311

Recently Sold Winchester, MA Homes

Section Image
  • /39

    $950,000

    Sold Jul 17, 2025

    6 Francis Circuit Unit 6, Winchester, MA 01890

    • 2 Beds
    • 2 Baths
    • 1,540 Sq Ft
    • Built 1875

    Last Sold Summary

    • 1% Below List Price
    • $617/SF
    • 10 Days On Market

    Last Listing Agent Katherine Waters-Clark Compass

    6 Francis Circuit Unit 6, Winchester, MA 01890
  • /41

    $2,850,000

    Sold Jun 09, 2025

    45 Brooks St, Winchester, MA 01890

    • 4 Beds
    • 4 Baths
    • 4,325 Sq Ft
    • Built 1953

    Last Sold Summary

    • 2% Below List Price
    • $659/SF
    • 8 Days On Market

    Current Estimated Value $2,833,523

    Last Listing Agent Kim Covino Compass

    45 Brooks St, 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 $1,234,197

    Last Listing Agent Kim Covino Compass

    12 Thornberry Rd, Winchester, MA 01890
  • /39

    $2,200,000

    Sold Jun 30, 2025

    1 Saint Augustine Ct, Winchester, MA 01890

    • 4 Beds
    • 4 Baths
    • 3,818 Sq Ft
    • Built 1967

    Last Sold Summary

    • 10% Above List Price
    • $576/SF
    • 0 Days On Market

    Current Estimated Value $2,140,394

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    1 Saint Augustine Ct, 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 $1,385,851

    Last Listing Agent Kim Covino Compass

    104 Church St, 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 $1,644,788

    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 $1,227,282

    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 $1,208,480

    Last Listing Agent Gayle Winters Compass

    7 Trinity 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 $1,950,809

    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 $1,574,903

    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 $752,486

    Last Listing Agent Philip Vita Compass

    29 Vine St Unit 7, 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 $3,271,880

    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 $481,136

    Last Listing Agent Rameel Rana Advise Realty

    22 Oak St, Winchester, MA 01890
  • /28

    $1,260,000

    Sold Jun 30, 2025

    261 Cambridge St Unit 261 G, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,705 Sq Ft
    • Built 1885

    Last Sold Summary

    • 3% Below List Price
    • $466/SF
    • 41 Days On Market

    Current Estimated Value $1,486,903

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

    261 Cambridge St Unit 261 G, Winchester, MA 01890
  • /37

    $1,390,000

    Sold Jul 15, 2025

    26 Ridge St, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,388 Sq Ft
    • Built 1963

    Last Sold Summary

    • 1% Above List Price
    • $582/SF
    • 6 Days On Market

    Current Estimated Value $1,436,052

    Last Listing Agent Dream Team Dreamega International Realty LLC

    26 Ridge 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 $1,545,038

    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 $2,042,361

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

    64 Westland Ave, Winchester, MA 01890
  • /25

    $715,000

    Sold Jun 27, 2025

    7 Conant Rd Unit 37, Winchester, MA 01890

    • 2 Beds
    • 2.5 Baths
    • 1,539 Sq Ft
    • Built 1999

    Last Sold Summary

    • 5% Below List Price
    • $465/SF
    • 33 Days On Market

    Current Estimated Value $740,182

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

    7 Conant Rd Unit 37, Winchester, MA 01890
  • /19

    $690,000

    Sold Jun 06, 2025

    7 Conant Rd Unit 60, Winchester, MA 01890

    • 2 Beds
    • 2.5 Baths
    • 1,634 Sq Ft
    • Built 1999

    Last Sold Summary

    • 6% Below List Price
    • $422/SF
    • 20 Days On Market

    Current Estimated Value $739,895

    Last Listing Agent Irene Novia Loka Matahari Real Estate LLC

    7 Conant Rd Unit 60, 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 $1,825,321

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

    5 Thornton Rd, Winchester, MA 01890
  • /42

    $1,540,000

    Sold Jul 11, 2025

    21 Johnson Rd, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,814 Sq Ft
    • Built 1970

    Last Sold Summary

    • 1% Above List Price
    • $547/SF
    • 5 Days On Market

    Current Estimated Value $1,569,630

    Last Listing Agent Stefanie Clifford Keller Williams Realty Boston Northwest

    21 Johnson 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 $3,191,342

    Last Listing Agent Kim Covino Compass

    257 High 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 $1,932,535

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    77A Brooks St, 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 $1,872,868

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

    7 Wainwright Rd Unit 13, 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 $1,221,680

    Last Listing Agent Rodrigo Serrano Leading Edge Real Estate

    518 Washington St, Winchester, MA 01890
  • /41

    $2,425,000

    Sold Jul 31, 2025

    15 Churchill Rd, Winchester, MA 01890

    • 4 Beds
    • 4.5 Baths
    • 5,501 Sq Ft
    • Built 2025

    Last Sold Summary

    • 7% Below List Price
    • $441/SF
    • 61 Days On Market

    Current Estimated Value $2,466,164

    Last Listing Agent Kim Covino Compass

    15 Churchill Rd, 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 $979,062

    Last Listing Agent Andrea Mackey The Agency Boston

    16 Park Ave Unit 1, 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 $2,646,202

    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 $2,800,406

    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 $1,764,234

    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 $1,874,372

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    35 Glen Green, Winchester, MA 01890
  • /15

    $930,000

    Sold Jun 20, 2025

    48 Tremont St, Winchester, MA 01890

    • 4 Beds
    • 3 Baths
    • 2,333 Sq Ft
    • Built 1959

    Last Sold Summary

    • 7% Below List Price
    • $399/SF
    • 25 Days On Market

    Current Estimated Value $1,012,554

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

    48 Tremont St, 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 $1,288,673

    Last Listing Agent Timothy Haynes Keller Williams Realty Signature Properties

    40 Pickering St, Winchester, MA 01890
  • /35

    $1,750,000

    Sold Jun 17, 2025

    18 Englewood Rd, Winchester, MA 01890

    • 5 Beds
    • 2.5 Baths
    • 2,597 Sq Ft
    • Built 1925

    Last Sold Summary

    • 6% Above List Price
    • $674/SF
    • 2 Days On Market

    Current Estimated Value $1,737,420

    Last Listing Agent Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

    18 Englewood Rd, 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 $2,972,365

    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 $922,275

    Last Listing Agent Jonathan Radford Coldwell Banker Realty - Boston

    171 Swanton St Unit 5, Winchester, MA 01890
  • /32

    $868,000

    Sold Sep 04, 2025

    235 Cross St, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 1,931 Sq Ft
    • Built 1956

    Last Sold Summary

    • 16% Above List Price
    • $450/SF
    • 8 Days On Market

    Current Estimated Value $927,917

    Last Listing Agent Melanie Lentini Leading Edge Real Estate

    235 Cross 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 $1,867,835.
What is the average time to sell a house in Winchester, MA?
The houses for sale in Winchester, MA spend an average of 22 days on the market.
What is the number of active homes for sale in Winchester, MA?
There are 33 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 Prices in Winchester, MA

Home Price Trends

Median Sale Price
$1,558,200
Median Single Family Sale Price
$1,737,500
Median Townhouse Sale Price
$1,300,000
Median 2 Bedroom Sale Price
$940,000
Average Price Per Sq Ft
$559
Number of Homes for Sale
33
Last 12 months Home Sales
181
Months of Supply
2.20
Median List Price
$1,612,500
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-8%
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