315

Recently Sold Winchester, MA 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
  • /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
  • /36

    $1,175,000

    Sold Aug 18, 2025

    163 Main St, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,335 Sq Ft
    • Built 1961

    Last Sold Summary

    • 18% Above List Price
    • $503/SF
    • 8 Days On Market

    Current Estimated Value $1,234,591

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    163 Main St, 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
  • /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
  • /2

    $720,000

    Sold Aug 26, 2025

    29 Vine St Unit 7, Winchester, MA 01890

    • 2 Beds
    • 1.5 Baths
    • 1,300 Sq Ft
    • Built 1980

    Last Sold Summary

    • 3% Above List Price
    • $554/SF
    • 4 Days On Market

    Current Estimated Value $742,851

    Last Listing Agent Philip Vita Compass

    29 Vine St Unit 7, 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
  • /42

    $3,174,500

    Sold Sep 02, 2025

    18 Wickham Rd, Winchester, MA 01890

    • 6 Beds
    • 5 Baths
    • 7,005 Sq Ft
    • Built 2022

    Last Sold Summary

    • 2% Below List Price
    • $453/SF
    • 9 Days On Market

    Current Estimated Value $3,282,100

    Last Listing Agent Philip Vita Compass

    18 Wickham Rd, 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
  • /41

    $1,510,000

    Sold Sep 02, 2025

    155 Highland Ave, Winchester, MA 01890

    • 5 Beds
    • 2.5 Baths
    • 1,965 Sq Ft
    • Built 1900

    Last Sold Summary

    • 13% Above List Price
    • $768/SF
    • 8 Days On Market

    Current Estimated Value $1,524,849

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

    155 Highland Ave, 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
  • /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 $1,787,828

    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 $3,118,023

    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
  • /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 $1,902,667

    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 $1,737,516

    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
  • /40

    $1,160,000

    Sold Aug 14, 2025

    518 Washington St, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,302 Sq Ft
    • Built 1915

    Last Sold Summary

    • 3% Below List Price
    • $504/SF
    • 22 Days On Market

    Current Estimated Value $1,231,718

    Last Listing Agent Rodrigo Serrano Leading Edge Real Estate

    518 Washington 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 $974,620

    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 $2,494,290

    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 $2,601,690

    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

    $1,330,000

    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
  • /42

    $2,890,000

    Sold Aug 14, 2025

    21 Fernway, Winchester, MA 01890

    • 5 Beds
    • 4.5 Baths
    • 5,386 Sq Ft
    • Built 1963

    Last Sold Summary

    • $537/SF
    • 9 Days On Market

    Current Estimated Value $2,969,905

    Last Listing Agent Kim Covino Compass

    21 Fernway, Winchester, MA 01890
  • /30

    $900,000

    Sold Oct 20, 2025

    171 Swanton St Unit 5, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 1,843 Sq Ft
    • Built 1984

    Last Sold Summary

    • 3% Above List Price
    • $488/SF
    • 8 Days On Market

    Current Estimated Value $923,879

    Last Listing Agent Jonathan Radford Coldwell Banker Realty - Boston

    171 Swanton St Unit 5, 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 $1,884,953.
What is the average time to sell a house in Winchester, MA?
The houses for sale in Winchester, MA spend an average of 20 days on the market.
What is the number of active homes for sale in Winchester, MA?
There are 29 active homes for sale in Winchester, MA.
How many homes have sold over the last 12 months in Winchester, MA?
181 homes have sold in Winchester, MA over the last 12 months.

Home Price Trends

Median Sale Price
$1,678,500
Median Single Family Sale Price
$1,750,000
Median Townhouse Sale Price
$1,412,500
Median 2 Bedroom Sale Price
$940,000
Average Price Per Sq Ft
$565
Number of Homes for Sale
29
Last 12 months Home Sales
181
Months of Supply
1.90
Median List Price
$1,725,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
0%
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