1,753

West Side Homes

Section Image
  • 17 Wagon Wheel Rd, Winchester, MA 01890
    17 Wagon Wheel Rd, Winchester, MA 01890
    17 Wagon Wheel Rd, Winchester, MA 01890
    /42

    $2,218,500

    Sold Aug 29, 2025

    17 Wagon Wheel Rd, Winchester, MA 01890

    • 5 Beds
    • 5 Baths
    • 3,940 Sq Ft
    • Built 1983

    Last Sold Summary

    • 6% Below List Price
    • $563/SF
    • 74 Days On Market

    Current Estimated Value $2,294,406

    Last Listing Agent Yifei Wang Dreamega International Realty LLC

    17 Wagon Wheel Rd, Winchester, MA 01890
    • 62 Edward Dr, Winchester, MA 01890
      62 Edward Dr, Winchester, MA 01890
      62 Edward Dr, Winchester, MA 01890
      /30

      Est $937,599

      Not Listed For Sale

      62 Edward Dr, Winchester, MA 01890

      • 2 Beds
      • 2.5 Baths
      • 1,857 Sq Ft
      • Built 1985
      62 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

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

  • 7 Wainwright Rd Unit 15, Winchester, MA 01890
    7 Wainwright Rd Unit 15, Winchester, MA 01890
    7 Wainwright Rd Unit 15, Winchester, MA 01890
    /37

    $1,427,000

    Sold Feb 26, 2026

    7 Wainwright Rd Unit 15, Winchester, MA 01890

    • 3 Beds
    • 3.5 Baths
    • 2,996 Sq Ft
    • Built 1988

    Last Sold Summary

    • 6% Above List Price
    • $476/SF
    • 2 Days On Market

    Current Estimated Value $1,411,759

    Last Listing Agent Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

    7 Wainwright Rd Unit 15, Winchester, MA 01890
    • 46 Edward Dr, Winchester, MA 01890
      46 Edward Dr, Winchester, MA 01890
      46 Edward Dr, Winchester, MA 01890
      /27

      Est $1,088,503

      Not Listed For Sale

      46 Edward Dr, Winchester, MA 01890

      • 3 Beds
      • 3.5 Baths
      • 2,859 Sq Ft
      • Built 1985
      46 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Sam Zhu Keller Williams Realty

  • 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
    • 55 Edward Dr, Winchester, MA 01890
      55 Edward Dr, Winchester, MA 01890
      55 Edward Dr, Winchester, MA 01890
      /36

      Est $1,023,075

      Not Listed For Sale

      55 Edward Dr, Winchester, MA 01890

      • 3 Beds
      • 3.5 Baths
      • 2,568 Sq Ft
      • Built 1987
      55 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Anne Spry Barrett Sotheby's International Realty

  • 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
    • 41 Edward Dr, Winchester, MA 01890
      41 Edward Dr, Winchester, MA 01890
      41 Edward Dr, Winchester, MA 01890
      /42

      Est $1,076,384

      Not Listed For Sale

      41 Edward Dr, Winchester, MA 01890

      • 3 Beds
      • 3.5 Baths
      • 2,738 Sq Ft
      • Built 1985
      41 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Beth Sager Group Keller Williams Realty Boston Northwest

  • 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
    • 34 Edward Dr, Winchester, MA 01890
      34 Edward Dr, Winchester, MA 01890
      34 Edward Dr, Winchester, MA 01890
      /38

      Est $1,072,677

      Not Listed For Sale

      34 Edward Dr, Winchester, MA 01890

      • 3 Beds
      • 3.5 Baths
      • 2,754 Sq Ft
      • Built 1985
      34 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • 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
    • 47 Edward Dr, Winchester, MA 01890
      47 Edward Dr, Winchester, MA 01890
      47 Edward Dr, Winchester, MA 01890
      /37

      Est $902,763

      Not Listed For Sale

      47 Edward Dr, Winchester, MA 01890

      • 2 Beds
      • 2 Baths
      • 1,920 Sq Ft
      • Built 1985
      47 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 7 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
    • 25 Henry St, Winchester, MA 01890
      25 Henry St, Winchester, MA 01890
      25 Henry St, Winchester, MA 01890
      /42

      Est $921,607

      Not Listed For Sale

      25 Henry St, Winchester, MA 01890

      • 5 Beds
      • 4.5 Baths
      • 3,890 Sq Ft
      • Built 2021
      25 Henry St, Winchester, MA 01890

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Karima Alami Compass

  • 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
    • 28 Henry St, Winchester, MA 01890
      28 Henry St, Winchester, MA 01890
      28 Henry St, Winchester, MA 01890
      /26

      Est $856,301

      Not Listed For Sale

      28 Henry St, Winchester, MA 01890

      • 2 Beds
      • 1 Bath
      • 1,279 Sq Ft
      • Built 1942
      28 Henry St, Winchester, MA 01890

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Alison Socha Leading Edge Real Estate

  • 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
    • 14 Henry St, Winchester, MA 01890
      14 Henry St, Winchester, MA 01890
      14 Henry St, Winchester, MA 01890
      /42

      Est $1,498,166

      Not Listed For Sale

      14 Henry St, Winchester, MA 01890

      • 6 Beds
      • 3 Baths
      • 3,091 Sq Ft
      • Built 1957
      14 Henry 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

  • 19 Cox Rd, Winchester, MA 01890
    19 Cox Rd, Winchester, MA 01890
    19 Cox Rd, Winchester, MA 01890
    /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 $1,378,104

    Last Listing Agent Kim Covino Compass

    19 Cox Rd, Winchester, MA 01890
    • 14 Locke St, Winchester, MA 01890
      14 Locke St, Winchester, MA 01890
      14 Locke St, Winchester, MA 01890
      /20

      Est $1,069,180

      Not Listed For Sale

      14 Locke St, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 1,432 Sq Ft
      • Built 1910
      14 Locke St, Winchester, MA 01890

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Ruth Gagne Barrett Sotheby's International Realty

  • 54 Johnson Rd, Winchester, MA 01890
    54 Johnson Rd, Winchester, MA 01890
    54 Johnson Rd, Winchester, MA 01890
    /42

    $3,100,000

    Sold May 29, 2026

    54 Johnson Rd, Winchester, MA 01890

    • 5 Beds
    • 7.5 Baths
    • 6,899 Sq Ft
    • Built 2024

    Last Sold Summary

    • 11% Below List Price
    • $449/SF
    • 90 Days On Market

    Current Estimated Value $3,152,269

    Last Listing Agent Kim Covino Compass

    54 Johnson Rd, Winchester, MA 01890
    • 26 Ridge St, Winchester, MA 01890
      26 Ridge St, Winchester, MA 01890
      26 Ridge St, Winchester, MA 01890
      /37

      Est $1,413,403

      Not Listed For Sale

      26 Ridge St, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 2,388 Sq Ft
      • Built 1963
      26 Ridge St, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Dream Team Dreamega International Realty LLC

  • 4 Fieldstone Dr, Winchester, MA 01890
    4 Fieldstone Dr, Winchester, MA 01890
    4 Fieldstone Dr, Winchester, MA 01890
    /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 $2,032,104

    Last Listing Agent Wenli Zheng Fairview Partners International LLC

    4 Fieldstone Dr, Winchester, MA 01890
    • 280 High St, Winchester, MA 01890
      280 High St, Winchester, MA 01890
      280 High St, Winchester, MA 01890
      /40

      Est $2,363,468

      Not Listed For Sale

      280 High St, Winchester, MA 01890

      • 6 Beds
      • 5 Baths
      • 6,259 Sq Ft
      • Built 1976
      280 High St, Winchester, MA 01890

      Last Sold Summary

      • 136 Days On Market

      Last Listing Agent Anthony Marino The Marino Group Collection

  • 26 Berkshire Dr, Winchester, MA 01890
    26 Berkshire Dr, Winchester, MA 01890
    26 Berkshire Dr, Winchester, MA 01890
    /41

    $1,400,000

    Sold Mar 06, 2026

    26 Berkshire Dr, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,316 Sq Ft
    • Built 1970

    Last Sold Summary

    • 5% Below List Price
    • $604/SF
    • 77 Days On Market

    Current Estimated Value $1,431,866

    Last Listing Agent Daniel Beirne OpenDoor Brokerage LLC

    26 Berkshire Dr, Winchester, MA 01890
    • 34 Coolidge Rd, Winchester, MA 01890
      34 Coolidge Rd, Winchester, MA 01890
      34 Coolidge Rd, Winchester, MA 01890
      /33

      Est $1,714,714

      Not Listed For Sale

      34 Coolidge Rd, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 3,338 Sq Ft
      • Built 1980
      34 Coolidge Rd, Winchester, MA 01890

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Pauline Marino Coldwell Banker Realty - Lexington

  • 12 Cox Rd, Winchester, MA 01890
    12 Cox Rd, Winchester, MA 01890
    12 Cox Rd, Winchester, MA 01890
    /41

    $1,699,000

    Sold Aug 06, 2026

    12 Cox Rd, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,818 Sq Ft
    • Built 1955

    Last Sold Summary

    • 6% Below List Price
    • $603/SF
    • 25 Days On Market

    Current Estimated Value $1,681,763

    Last Listing Agent Darryl Brian RE/MAX Bentley's

    12 Cox Rd, Winchester, MA 01890
    • 31 Coolidge Rd, Winchester, MA 01890
      31 Coolidge Rd, Winchester, MA 01890
      31 Coolidge Rd, Winchester, MA 01890
      /41

      Est $1,932,103

      Not Listed For Sale

      31 Coolidge Rd, Winchester, MA 01890

      • 4 Beds
      • 4 Baths
      • 4,650 Sq Ft
      • Built 1980
      31 Coolidge Rd, Winchester, MA 01890

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

  • 63 Dunster Ln, Winchester, MA 01890
    63 Dunster Ln, Winchester, MA 01890
    63 Dunster Ln, Winchester, MA 01890
    /9

    $825,000

    Sold Jul 31, 2026

    63 Dunster Ln, Winchester, MA 01890

    • 2 Beds
    • 1 Bath
    • 1,208 Sq Ft
    • Built 1910

    Last Sold Summary

    • 2% Above List Price
    • $683/SF
    • 9 Days On Market

    Current Estimated Value $817,464

    Last Listing Agent john ferolito Keller Williams Realty

    63 Dunster Ln, Winchester, MA 01890
    • 23 Olde Village Dr, Winchester, MA 01890
      23 Olde Village Dr, Winchester, MA 01890
      23 Olde Village Dr, Winchester, MA 01890
      /42

      Est $2,090,287

      Not Listed For Sale

      23 Olde Village Dr, Winchester, MA 01890

      • 3 Beds
      • 3.5 Baths
      • 4,997 Sq Ft
      • Built 1975
      23 Olde Village Dr, Winchester, MA 01890

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • 139 High St, Winchester, MA 01890
    139 High St, Winchester, MA 01890
    139 High St, Winchester, MA 01890
    /24

    $945,000

    Sold Feb 12, 2026

    139 High St, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 1,302 Sq Ft
    • Built 1949

    Last Sold Summary

    • 5% Below List Price
    • $726/SF
    • 61 Days On Market

    Current Estimated Value $1,043,516

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

    139 High St, Winchester, MA 01890
    • 31 Girard Rd, Winchester, MA 01890
      31 Girard Rd, Winchester, MA 01890
      31 Girard Rd, Winchester, MA 01890
      /38

      Est $1,730,966

      Not Listed For Sale

      31 Girard Rd, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 3,158 Sq Ft
      • Built 1975
      31 Girard Rd, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Philip Vita Compass

  • 8 Buckman Dr, Winchester, MA 01890
    8 Buckman Dr, Winchester, MA 01890
    8 Buckman Dr, Winchester, MA 01890
    /41

    $2,380,000

    Sold Feb 25, 2026

    8 Buckman Dr, Winchester, MA 01890

    • 5 Beds
    • 5.5 Baths
    • 4,773 Sq Ft
    • Built 1970

    Last Sold Summary

    • 4% Above List Price
    • $499/SF
    • 4 Days On Market

    Current Estimated Value $2,357,812

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    8 Buckman Dr, Winchester, MA 01890
    • 99 Ridge St, Winchester, MA 01890
      99 Ridge St, Winchester, MA 01890
      99 Ridge St, Winchester, MA 01890
      /40

      Est $2,174,236

      Not Listed For Sale

      99 Ridge St, Winchester, MA 01890

      • 5 Beds
      • 3.5 Baths
      • 4,567 Sq Ft
      • Built 2004
      99 Ridge St, Winchester, MA 01890

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Doug Hills Compass

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

    $1,775,000

    Sold Aug 15, 2025

    19 Pilgrim Dr, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 3,150 Sq Ft
    • Built 1961

    Last Sold Summary

    • $563/SF
    • 6 Days On Market

    Current Estimated Value $1,846,914

    Last Listing Agent Gorfinkle Group eXp Realty LLC - Corporate Office

    19 Pilgrim Dr, Winchester, MA 01890
    • 119 Ridge St, Winchester, MA 01890
      119 Ridge St, Winchester, MA 01890
      119 Ridge St, Winchester, MA 01890
      /42

      Est $1,248,155

      Not Listed For Sale

      119 Ridge St, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 2,542 Sq Ft
      • Built 1956
      119 Ridge St, Winchester, MA 01890

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Charles Jolin Keller Williams Realty

  • 15 Westland Ave, Winchester, MA 01890
    15 Westland Ave, Winchester, MA 01890
    15 Westland Ave, Winchester, MA 01890
    /42

    $1,750,000

    Sold Oct 31, 2025

    15 Westland Ave, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,397 Sq Ft
    • Built 1937

    Last Sold Summary

    • $730/SF
    • 1 Day On Market

    Current Estimated Value $1,694,830

    Last Listing Agent Erica Carson Coldwell Banker Realty - Lexington

    15 Westland Ave, Winchester, MA 01890
    • 50 Johnson Rd, Winchester, MA 01890
      50 Johnson Rd, Winchester, MA 01890
      50 Johnson Rd, Winchester, MA 01890
      /42

      Est $1,733,152

      Not Listed For Sale

      50 Johnson Rd, Winchester, MA 01890

      • 3 Beds
      • 4 Baths
      • 2,646 Sq Ft
      • Built 1957
      50 Johnson Rd, Winchester, MA 01890

      Last Sold Summary

      • 18 Days On Market

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

  • 189 High St, Winchester, MA 01890
    189 High St, Winchester, MA 01890
    189 High St, Winchester, MA 01890
    /41

    $1,191,000

    Sold Jan 13, 2026

    189 High St, Winchester, MA 01890

    • 4 Beds
    • 3 Baths
    • 2,126 Sq Ft
    • Built 1951

    Last Sold Summary

    • 4% Above List Price
    • $560/SF
    • 8 Days On Market

    Current Estimated Value $1,257,771

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

    189 High St, Winchester, MA 01890
    • 25 Lockeland Rd, Winchester, MA 01890
      25 Lockeland Rd, Winchester, MA 01890
      25 Lockeland Rd, Winchester, MA 01890
      /40

      Est $1,427,756

      Not Listed For Sale

      25 Lockeland Rd, Winchester, MA 01890

      • 3 Beds
      • 3 Baths
      • 2,456 Sq Ft
      • Built 1954
      25 Lockeland Rd, Winchester, MA 01890

      Last Sold Summary

      • 12 Days On Market

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

Showing Results 81 - 120, Page 3 of 18

Massachusetts Middlesex County Winchester

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