56

Recently Sold West Side Homes

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  • /42

    $1,055,000

    Sold May 15, 2026

    15 Edward Dr Unit 15, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,082 Sq Ft
    • Built 1985

    Last Sold Summary

    • 10% Above List Price
    • $507/SF
    • 5 Days On Market

    Last Listing Agent Alina Wang Coldwell Banker Realty - Lexington

    15 Edward Dr Unit 15, Winchester, MA 01890
  • /31

    $1,240,000

    Sold Apr 27, 2026

    12 Thornberry Rd, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 2,087 Sq Ft
    • Built 1957

    Last Sold Summary

    • 3% Above List Price
    • $594/SF
    • 6 Days On Market

    Current Estimated Value $1,238,250

    Last Listing Agent Kim Covino Compass

    12 Thornberry Rd, Winchester, MA 01890
  • /42

    $1,055,000

    Sold Feb 26, 2026

    7 Trinity Rd, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,130 Sq Ft
    • Built 1963

    Last Sold Summary

    • 11% Below List Price
    • $495/SF
    • 24 Days On Market

    Current Estimated Value $1,194,782

    Last Listing Agent Gayle Winters Compass

    7 Trinity Rd, Winchester, MA 01890
  • /42

    $1,580,000

    Sold Feb 26, 2026

    10 Trinity Rd, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,112 Sq Ft
    • Built 1963

    Last Sold Summary

    • 11% Above List Price
    • $748/SF
    • 5 Days On Market

    Current Estimated Value $1,582,082

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    10 Trinity Rd, Winchester, MA 01890
  • /41

    $1,360,000

    Sold Jul 29, 2026

    15 Thornberry Rd, Winchester, MA 01890

    • 4 Beds
    • 3 Baths
    • 4,062 Sq Ft
    • Built 1957

    Last Sold Summary

    • 1% Above List Price
    • $335/SF
    • 7 Days On Market

    Current Estimated Value $1,365,421

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

    15 Thornberry Rd, Winchester, MA 01890
  • /39

    $2,050,000

    Sold Oct 15, 2025

    64 Westland Ave, Winchester, MA 01890

    • 4 Beds
    • 5 Baths
    • 3,716 Sq Ft
    • Built 1931

    Last Sold Summary

    • $552/SF
    • 2 Days On Market

    Current Estimated Value $2,065,323

    Last Listing Agent The Murphy Group Lexington William Raveis R.E. & Home Services

    64 Westland Ave, Winchester, MA 01890
  • /38

    $1,525,000

    Sold Sep 12, 2025

    5 Thornton Rd, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 2,755 Sq Ft
    • Built 1929

    Last Sold Summary

    • 12% Below List Price
    • $554/SF
    • 30 Days On Market

    Current Estimated Value $1,842,055

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

    5 Thornton Rd, Winchester, MA 01890
  • /40

    $3,150,000

    Sold May 28, 2026

    257 High St, Winchester, MA 01890

    • 5 Beds
    • 7 Baths
    • 7,101 Sq Ft
    • Built 1994

    Last Sold Summary

    • 3% Below List Price
    • $444/SF
    • 2 Days On Market

    Current Estimated Value $3,184,671

    Last Listing Agent Kim Covino Compass

    257 High St, Winchester, MA 01890
  • /33

    $1,936,000

    Sold Jun 23, 2026

    2 Gershon Way Unit 2, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,306 Sq Ft
    • Built 2019

    Last Sold Summary

    • 2% Above List Price
    • $840/SF
    • 7 Days On Market

    Current Estimated Value $1,891,624

    Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    2 Gershon Way Unit 2, Winchester, MA 01890
  • /42

    $1,700,000

    Sold Jun 29, 2026

    29 Pilgrim Dr, Winchester, MA 01890

    • 5 Beds
    • 3 Baths
    • 3,271 Sq Ft
    • Built 1963

    Last Sold Summary

    • 3% Below List Price
    • $520/SF
    • 20 Days On Market

    Current Estimated Value $1,735,379

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    29 Pilgrim Dr, Winchester, MA 01890
  • /24

    $2,155,000

    Sold Oct 21, 2025

    7 Wainwright Rd Unit 13, Winchester, MA 01890

    • 3 Beds
    • 4.5 Baths
    • 3,186 Sq Ft
    • Built 1988

    Last Sold Summary

    • $676/SF
    • 1 Day On Market

    Current Estimated Value $1,894,572

    Last Listing Agent Isabella Bruno William Raveis R.E. & Home Services

    7 Wainwright Rd Unit 13, Winchester, MA 01890
  • /42

    $1,700,000

    Sold May 01, 2026

    114 Johnson Rd, Winchester, MA 01890

    • 3 Beds
    • 3 Baths
    • 3,182 Sq Ft
    • Built 1880

    Last Sold Summary

    • 5% Below List Price
    • $534/SF
    • 22 Days On Market

    Current Estimated Value $1,696,035

    Last Listing Agent Rosemary Kelleher LAER Realty Partners

    114 Johnson Rd, Winchester, MA 01890
  • /42

    $1,550,000

    Sold Oct 31, 2025

    205 Ridge St, Winchester, MA 01890

    • 5 Beds
    • 3 Baths
    • 2,995 Sq Ft
    • Built 1960

    Last Sold Summary

    • $518/SF
    • 5 Days On Market

    Current Estimated Value $1,635,363

    Last Listing Agent Debby Valdes eXp Realty LLC

    205 Ridge St, Winchester, MA 01890
  • /23

    $1,440,150

    Sold Jun 01, 2026

    65 High St, Winchester, MA 01890

    • 6 Beds
    • 3 Baths
    • 2,658 Sq Ft
    • Built 1949

    Last Sold Summary

    • 3% Above List Price
    • $542/SF
    • 5 Days On Market

    Current Estimated Value $1,448,958

    Last Listing Agent Anna Jung K Stadium Realty INC

    65 High St, Winchester, MA 01890
  • /34

    $2,100,000

    Sold Mar 19, 2026

    10 Hawthorne Rd, Winchester, MA 01890

    • 5 Beds
    • 6 Baths
    • 3,191 Sq Ft
    • Built 1961

    Last Sold Summary

    • 5% Above List Price
    • $658/SF
    • 7 Days On Market

    Current Estimated Value $2,051,683

    Last Listing Agent Susan Kadilak Fiv Realty Co.

    10 Hawthorne Rd, Winchester, MA 01890
  • /42

    $1,090,000

    Sold Feb 06, 2026

    16 Ridge St, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 1,844 Sq Ft
    • Built 1965

    Last Sold Summary

    • 9% Below List Price
    • $591/SF
    • 82 Days On Market

    Current Estimated Value $1,162,361

    Last Listing Agent Kim Covino Compass

    16 Ridge St, Winchester, MA 01890
  • /32

    $1,475,000

    Sold Apr 29, 2026

    28 Emerson Rd, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 2,344 Sq Ft
    • Built 1952

    Last Sold Summary

    • 9% Above List Price
    • $629/SF
    • 4 Days On Market

    Current Estimated Value $1,466,943

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    28 Emerson Rd, Winchester, MA 01890
  • /41

    $1,810,000

    Sold May 18, 2026

    12 Wincrest Dr, Winchester, MA 01890

    • 6 Beds
    • 4.5 Baths
    • 3,833 Sq Ft
    • Built 1968

    Last Sold Summary

    • 3% Above List Price
    • $472/SF
    • 5 Days On Market

    Current Estimated Value $1,785,611

    Last Listing Agent Kim Covino Compass

    12 Wincrest Dr, Winchester, MA 01890
  • /28

    $1,713,000

    Sold Sep 26, 2025

    44 Amberwood Dr, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 3,002 Sq Ft
    • Built 1983

    Last Sold Summary

    • 11% Below List Price
    • $571/SF
    • 53 Days On Market

    Current Estimated Value $1,828,282

    Last Listing Agent Hudson Santana Keller Williams Realty Boston Northwest

    44 Amberwood Dr, Winchester, MA 01890
  • /24

    $1,165,000

    Sold Oct 14, 2025

    59 Johnson Rd, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,458 Sq Ft
    • Built 1958

    Last Sold Summary

    • 10% Below List Price
    • $474/SF
    • 43 Days On Market

    Current Estimated Value $1,269,130

    Last Listing Agent Angela Zhang Greatland Real Estate LLC

    59 Johnson Rd, Winchester, MA 01890
  • /41

    $2,150,000

    Sold Nov 05, 2025

    7 Wainwright Rd Unit 72, Winchester, MA 01890

    • 4 Beds
    • 4.5 Baths
    • 3,512 Sq Ft
    • Built 1989

    Last Sold Summary

    • 10% Above List Price
    • $612/SF
    • 7 Days On Market

    Current Estimated Value $2,121,373

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

    7 Wainwright Rd Unit 72, Winchester, MA 01890
  • /33

    $1,502,500

    Sold Jan 10, 2026

    7 Wainwright Rd Unit 118, Winchester, MA 01890

    • 3 Beds
    • 3.5 Baths
    • 3,807 Sq Ft
    • Built 1995

    Last Sold Summary

    • $395/SF
    • 5 Days On Market

    Current Estimated Value $1,567,046

    Last Listing Agent Giordana Fiorvanti-Smith Berkshire Hathaway HomeServices Commonwealth Real Estate

    7 Wainwright Rd Unit 118, Winchester, MA 01890
  • /35

    $1,310,000

    Sold Dec 24, 2025

    7 Thornberry Rd, Winchester, MA 01890

    • 5 Beds
    • 2 Baths
    • 3,033 Sq Ft
    • Built 1957

    Last Sold Summary

    • 5% Below List Price
    • $432/SF
    • 73 Days On Market

    Current Estimated Value $1,377,062

    Last Listing Agent Kim Covino Compass

    7 Thornberry Rd, Winchester, MA 01890
  • /40

    $1,515,000

    Sold May 22, 2026

    7 Wainwright Rd Unit 107, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,907 Sq Ft
    • Built 1995

    Last Sold Summary

    • 12% Above List Price
    • $521/SF
    • 8 Days On Market

    Current Estimated Value $1,430,814

    Last Listing Agent Kim Covino Compass

    7 Wainwright Rd Unit 107, 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 $1,773,092

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

    61 Westland Ave, 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 $2,185,175

    Last Listing Agent Moira Lown Coldwell Banker Realty - Wellesley

    15 Gershon Way Unit 15, Winchester, MA 01890
  • /42

    $1,987,000

    Sold Nov 18, 2025

    6 Samoset Rd, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 4,731 Sq Ft
    • Built 1992

    Last Sold Summary

    • 1% Below List Price
    • $420/SF
    • 16 Days On Market

    Current Estimated Value $2,131,700

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    6 Samoset Rd, Winchester, MA 01890
  • /19

    $1,820,000

    Sold Aug 19, 2025

    109 Thornberry Rd, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 3,784 Sq Ft
    • Built 1974

    Last Sold Summary

    • 1% Above List Price
    • $481/SF
    • 5 Days On Market

    Current Estimated Value $1,934,115

    Last Listing Agent Andrew Martini Compass

    109 Thornberry 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 $2,275,140

    Last Listing Agent Yifei Wang Dreamega International Realty LLC

    17 Wagon Wheel Rd, 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 $1,424,566

    Last Listing Agent Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

    7 Wainwright Rd Unit 15, 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 $1,743,559

    Last Listing Agent Stephen DeConto Cameron Real Estate Group

    10 Blossom Hill 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 $1,633,795

    Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    105 Thornberry Rd, 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 $1,740,809

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

    9 Pilgrim Dr, 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 $1,841,893

    Last Listing Agent The McLaren D'Agostino Team Compass

    4 Aricia Ln, 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
  • /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 $1,940,282

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    5 Squire Rd, 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
  • /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 $1,384,063

    Last Listing Agent Kim Covino Compass

    19 Cox 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 $3,315,670

    Last Listing Agent Kim Covino Compass

    54 Johnson Rd, 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 $2,042,070

    Last Listing Agent Wenli Zheng Fairview Partners International LLC

    4 Fieldstone Dr, Winchester, MA 01890

Showing Results 1 - 40, Page 1 of 2

Frequently Asked Questions

What is the average time to sell a house in West Side, MA?
The houses for sale in West Side, MA spend an average of 20 days on the market.
What is the number of active homes for sale in West Side, MA?
There are 12 active homes for sale in West Side, MA.

Home Price Trends

Median Sale Price
$1,700,000
Median Single Family Sale Price
$1,706,500
Median Townhouse Sale Price
$2,130,500
Median 2 Bedroom Sale Price
$825,000
Average Price Per Sq Ft
$538
Number of Homes for Sale
12
Last 12 months Home Sales
57
Months of Supply
2.50
Median List Price
$1,750,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
7%
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