9,202

Winchester, MA Homes

Section Image
  • 171 Swanton St Unit 12, Winchester, MA 01890
    171 Swanton St Unit 12, Winchester, MA 01890
    171 Swanton St Unit 12, Winchester, MA 01890
    /28

    $785,500

    Sold Aug 20, 2025

    171 Swanton St Unit 12, Winchester, MA 01890

    • 2 Beds
    • 2.5 Baths
    • 1,435 Sq Ft
    • Built 1984

    Last Sold Summary

    • 3% Above List Price
    • $547/SF
    • 8 Days On Market

    Current Estimated Value $797,572

    Last Listing Agent John and Maria Reilly JMR Real Estate Group LLC

    171 Swanton St Unit 12, Winchester, MA 01890
    • 48 Wedgemere Ave, Winchester, MA 01890
      48 Wedgemere Ave, Winchester, MA 01890
      48 Wedgemere Ave, Winchester, MA 01890
      /42

      Est $2,418,669

      Not Listed For Sale

      48 Wedgemere Ave, Winchester, MA 01890

      • 5 Beds
      • 4.5 Baths
      • 4,173 Sq Ft
      • Built 1914
      48 Wedgemere Ave, Winchester, MA 01890

      Last Sold Summary

      • 8 Days On Market

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

  • 77 Washington St, Winchester, MA 01890
    77 Washington St, Winchester, MA 01890
    77 Washington St, Winchester, MA 01890
    /31

    $1,700,000

    Sold Oct 16, 2025

    77 Washington St, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 2,718 Sq Ft
    • Built 1910

    Last Sold Summary

    • 6% Above List Price
    • $625/SF
    • 6 Days On Market

    Current Estimated Value $1,739,866

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    77 Washington St, Winchester, MA 01890
    • 51 Wedgemere Ave, Winchester, MA 01890
      51 Wedgemere Ave, Winchester, MA 01890
      51 Wedgemere Ave, Winchester, MA 01890
      /42

      Est $2,768,746

      Not Listed For Sale

      51 Wedgemere Ave, Winchester, MA 01890

      • 5 Beds
      • 5 Baths
      • 4,279 Sq Ft
      • Built 1914
      51 Wedgemere Ave, Winchester, MA 01890

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Kim Covino Compass

  • 666 Main St Unit 312, Winchester, MA 01890
    666 Main St Unit 312, Winchester, MA 01890
    /2

    $750,000

    Sold Feb 05, 2026

    666 Main St Unit 312, Winchester, MA 01890

    • 2 Beds
    • 2 Baths
    • 1,240 Sq Ft
    • Built 1982

    Last Sold Summary

    • 6% Below List Price
    • $605/SF
    • 0 Days On Market

    Current Estimated Value $758,308

    Last Listing Agent Walace Nogueira

    666 Main St Unit 312, Winchester, MA 01890
    • 3 Foxcroft Rd, Winchester, MA 01890
      3 Foxcroft Rd, Winchester, MA 01890
      3 Foxcroft Rd, Winchester, MA 01890
      /22

      Est $3,565,720

      Not Listed For Sale

      3 Foxcroft Rd, Winchester, MA 01890

      • 6 Beds
      • 5.5 Baths
      • 5,208 Sq Ft
      • Built 2025
      3 Foxcroft Rd, Winchester, MA 01890

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Kim Covino Compass

  • 211 Forest St, Winchester, MA 01890
    211 Forest St, Winchester, MA 01890
    211 Forest St, Winchester, MA 01890
    /41

    $2,125,000

    Sold Aug 04, 2026

    211 Forest St, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 3,474 Sq Ft
    • Built 1890

    Last Sold Summary

    • 3% Below List Price
    • $612/SF
    • 12 Days On Market

    Current Estimated Value $2,153,472

    Last Listing Agent Michael Gilbert Stuart St James, Inc.

    211 Forest St, Winchester, MA 01890
    • 64 Wildwood St, Winchester, MA 01890
      64 Wildwood St, Winchester, MA 01890
      64 Wildwood St, Winchester, MA 01890
      /42

      Est $2,794,891

      Not Listed For Sale

      64 Wildwood St, Winchester, MA 01890

      • 5 Beds
      • 4.5 Baths
      • 4,400 Sq Ft
      • Built 1917
      64 Wildwood St, Winchester, MA 01890

      Last Sold Summary

      • 67 Days On Market

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

  • 61 Westland Ave, Winchester, MA 01890
    61 Westland Ave, Winchester, MA 01890
    61 Westland Ave, Winchester, MA 01890
    /41

    $1,800,000

    Sold Feb 24, 2026

    61 Westland Ave, Winchester, MA 01890

    • 3 Beds
    • 3.5 Baths
    • 2,785 Sq Ft
    • Built 1952

    Last Sold Summary

    • 3% Above List Price
    • $646/SF
    • 6 Days On Market

    Current Estimated Value $1,711,175

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

    61 Westland Ave, Winchester, MA 01890
    • 49 Oxford St, Winchester, MA 01890
      49 Oxford St, Winchester, MA 01890
      49 Oxford St, Winchester, MA 01890
      /42

      Est $2,668,398

      Not Listed For Sale

      49 Oxford St, Winchester, MA 01890

      • 7 Beds
      • 3.5 Baths
      • 5,616 Sq Ft
      • Built 1910
      49 Oxford St, Winchester, MA 01890

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Kim Covino Compass

  • 303 Washington St, Winchester, MA 01890
    303 Washington St, Winchester, MA 01890
    303 Washington St, Winchester, MA 01890
    /42

    $1,367,500

    Sold Jul 24, 2026

    303 Washington St, Winchester, MA 01890

    • 6 Beds
    • 2 Baths
    • 5,047 Sq Ft
    • Built 1916

    Last Sold Summary

    • 1% Below List Price
    • $271/SF
    • 15 Days On Market

    Current Estimated Value $1,361,949

    Last Listing Agent Kim Covino Compass

    303 Washington St, Winchester, MA 01890
    • 19 Warren St, Winchester, MA 01890
      19 Warren St, Winchester, MA 01890
      19 Warren St, Winchester, MA 01890
      /42

      Est $1,828,571

      Not Listed For Sale

      19 Warren St, Winchester, MA 01890

      • 3 Beds
      • 3.5 Baths
      • 2,886 Sq Ft
      • Built 1911
      19 Warren St, Winchester, MA 01890

      Last Sold Summary

      • 7 Days On Market

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

  • 36 Middlesex St Unit 38, Winchester, MA 01890
    36 Middlesex St Unit 38, Winchester, MA 01890
    36 Middlesex St Unit 38, Winchester, MA 01890
    /32

    $1,380,000

    Sold Feb 26, 2026

    36 Middlesex St Unit 38, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 2,259 Sq Ft
    • Built 2020

    Last Sold Summary

    • 6% Above List Price
    • $611/SF
    • 6 Days On Market

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

    36 Middlesex St Unit 38, Winchester, MA 01890
    • 38 Cabot St, Winchester, MA 01890
      38 Cabot St, Winchester, MA 01890
      38 Cabot St, Winchester, MA 01890
      /24

      Est $2,383,809

      Not Listed For Sale

      38 Cabot St, Winchester, MA 01890

      • 5 Beds
      • 3.5 Baths
      • 3,516 Sq Ft
      • Built 1911
      38 Cabot St, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Joseph Castro Compass

  • 15 Englewood Rd, Winchester, MA 01890
    15 Englewood Rd, Winchester, MA 01890
    15 Englewood Rd, Winchester, MA 01890
    /29

    $1,425,000

    Sold May 07, 2026

    15 Englewood Rd, Winchester, MA 01890

    • 4 Beds
    • 3 Baths
    • 1,903 Sq Ft
    • Built 1928

    Last Sold Summary

    • 2% Above List Price
    • $749/SF
    • 4 Days On Market

    Current Estimated Value $1,414,288

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

    15 Englewood Rd, Winchester, MA 01890
    • 44 Cabot St, Winchester, MA 01890
      44 Cabot St, Winchester, MA 01890
      44 Cabot St, Winchester, MA 01890
      /42

      Est $2,451,737

      Not Listed For Sale

      44 Cabot St, Winchester, MA 01890

      • 4 Beds
      • 2 Baths
      • 3,691 Sq Ft
      • Built 1926
      44 Cabot St, Winchester, MA 01890

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • 89 Wildwood St, Winchester, MA 01890
    89 Wildwood St, Winchester, MA 01890
    89 Wildwood St, Winchester, MA 01890
    /37

    $2,200,000

    Sold Apr 16, 2026

    89 Wildwood St, Winchester, MA 01890

    • 7 Beds
    • 5.5 Baths
    • 4,929 Sq Ft
    • Built 1952

    Last Sold Summary

    • 4% Below List Price
    • $446/SF
    • 67 Days On Market

    Current Estimated Value $2,275,282

    Last Listing Agent George Sarkis Douglas Elliman Real Estate - The Sarkis Team

    89 Wildwood St, Winchester, MA 01890
    • 17 Harrison St, Winchester, MA 01890
      17 Harrison St, Winchester, MA 01890
      17 Harrison St, Winchester, MA 01890
      /42

      Est $2,452,744

      Not Listed For Sale

      17 Harrison St, Winchester, MA 01890

      • 5 Beds
      • 3.5 Baths
      • 3,719 Sq Ft
      • Built 1952
      17 Harrison St, Winchester, MA 01890

      Last Sold Summary

      • 7 Days On Market

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

  • 15 Gershon Way Unit 15, Winchester, MA 01890
    15 Gershon Way Unit 15, Winchester, MA 01890
    15 Gershon Way Unit 15, Winchester, MA 01890
    /35

    $2,325,000

    Sold Jun 18, 2026

    15 Gershon Way Unit 15, Winchester, MA 01890

    • 3 Beds
    • 3.5 Baths
    • 4,087 Sq Ft
    • Built 2020

    Last Sold Summary

    • 3% Below List Price
    • $569/SF
    • 13 Days On Market

    Current Estimated Value $2,171,477

    Last Listing Agent Moira Lown Coldwell Banker Realty - Wellesley

    15 Gershon Way Unit 15, Winchester, MA 01890
    • 27 Cabot St, Winchester, MA 01890
      27 Cabot St, Winchester, MA 01890
      27 Cabot St, Winchester, MA 01890
      /42

      Est $2,852,868

      Not Listed For Sale

      27 Cabot St, Winchester, MA 01890

      • 4 Beds
      • 5 Baths
      • 4,215 Sq Ft
      • Built 1917
      27 Cabot St, Winchester, MA 01890

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent The McLaren D'Agostino Team Compass

  • 9 Norfolk Rd, Winchester, MA 01890
    9 Norfolk Rd, Winchester, MA 01890
    9 Norfolk Rd, Winchester, MA 01890
    /42

    $2,400,000

    Sold Dec 23, 2025

    9 Norfolk Rd, Winchester, MA 01890

    • 6 Beds
    • 3.5 Baths
    • 4,320 Sq Ft
    • Built 1952

    Last Sold Summary

    • $556/SF
    • 6 Days On Market

    Current Estimated Value $2,370,787

    Last Listing Agent Jody Geany Citylight Homes LLC

    9 Norfolk Rd, Winchester, MA 01890
    • 39 Wildwood St, Winchester, MA 01890
      39 Wildwood St, Winchester, MA 01890
      39 Wildwood St, Winchester, MA 01890
      /42

      Est $1,887,789

      Not Listed For Sale

      39 Wildwood St, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 2,131 Sq Ft
      • Built 1930
      39 Wildwood St, Winchester, MA 01890

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Kim Covino Compass

  • 149 Horn Pond Brook Rd, Winchester, MA 01890
    149 Horn Pond Brook Rd, Winchester, MA 01890
    149 Horn Pond Brook Rd, Winchester, MA 01890
    /22

    $1,641,000

    Sold Jan 30, 2026

    149 Horn Pond Brook Rd, Winchester, MA 01890

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

    Last Sold Summary

    • 3% Above List Price
    • $704/SF
    • 0 Days On Market

    Current Estimated Value $1,134,921

    Last Listing Agent Nancy McLaughlin Redfin Corp.

    149 Horn Pond Brook Rd, Winchester, MA 01890
    • 3 Fletcher St, Winchester, MA 01890
      3 Fletcher St, Winchester, MA 01890
      3 Fletcher St, Winchester, MA 01890
      /42

      Est $2,201,922

      Not Listed For Sale

      3 Fletcher St, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 4,031 Sq Ft
      • Built 1886
      3 Fletcher St, Winchester, MA 01890

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Kristine Welch Greater Metropolitan R. E.

  • 4 Wyman Ct Unit 4, Winchester, MA 01890
    4 Wyman Ct Unit 4, Winchester, MA 01890
    4 Wyman Ct Unit 4, Winchester, MA 01890
    /27

    $1,399,000

    Sold Jan 05, 2026

    4 Wyman Ct Unit 4, Winchester, MA 01890

    • 4 Beds
    • 4.5 Baths
    • 2,500 Sq Ft
    • Built 2025

    Last Sold Summary

    • $560/SF
    • 12 Days On Market

    Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    4 Wyman Ct Unit 4, Winchester, MA 01890
    • 19 Yale St, Winchester, MA 01890
      19 Yale St, Winchester, MA 01890
      19 Yale St, Winchester, MA 01890
      /42

      Est $2,461,586

      Not Listed For Sale

      19 Yale St, Winchester, MA 01890

      • 6 Beds
      • 3.5 Baths
      • 4,212 Sq Ft
      • Built 1880
      19 Yale St, Winchester, MA 01890

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

  • 58 Wedgemere Ave, Winchester, MA 01890
    58 Wedgemere Ave, Winchester, MA 01890
    /2

    $3,450,000

    Sold Sep 11, 2025

    58 Wedgemere Ave, Winchester, MA 01890

    • 5 Beds
    • 4.5 Baths
    • 4,800 Sq Ft
    • Built 1932

    Last Sold Summary

    • $719/SF
    • 151 Days On Market

    Current Estimated Value $3,234,535

    Last Listing Agent Mark Donnellan Gibson Sotheby's International Realty

    58 Wedgemere Ave, Winchester, MA 01890
    • 30 Wedgemere Ave, Winchester, MA 01890
      30 Wedgemere Ave, Winchester, MA 01890
      30 Wedgemere Ave, Winchester, MA 01890
      /41

      Est $2,808,102

      Not Listed For Sale

      30 Wedgemere Ave, Winchester, MA 01890

      • 5 Beds
      • 4.5 Baths
      • 4,263 Sq Ft
      • Built 1905
      30 Wedgemere Ave, Winchester, MA 01890

      Last Sold Summary

      • 121 Days On Market

      Last Listing Agent Kim Covino Compass

  • 136 Sylvester Ave, Winchester, MA 01890
    136 Sylvester Ave, Winchester, MA 01890
    136 Sylvester Ave, Winchester, MA 01890
    /36

    $1,156,000

    Sold Feb 25, 2026

    136 Sylvester Ave, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 1,608 Sq Ft
    • Built 1925

    Last Sold Summary

    • 16% Above List Price
    • $719/SF
    • 6 Days On Market

    Current Estimated Value $1,145,396

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    136 Sylvester Ave, Winchester, MA 01890
    • 133 Cambridge St, Winchester, MA 01890
      133 Cambridge St, Winchester, MA 01890
      133 Cambridge St, Winchester, MA 01890
      /33

      Est $1,660,514

      Not Listed For Sale

      133 Cambridge St, Winchester, MA 01890

      • 3 Beds
      • 2.5 Baths
      • 2,938 Sq Ft
      • Built 1946
      133 Cambridge St, Winchester, MA 01890

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Elena Langlois Compass

  • 7 Cliff St, Winchester, MA 01890
    7 Cliff St, Winchester, MA 01890
    7 Cliff St, Winchester, MA 01890
    /3

    $2,800,000

    Sold Jul 07, 2026

    7 Cliff St, Winchester, MA 01890

    • 6 Beds
    • 3.5 Baths
    • 4,573 Sq Ft
    • Built 1890

    Last Sold Summary

    • 12% Above List Price
    • $612/SF
    • 6 Days On Market

    Current Estimated Value $2,523,397

    Last Listing Agent Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

    7 Cliff St, Winchester, MA 01890
    • 24 Calumet Rd, Winchester, MA 01890
      24 Calumet Rd, Winchester, MA 01890
      24 Calumet Rd, Winchester, MA 01890
      /41

      Est $2,505,320

      Not Listed For Sale

      24 Calumet Rd, Winchester, MA 01890

      • 5 Beds
      • 5 Baths
      • 4,182 Sq Ft
      • Built 1927
      24 Calumet Rd, Winchester, MA 01890

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Kim Covino Compass

  • 17 Dennett Rd, Winchester, MA 01890
    17 Dennett Rd, Winchester, MA 01890
    17 Dennett Rd, Winchester, MA 01890
    /41

    $1,500,000

    Sold Oct 09, 2025

    17 Dennett Rd, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,283 Sq Ft
    • Built 1968

    Last Sold Summary

    • 6% Below List Price
    • $657/SF
    • 30 Days On Market

    Current Estimated Value $1,551,507

    Last Listing Agent Kim Covino Compass

    17 Dennett Rd, Winchester, MA 01890
    • 127 Church St, Winchester, MA 01890
      127 Church St, Winchester, MA 01890
      127 Church St, Winchester, MA 01890
      /31

      Not Listed For Sale

      127 Church St, Winchester, MA 01890

      • 7 Beds
      • 5.5 Baths
      • 4,636 Sq Ft
      • Built 1895
      127 Church St, Winchester, MA 01890

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Meredith Caci Mondejar RE/MAX Partners

  • 48 Salisbury St, Winchester, MA 01890
    48 Salisbury St, Winchester, MA 01890
    48 Salisbury St, Winchester, MA 01890
    /39

    $2,600,000

    Sold Nov 21, 2025

    48 Salisbury St, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 4,779 Sq Ft
    • Built 1938

    Last Sold Summary

    • 5% Below List Price
    • $544/SF
    • 44 Days On Market

    Current Estimated Value $2,681,894

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

    48 Salisbury St, Winchester, MA 01890
    • 62 Bacon St, Winchester, MA 01890
      62 Bacon St, Winchester, MA 01890
      62 Bacon St, Winchester, MA 01890
      /42

      Est $1,505,086

      Not Listed For Sale

      62 Bacon St, Winchester, MA 01890

      • 5 Beds
      • 3.5 Baths
      • 2,863 Sq Ft
      • Built 1890
      62 Bacon St, Winchester, MA 01890

      Last Sold Summary

      • 76 Days On Market

      Last Listing Agent Kim Covino Compass

  • 171 Swanton St Unit 60, Winchester, MA 01890
    171 Swanton St Unit 60, Winchester, MA 01890
    171 Swanton St Unit 60, Winchester, MA 01890
    /27

    $738,000

    Sold Sep 26, 2025

    171 Swanton St Unit 60, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 1,824 Sq Ft
    • Built 1985

    Last Sold Summary

    • 14% Above List Price
    • $405/SF
    • 6 Days On Market

    Current Estimated Value $782,434

    Last Listing Agent Michaela Hellman Redfin Corp.

    171 Swanton St Unit 60, Winchester, MA 01890
    • 97 Cambridge St, Winchester, MA 01890
      97 Cambridge St, Winchester, MA 01890
      97 Cambridge St, Winchester, MA 01890
      /35

      Est $1,441,151

      Not Listed For Sale

      97 Cambridge St, Winchester, MA 01890

      • 5 Beds
      • 2.5 Baths
      • 2,430 Sq Ft
      • Built 1889
      97 Cambridge St, Winchester, MA 01890

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Ellen Koswick REMAX Executive Realty

  • 571 Washington St, Winchester, MA 01890
    571 Washington St, Winchester, MA 01890
    571 Washington St, Winchester, MA 01890
    /35

    $900,000

    Sold Jan 05, 2026

    571 Washington St, Winchester, MA 01890

    • 3 Beds
    • 1 Bath
    • 1,425 Sq Ft
    • Built 1920

    Last Sold Summary

    • 6% Below List Price
    • $632/SF
    • 89 Days On Market

    Current Estimated Value $1,002,192

    Last Listing Agent Ryan Wilson Keller Williams Realty

    571 Washington St, Winchester, MA 01890
    • 30 Glen Rd, Winchester, MA 01890
      30 Glen Rd, Winchester, MA 01890
      30 Glen Rd, Winchester, MA 01890
      /42

      Est $2,168,427

      Not Listed For Sale

      30 Glen Rd, Winchester, MA 01890

      • 6 Beds
      • 2.5 Baths
      • 3,892 Sq Ft
      • Built 1910
      30 Glen Rd, Winchester, MA 01890

      Last Sold Summary

      • 35 Days On Market

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

Showing Results 321 - 360, Page 9 of 18

Massachusetts Middlesex County

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group