1,776

West Side Homes

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  • /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 $1,899,613

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    5 Squire Rd, Winchester, MA 01890
    • /27

      Est $1,059,932 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

      • 15% Above List Price
      • $324/SF
      • 8 Days On Market
      • Last Sold Price $925,000
      • Nov 20, 2023

      Last Listing Agent Sam Zhu Keller Williams Realty

  • /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
    • /36

      Est $975,813 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

      • $380/SF
      • 6 Days On Market
      • Last Sold Price $975,000
      • Sep 16, 2024

      Last Listing Agent Anne Spry Barrett Sotheby's International Realty

  • /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
    • /42

      Est $1,056,407 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

      • 19% Above List Price
      • $323/SF
      • 17 Days On Market
      • Last Sold Price $885,000
      • Aug 01, 2023

      Last Listing Agent Beth Sager Group Keller Williams Realty Boston Northwest

  • /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
    • /38

      Est $1,050,154 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

      • 11% Above List Price
      • $345/SF
      • 6 Days On Market
      • Last Sold Price $950,000
      • Apr 23, 2024

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • /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 $1,465,260

    Last Listing Agent DANIEL BEIRNE OpenDoor Brokerage LLC

    26 Berkshire Dr, Winchester, MA 01890
    • /37

      Est $910,267 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

      • 25% Above List Price
      • $379/SF
      • 7 Days On Market
      • Last Sold Price $727,500
      • Jan 05, 2024

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • /33

    $1,650,000 Sold Jun 06, 2025

    34 Coolidge Rd, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 3,338 Sq Ft
    • Built 1980

    Last Sold Summary

    • 3% Above List Price
    • $494/SF
    • 7 Days On Market

    Current Estimated Value $1,717,734

    Last Listing Agent Pauline Marino Coldwell Banker Realty - Lexington

    34 Coolidge Rd, Winchester, MA 01890
    • /31

      Est $1,818,912 Not Listed For Sale

      56 Ridge St, Winchester, MA 01890

      • 4 Beds
      • 4 Baths
      • 4,028 Sq Ft
      • Built 1973
      56 Ridge St, Winchester, MA 01890

      Last Sold Summary

      • 14% Above List Price
      • $397/SF
      • 5 Days On Market
      • Last Sold Price $1,600,000
      • May 31, 2023

      Last Listing Agent Philip Vita Compass

  • /39

    $1,425,000 Sold Jun 25, 2025

    9 Thornberry Rd, Winchester, MA 01890

    • 4 Beds
    • 3 Baths
    • 2,496 Sq Ft
    • Built 1957

    Last Sold Summary

    • 8% Above List Price
    • $571/SF
    • 6 Days On Market

    Current Estimated Value $1,406,088

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

    9 Thornberry Rd, Winchester, MA 01890
    • /23

      Est $975,280 Not Listed For Sale

      12 James St, Winchester, MA 01890

      • 3 Beds
      • 1.5 Baths
      • 1,548 Sq Ft
      • Built 1950
      12 James St, Winchester, MA 01890

      Last Sold Summary

      • 15% Above List Price
      • $548/SF
      • 25 Days On Market
      • Last Sold Price $849,000
      • Jul 25, 2023

      Last Listing Agent Gigi Nguyen Harmony Hill Realty LLC

  • /26

    $1,140,000 Sold Jun 03, 2025

    7 Indian Hill Rd, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 1,646 Sq Ft
    • Built 1955

    Last Sold Summary

    • 1% Below List Price
    • $693/SF
    • 8 Days On Market

    Current Estimated Value $1,266,590

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

    7 Indian Hill Rd, Winchester, MA 01890
    • /42

      Est $995,505 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

      • 34% Below List Price
      • $388/SF
      • 3 Days On Market
      • Last Sold Price $1,510,000
      • Jan 24, 2024

      Last Listing Agent Karima Alami Compass

  • /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 $966,800

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

    139 High St, Winchester, MA 01890
    • /26

      Est $857,084 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

      • 20% Above List Price
      • $559/SF
      • 5 Days On Market
      • Last Sold Price $715,000
      • Oct 25, 2023

      Last Listing Agent Alison Socha Leading Edge Real Estate

  • /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 $2,314,729

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    8 Buckman Dr, Winchester, MA 01890
    • /42

      Est $1,420,894 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

      • 6% Below List Price
      • $491/SF
      • 7 Days On Market
      • Last Sold Price $1,517,500
      • Jan 09, 2025

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

  • /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 $1,809,077

    Last Listing Agent Gorfinkle Group eXp Realty

    19 Pilgrim Dr, Winchester, MA 01890
    • /20

      Est $1,089,149 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

      • 13% Above List Price
      • $670/SF
      • 35 Days On Market
      • Last Sold Price $960,000
      • Aug 24, 2023

      Last Listing Agent Ruth Gagne Barrett Sotheby's International Realty

  • /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 $1,679,046

    Last Listing Agent Erica Carson Coldwell Banker Realty - Lexington

    15 Westland Ave, Winchester, MA 01890
    • /17

      Est $1,947,875 Not Listed For Sale

      21 Dunster Ln, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 3,578 Sq Ft
      • Built 1950
      21 Dunster Ln, Winchester, MA 01890

      Last Sold Summary

      • 3% Below List Price
      • $559/SF
      • 9 Days On Market
      • Last Sold Price $2,000,000
      • Jul 25, 2023

      Last Listing Agent Mark Donnellan Gibson Sotheby's International Realty

  • /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 $1,205,544

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

    189 High St, Winchester, MA 01890
    • /38

      Est $1,234,471 Not Listed For Sale

      18 Ridge St, Winchester, MA 01890

      • 5 Beds
      • 1.5 Baths
      • 2,383 Sq Ft
      • Built 1840
      18 Ridge St, Winchester, MA 01890

      Last Sold Summary

      • 18% Above List Price
      • $441/SF
      • 15 Days On Market
      • Last Sold Price $1,050,000
      • Apr 04, 2024

      Last Listing Agent Gayle Winters Compass

  • /42

    $1,999,000 Sold Dec 12, 2025

    5 Azalea Rd, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 6,232 Sq Ft
    • Built 1980

    Last Sold Summary

    • 6% Below List Price
    • $321/SF
    • 59 Days On Market

    Current Estimated Value $2,024,064

    Last Listing Agent Anthony Marino The Marino Group Collection

    5 Azalea Rd, Winchester, MA 01890
    • /40

      Est $2,368,607 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

      • 20% Above List Price
      • $316/SF
      • 136 Days On Market
      • Last Sold Price $1,980,000
      • Sep 30, 2024

      Last Listing Agent Anthony Marino The Marino Group Collection

  • /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 $1,640,759

    Last Listing Agent Darryl Brian RE/MAX Bentley's

    10 Olde Lyme Rd, Winchester, MA 01890
    • /41

      Est $2,025,981 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

      • 1% Above List Price
      • $430/SF
      • 11 Days On Market
      • Last Sold Price $2,000,000
      • Apr 15, 2025

      Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

  • /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 $1,000,199

    Last Listing Agent William Cordts Coldwell Banker Realty - Waltham

    41 Squire Rd, Winchester, MA 01890
    • /42

      Est $2,067,887 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

      • 2% Above List Price
      • $405/SF
      • 8 Days On Market
      • Last Sold Price $2,025,000
      • Feb 21, 2025

      Last Listing Agent Ngoc Anh Goldstein Leading Edge Real Estate

  • /41

    $1,500,000 Sold Jun 30, 2025

    7 Wainwright Rd Unit 117, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 4,214 Sq Ft
    • Built 1995

    Last Sold Summary

    • $356/SF
    • 4 Days On Market

    Current Estimated Value $1,677,482

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    7 Wainwright Rd Unit 117, Winchester, MA 01890
    • /38

      Est $1,648,420 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

      • $522/SF
      • 6 Days On Market
      • Last Sold Price $1,650,000
      • Dec 11, 2024

      Last Listing Agent Philip Vita Compass

  • /37

    $1,450,000 Sold May 30, 2025

    7 Wainwright Rd Unit 8, Winchester, MA 01890

    • 3 Beds
    • 3.5 Baths
    • 3,763 Sq Ft
    • Built 1988

    Last Sold Summary

    • 9% Below List Price
    • $385/SF
    • 34 Days On Market

    Current Estimated Value $1,521,039

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

    7 Wainwright Rd Unit 8, Winchester, MA 01890
    • /40

      Est $2,045,016 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

      • 7% Above List Price
      • $418/SF
      • 4 Days On Market
      • Last Sold Price $1,910,000
      • Jun 26, 2024

      Last Listing Agent Doug Hills Compass

  • /42

    $2,500,000 Sold Aug 27, 2025

    12 Olde Lyme Rd, Winchester, MA 01890

    • 5 Beds
    • 4.5 Baths
    • 4,215 Sq Ft
    • Built 1955

    Last Sold Summary

    • 4% Above List Price
    • $593/SF
    • 4 Days On Market

    Current Estimated Value $2,423,020

    Last Listing Agent Mary Beth McGillicuddy Engel & Völkers , South Shore

    12 Olde Lyme Rd, Winchester, MA 01890
    • /42

      Est $1,245,518 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

      • 22% Above List Price
      • $403/SF
      • 31 Days On Market
      • Last Sold Price $1,025,000
      • Jul 31, 2024

      Last Listing Agent Charles Jolin Keller Williams Realty

  • /40

    $1,510,000 Sold Jun 09, 2025

    7 Hutchinson Rd, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 3,406 Sq Ft
    • Built 1959

    Last Sold Summary

    • 10% Above List Price
    • $443/SF
    • 5 Days On Market

    Current Estimated Value $1,560,916

    Last Listing Agent Kim Covino Compass

    7 Hutchinson Rd, Winchester, MA 01890
    • /41

      Est $3,841,638 Not Listed For Sale

      11 Viking Rd, Winchester, MA 01890

      • 5 Beds
      • 4.5 Baths
      • 4,322 Sq Ft
      • Built 1980
      11 Viking Rd, Winchester, MA 01890

      Last Sold Summary

      • 159% Above List Price
      • $344/SF
      • 9 Days On Market
      • Last Sold Price $1,485,000
      • Sep 27, 2023

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

Showing Results 81 - 120, Page 3 of 18

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