296

Recently Sold Winchester, MA Homes

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  • /30

    $729,000

    Sold Aug 12, 2026

    171 Swanton St Unit 7, Winchester, MA 01890

    • 2 Beds
    • 2.5 Baths
    • 1,431 Sq Ft
    • Built 1984

    Last Sold Summary

    • $509/SF
    • 19 Days On Market

    Current Estimated Value $738,713

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

    171 Swanton St Unit 7, Winchester, MA 01890
  • /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
  • /35

    $1,379,000

    Sold Jan 05, 2026

    6 Wyman Ct Unit 6, Winchester, MA 01890

    • 3 Beds
    • 4.5 Baths
    • 2,722 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Below List Price
    • $507/SF
    • 15 Days On Market

    Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    6 Wyman Ct Unit 6, Winchester, MA 01890
  • /42

    $1,255,000

    Sold Jan 07, 2026

    104 Church St, Winchester, MA 01890

    • 4 Beds
    • 1.5 Baths
    • 2,696 Sq Ft
    • Built 1897

    Last Sold Summary

    • 10% Below List Price
    • $466/SF
    • 46 Days On Market

    Current Estimated Value $1,397,049

    Last Listing Agent Kim Covino Compass

    104 Church St, Winchester, MA 01890
  • /17

    $330,000

    Sold Jul 28, 2026

    200 Swanton St Unit 228, Winchester, MA 01890

    • 1 Bed
    • 1 Bath
    • 606 Sq Ft
    • Built 1966

    Last Sold Summary

    • 17% Below List Price
    • $545/SF
    • 199 Days On Market

    Current Estimated Value $370,419

    Last Listing Agent Joan Powell REMAX Andrew Realty Services

    200 Swanton St Unit 228, Winchester, MA 01890
  • 2 Edgewater Place, Winchester, MA 01890

    $2,575,000

    Sold Jun 16, 2026

    2 Edgewater Place, Winchester, MA 01890

    • 4 Beds
    • 4.5 Baths
    • 3,945 Sq Ft
    • Built 1959

    Last Sold Summary

    • 8% Below List Price
    • $653/SF
    • 34 Days On Market

    Current Estimated Value $2,624,187

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    2 Edgewater Place, Winchester, MA 01890
  • /39

    $1,560,000

    Sold Apr 30, 2026

    17 Cranston Rd, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,578 Sq Ft
    • Built 1950

    Last Sold Summary

    • $605/SF
    • 5 Days On Market

    Current Estimated Value $1,558,066

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    17 Cranston 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 $1,191,098

    Last Listing Agent Gayle Winters Compass

    7 Trinity Rd, Winchester, MA 01890
  • /42

    $1,750,000

    Sold Jul 09, 2026

    24 Hinds Rd, Winchester, MA 01890

    • 4 Beds
    • 3 Baths
    • 2,814 Sq Ft
    • Built 1955

    Last Sold Summary

    • 3% Below List Price
    • $622/SF
    • 7 Days On Market

    Current Estimated Value $1,747,039

    Last Listing Agent Kim Covino Compass

    24 Hinds Rd, Winchester, MA 01890
  • /39

    $2,150,000

    Sold Jul 13, 2026

    22 Hollywood Rd, Winchester, MA 01890

    • 5 Beds
    • 4 Baths
    • 3,136 Sq Ft
    • Built 1962

    Last Sold Summary

    • 8% Above List Price
    • $686/SF
    • 8 Days On Market

    Current Estimated Value $1,971,943

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    22 Hollywood Rd, Winchester, MA 01890
  • /3

    $1,930,000

    Sold Jan 09, 2026

    8 Felsdale Close, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 3,658 Sq Ft
    • Built 1935

    Last Sold Summary

    • 7% Below List Price
    • $528/SF
    • 35 Days On Market

    Current Estimated Value $1,958,095

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    8 Felsdale Close, Winchester, MA 01890
  • /41

    $3,230,000

    Sold Aug 21, 2026

    2 Everett Ave, Winchester, MA 01890

    • 7 Beds
    • 6 Baths
    • 7,043 Sq Ft
    • Built 1916

    Last Sold Summary

    • 14% Below List Price
    • $459/SF
    • 99 Days On Market

    Current Estimated Value $3,484,883

    Last Listing Agent Joan Francis Sullivan Better Homes and Gardens Real Estate - The Shanahan Group

    2 Everett Ave, 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 $1,543,175

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    10 Trinity Rd, Winchester, MA 01890
  • /40

    $1,715,000

    Sold Sep 03, 2026

    94 Johnson Rd, Winchester, MA 01890

    • 4 Beds
    • 3 Baths
    • 3,366 Sq Ft
    • Built 1971

    Last Sold Summary

    • 5% Below List Price
    • $510/SF
    • 34 Days On Market

    Current Estimated Value $1,782,114

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

    94 Johnson 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
  • /28

    $1,200,000

    Sold May 29, 2026

    31 Mystic Ave Unit 33, Winchester, MA 01890

    • 4 Beds
    • 2 Baths
    • 2,129 Sq Ft
    • Built 1890

    Last Sold Summary

    • $564/SF
    • 27 Days On Market

    Last Listing Agent Kim Covino Compass

    31 Mystic Ave Unit 33, Winchester, MA 01890
  • /18

    $452,500

    Sold Mar 30, 2026

    22 Oak St, Winchester, MA 01890

    • 3 Beds
    • 1 Bath
    • 1,573 Sq Ft
    • Built 1910

    Last Sold Summary

    • $288/SF
    • 2 Days On Market

    Current Estimated Value $485,816

    Last Listing Agent Rameel Rana Advise Realty

    22 Oak St, Winchester, MA 01890
  • /35

    $1,325,000

    Sold Aug 14, 2026

    3 Chesterford Terrace, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 2,006 Sq Ft
    • Built 1933

    Last Sold Summary

    • 2% Above List Price
    • $661/SF
    • 10 Days On Market

    Current Estimated Value $1,410,363

    Last Listing Agent Scott McNeill Compass

    3 Chesterford Terrace, 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 $2,039,319

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

    64 Westland Ave, 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 $3,118,023

    Last Listing Agent Kim Covino Compass

    257 High St, Winchester, MA 01890
  • /42

    $1,730,000

    Sold Jul 24, 2026

    307 Cross St, Winchester, MA 01890

    • 5 Beds
    • 5 Baths
    • 3,500 Sq Ft
    • Built 1986

    Last Sold Summary

    • 2% Above List Price
    • $494/SF
    • 6 Days On Market

    Current Estimated Value $1,678,133

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

    307 Cross St, Winchester, MA 01890
  • /42

    $1,850,000

    Sold Jan 15, 2026

    77A Brooks St, Winchester, MA 01890

    • 6 Beds
    • 3.5 Baths
    • 4,122 Sq Ft
    • Built 1890

    Last Sold Summary

    • 19% Below List Price
    • $449/SF
    • 35 Days On Market

    Current Estimated Value $1,997,994

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    77A Brooks St, Winchester, MA 01890
  • /24

    $703,000

    Sold Jun 16, 2026

    115 Washington St Unit 2A, Winchester, MA 01890

    • 2 Beds
    • 1 Bath
    • 1,029 Sq Ft
    • Built 1988

    Last Sold Summary

    • 3% Below List Price
    • $683/SF
    • 36 Days On Market

    Current Estimated Value $708,797

    Last Listing Agent Kim Covino Compass

    115 Washington St Unit 2A, Winchester, MA 01890
  • /34

    $2,250,000

    Sold Sep 02, 2026

    6 Davey Ln, Winchester, MA 01890

    • 4 Beds
    • 4 Baths
    • 4,210 Sq Ft
    • Built 1996

    Last Sold Summary

    • 1% Above List Price
    • $534/SF
    • 4 Days On Market

    Current Estimated Value $2,064,267

    Last Listing Agent Gretchen Papineau Coldwell Banker Realty - Andovers/Readings Regional

    6 Davey Ln, 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 $1,906,419

    Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    2 Gershon Way Unit 2, Winchester, MA 01890
  • /41

    $1,820,000

    Sold Sep 10, 2026

    16 Glenwood Ave, Winchester, MA 01890

    • 6 Beds
    • 4.5 Baths
    • 6,900 Sq Ft
    • Built 1966

    Last Sold Summary

    • 17% Below List Price
    • $264/SF
    • 101 Days On Market

    Current Estimated Value $2,091,200

    Last Listing Agent Kim Covino Compass

    16 Glenwood Ave, 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 $1,737,516

    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 $1,856,310

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

    7 Wainwright Rd Unit 13, Winchester, MA 01890
  • /37

    $888,000

    Sold Jun 08, 2026

    9 Governors Ave Unit 2, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 1,799 Sq Ft
    • Built 1903

    Last Sold Summary

    • 1% Below List Price
    • $494/SF
    • 6 Days On Market

    Current Estimated Value $883,967

    Last Listing Agent Philip Vita Compass

    9 Governors Ave Unit 2, Winchester, MA 01890
  • /39

    $3,100,000

    Sold Jul 15, 2026

    27 Everett Ave, Winchester, MA 01890

    • 6 Beds
    • 5.5 Baths
    • 7,431 Sq Ft
    • Built 1905

    Last Sold Summary

    • 14% Below List Price
    • $417/SF
    • 118 Days On Market

    Current Estimated Value $3,249,259

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    27 Everett Ave, Winchester, MA 01890
  • /42

    $2,350,000

    Sold Aug 12, 2026

    50 Brooks St, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 4,403 Sq Ft
    • Built 1988

    Last Sold Summary

    • 9% Below List Price
    • $534/SF
    • 67 Days On Market

    Current Estimated Value $2,402,198

    Last Listing Agent Kim Covino Compass

    50 Brooks St, Winchester, MA 01890
  • /23

    $950,000

    Sold Dec 04, 2025

    16 Park Ave Unit 1, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 1,535 Sq Ft
    • Built 1915

    Last Sold Summary

    • 5% Below List Price
    • $619/SF
    • 26 Days On Market

    Current Estimated Value $952,457

    Last Listing Agent Andrea Mackey The Agency Boston

    16 Park Ave Unit 1, Winchester, MA 01890
  • /38

    $2,600,000

    Sold Jun 18, 2026

    15 York Rd, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 4,500 Sq Ft
    • Built 2017

    Last Sold Summary

    • 4% Above List Price
    • $578/SF
    • 7 Days On Market

    Current Estimated Value $2,501,265

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

    15 York Rd, Winchester, MA 01890
  • /35

    $2,575,000

    Sold May 14, 2026

    2 Abby Rd, Winchester, MA 01890

    • 4 Beds
    • 4.5 Baths
    • 5,614 Sq Ft
    • Built 2024

    Last Sold Summary

    • 3% Below List Price
    • $459/SF
    • 12 Days On Market

    Current Estimated Value $2,591,245

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    2 Abby Rd, Winchester, MA 01890
  • /42

    $2,650,000

    Sold Apr 21, 2026

    45 Bacon St, Winchester, MA 01890

    • 7 Beds
    • 8 Baths
    • 7,043 Sq Ft
    • Built 2011

    Last Sold Summary

    • 11% Below List Price
    • $376/SF
    • 29 Days On Market

    Current Estimated Value $2,814,090

    Last Listing Agent Kim Covino Compass

    45 Bacon St, 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

    $1,830,000

    Sold Feb 26, 2026

    35 Glen Green, Winchester, MA 01890

    • 4 Beds
    • 2 Baths
    • 3,509 Sq Ft
    • Built 1934

    Last Sold Summary

    • 8% Below List Price
    • $522/SF
    • 36 Days On Market

    Current Estimated Value $1,883,181

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    35 Glen Green, Winchester, MA 01890
  • /42

    $1,800,000

    Sold Aug 17, 2026

    18 Graystone Cir Unit 18, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,833 Sq Ft
    • Built 2012

    Last Sold Summary

    • 3% Above List Price
    • $635/SF
    • 1 Day On Market

    Last Listing Agent Kim Covino Compass

    18 Graystone Cir Unit 18, Winchester, MA 01890
  • /42

    $1,330,000

    Sold Apr 14, 2026

    40 Pickering St, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,454 Sq Ft
    • Built 1870

    Last Sold Summary

    • 6% Above List Price
    • $542/SF
    • 0 Days On Market

    Current Estimated Value $1,300,556

    Last Listing Agent Timothy Haynes Keller Williams Realty Signature Properties

    40 Pickering St, Winchester, MA 01890

Showing Results 1 - 40, Page 1 of 8

Frequently Asked Questions

What is the average home price in Winchester, MA?
Homes for sale in Winchester, MA have an average home price of $1,907,933.
What is the average time to sell a house in Winchester, MA?
The houses for sale in Winchester, MA spend an average of 21 days on the market.
What is the number of active homes for sale in Winchester, MA?
There are 37 active homes for sale in Winchester, MA.
How many homes have sold over the last 12 months in Winchester, MA?
175 homes have sold in Winchester, MA over the last 12 months.

Home Price Trends

Median Sale Price
$1,700,000
Median Single Family Sale Price
$1,750,000
Median Townhouse Sale Price
$1,325,000
Median 2 Bedroom Sale Price
$950,000
Average Price Per Sq Ft
$566
Number of Homes for Sale
296
Last 12 months Home Sales
175
Months of Supply
2.50
Median List Price
$1,749,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
2%
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