rd, Winchester, MA 01890
      /41

      Est $1,073,901

      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 Days On Market

      Last Listing Agent Anne Spry Barrett Sotheby's International Realty

  • 446 Highland Ave, Winchester, MA 01890
    446 Highland Ave, Winchester, MA 01890
    446 Highland Ave, Winchester, MA 01890
    /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 $1,069,063

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    446 Highland Ave, Winchester, MA 01890
    • 18 Hemingway St, Winchester, MA 01890
      18 Hemingway St, Winchester, MA 01890
      18 Hemingway St, Winchester, MA 01890
      /32

      Est $1,352,710

      Not Listed For Sale

      18 Hemingway St, Winchester, MA 01890

      • 5 Beds
      • 3.5 Baths
      • 2,137 Sq Ft
      • Built 2015
      18 Hemingway St, Winchester, MA 01890

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Julia Xie Keller Williams Realty-Merrimack

  • 5 Stratford Rd, Winchester, MA 01890
    5 Stratford Rd, Winchester, MA 01890
    5 Stratford Rd, Winchester, MA 01890
    /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 $3,603,326

    Last Listing Agent Kim Covino Compass

    5 Stratford Rd, Winchester, MA 01890
    • 5 Sylvester Ct, Winchester, MA 01890
      5 Sylvester Ct, Winchester, MA 01890
      5 Sylvester Ct, Winchester, MA 01890
      /37

      Est $1,342,545

      Not Listed For Sale

      5 Sylvester Ct, Winchester, MA 01890

      • 4 Beds
      • 2 Baths
      • 2,280 Sq Ft
      • Built 1963
      5 Sylvester Ct, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Philip Vita Compass

  • 19 Gershon Way Unit 1, Winchester, MA 01890
    19 Gershon Way Unit 1, Winchester, MA 01890
    19 Gershon Way Unit 1, Winchester, MA 01890
    /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
    • 79 Sylvester Ave, Winchester, MA 01890
      79 Sylvester Ave, Winchester, MA 01890
      79 Sylvester Ave, Winchester, MA 01890
      /31

      Est $938,127

      Not Listed For Sale

      79 Sylvester Ave, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 1,469 Sq Ft
      • Built 1928
      79 Sylvester Ave, Winchester, MA 01890

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Anne Spry Barrett Sotheby's International Realty

  • 237 Swanton St, Winchester, MA 01890
    237 Swanton St, Winchester, MA 01890
    237 Swanton St, Winchester, MA 01890
    /34

    $1,850,000

    Sold May 29, 2026

    237 Swanton St, Winchester, MA 01890

    • 5 Beds
    • 4 Baths
    • 4,334 Sq Ft
    • Built 2020

    Last Sold Summary

    • 7% Below List Price
    • $427/SF
    • 23 Days On Market

    Current Estimated Value $1,910,898

    Last Listing Agent Kim Covino Compass

    237 Swanton St, Winchester, MA 01890
    • 83 Canal St Unit 85, Winchester, MA 01890
      83 Canal St Unit 85, Winchester, MA 01890
      83 Canal St Unit 85, Winchester, MA 01890
      /39

      Not Listed For Sale

      83 Canal St Unit 85, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 2,300 Sq Ft
      • Built 2017
      83 Canal St Unit 85, Winchester, MA 01890

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Mary O'Hagan Barrett Sotheby's International Realty

  • 54 Wedgemere Ave, Winchester, MA 01890
    54 Wedgemere Ave, Winchester, MA 01890
    54 Wedgemere Ave, Winchester, MA 01890
    /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 $2,985,846

    Last Listing Agent Kim Covino Compass

    54 Wedgemere Ave, Winchester, MA 01890

Showing Results 401 - 440, Page 11 of 18

Massachusetts Middlesex County

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