9,208

Winchester, MA Homes

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  • /31

    $948,000 Sold May 29, 2025

    79 Sylvester Ave, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 1,469 Sq Ft
    • Built 1928

    Last Sold Summary

    • 9% Above List Price
    • $645/SF
    • 5 Days On Market

    Current Estimated Value $947,982

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    79 Sylvester Ave, Winchester, MA 01890
    • /32

      Est $1,201,535 Not Listed For Sale

      89 Mystic Valley Pkwy, Winchester, MA 01890

      • 5 Beds
      • 2.5 Baths
      • 3,220 Sq Ft
      • Built 1900
      89 Mystic Valley Pkwy, Winchester, MA 01890

      Last Sold Summary

      • 11% Above List Price
      • $335/SF
      • 105 Days On Market
      • Last Sold Price $1,080,000
      • Jan 08, 2025

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

  • /39

    $1,475,000 Sold Sep 26, 2025

    60 Graystone Cir Unit 60, Winchester, MA 01890

    • 2 Beds
    • 2.5 Baths
    • 1,947 Sq Ft
    • Built 2011

    Last Sold Summary

    • 2% Below List Price
    • $758/SF
    • 7 Days On Market

    Current Estimated Value $1,542,178

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

    60 Graystone Cir Unit 60, Winchester, MA 01890
    • /42

      Est $1,519,777 Not Listed For Sale

      410 Main St, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 2,075 Sq Ft
      • Built 1900
      410 Main St, Winchester, MA 01890

      Last Sold Summary

      • 5% Below List Price
      • $771/SF
      • 6 Days On Market
      • Last Sold Price $1,600,000
      • Mar 03, 2025

      Last Listing Agent Anne Spry Barrett Sotheby's International Realty

  • /22

    $4,200,000 Sold Jun 26, 2025

    3 Foxcroft Rd, Winchester, MA 01890

    • 6 Beds
    • 5.5 Baths
    • 5,208 Sq Ft
    • Built 2025

    Last Sold Summary

    • $806/SF
    • 4 Days On Market

    Current Estimated Value $3,828,981

    Last Listing Agent Kim Covino Compass

    3 Foxcroft Rd, Winchester, MA 01890
    • /29

      Est $1,649,394 Not Listed For Sale

      48 Lloyd St, Winchester, MA 01890

      • 5 Beds
      • 2.5 Baths
      • 2,747 Sq Ft
      • Built 1915
      48 Lloyd St, Winchester, MA 01890

      Last Sold Summary

      • 13% Above List Price
      • $530/SF
      • 7 Days On Market
      • Last Sold Price $1,455,000
      • Jun 16, 2023

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

  • /37

    $1,290,000 Sold Dec 05, 2025

    40 Sargent Rd, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 1,492 Sq Ft
    • Built 1935

    Last Sold Summary

    • 4% Below List Price
    • $865/SF
    • 21 Days On Market

    Current Estimated Value $1,282,698

    Last Listing Agent Philip Vita Compass

    40 Sargent Rd, Winchester, MA 01890
    • /37

      Est $1,939,231 Not Listed For Sale

      20 Winslow Rd, Winchester, MA 01890

      • 4 Beds
      • 5 Baths
      • 3,522 Sq Ft
      • Built 1926
      20 Winslow Rd, Winchester, MA 01890

      Last Sold Summary

      • 12% Above List Price
      • $490/SF
      • 45 Days On Market
      • Last Sold Price $1,725,000
      • Sep 27, 2023

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • /39

    $800,000 Sold Oct 24, 2025

    62 Vine St Unit 62, Winchester, MA 01890

    • 2 Beds
    • 2 Baths
    • 1,545 Sq Ft
    • Built 1982

    Last Sold Summary

    • $518/SF
    • 5 Days On Market

    Current Estimated Value $836,867

    Last Listing Agent David Shorey Real Broker MA, LLC

    62 Vine St Unit 62, Winchester, MA 01890
    • /41

      Est $2,768,901 Not Listed For Sale

      10 Briarwood Ln, Winchester, MA 01890

      • 6 Beds
      • 5.5 Baths
      • 5,171 Sq Ft
      • Built 1998
      10 Briarwood Ln, Winchester, MA 01890

      Last Sold Summary

      • 2% Above List Price
      • $527/SF
      • 0 Days On Market
      • Last Sold Price $2,725,000
      • Aug 26, 2024

      Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

  • /40

    $1,600,000 Sold Nov 07, 2025

    112 Church St, Winchester, MA 01890

    • 8 Beds
    • 2.5 Baths
    • 3,591 Sq Ft
    • Built 1880

    Last Sold Summary

    • 3% Below List Price
    • $446/SF
    • 8 Days On Market

    Current Estimated Value $1,632,497

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

    112 Church St, Winchester, MA 01890
    • /40

      Est $2,676,869 Not Listed For Sale

      31 Brooks St, Winchester, MA 01890

      • 6 Beds
      • 3.5 Baths
      • 4,822 Sq Ft
      • Built 1994
      31 Brooks St, Winchester, MA 01890

      Last Sold Summary

      • 1% Above List Price
      • $550/SF
      • 4 Days On Market
      • Last Sold Price $2,650,000
      • May 08, 2024

      Last Listing Agent Kim Covino Compass

  • /40

    $1,877,000 Sold Jun 30, 2025

    20 Seneca Rd, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 2,813 Sq Ft
    • Built 1930

    Last Sold Summary

    • 6% Below List Price
    • $667/SF
    • 26 Days On Market

    Current Estimated Value $1,860,985

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

    20 Seneca Rd, Winchester, MA 01890
    • /42

      Est $2,539,543 Not Listed For Sale

      27 Brooks St, Winchester, MA 01890

      • 4 Beds
      • 4 Baths
      • 4,650 Sq Ft
      • Built 1992
      27 Brooks St, Winchester, MA 01890

      Last Sold Summary

      • 10% Above List Price
      • $497/SF
      • 57 Days On Market
      • Last Sold Price $2,312,500
      • Dec 20, 2023

      Last Listing Agent Kim Covino Compass

    • /42

      Est $2,444,123 Not Listed For Sale

      9 Brooks St, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 4,278 Sq Ft
      • Built 1992
      9 Brooks St, Winchester, MA 01890

      Last Sold Summary

      • 4% Above List Price
      • $550/SF
      • 35 Days On Market
      • Last Sold Price $2,355,000
      • Oct 03, 2024

      Last Listing Agent Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

    • /36

      Est $1,206,802 Not Listed For Sale

      22 Grove Place Unit 30, Winchester, MA 01890

      • 3 Beds
      • 3 Baths
      • 3,045 Sq Ft
      • Built 1986
      22 Grove Place Unit 30, Winchester, MA 01890

      Last Sold Summary

      • 18% Above List Price
      • $337/SF
      • 5 Days On Market
      • Last Sold Price $1,025,000
      • Dec 23, 2024

      Last Listing Agent Peter Kasseris Serhant

    • /14

      Est $797,956 Not Listed For Sale

      22 Grove Place Unit 29, Winchester, MA 01890

      • 2 Beds
      • 1.5 Baths
      • 1,530 Sq Ft
      • Built 1986
      22 Grove Place Unit 29, Winchester, MA 01890

      Last Sold Summary

      • 30% Above List Price
      • $402/SF
      • 3 Days On Market
      • Last Sold Price $615,000
      • May 16, 2023

      Last Listing Agent Sally Baldwin Coldwell Banker Realty - Lexington

    • /39

      Est $1,126,627 Not Listed For Sale

      22 Grove Place Unit 26, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 3,045 Sq Ft
      • Built 1986
      22 Grove Place Unit 26, Winchester, MA 01890

      Last Sold Summary

      • 12% Above List Price
      • $330/SF
      • 6 Days On Market
      • Last Sold Price $1,006,000
      • Nov 13, 2023

      Last Listing Agent Peter Cote Redfin Corp.

    • /42

      Est $2,836,494 Not Listed For Sale

      11 Brooks St, Winchester, MA 01890

      • 5 Beds
      • 4.5 Baths
      • 5,208 Sq Ft
      • Built 2023
      11 Brooks St, Winchester, MA 01890

      Last Sold Summary

      • 3% Above List Price
      • $528/SF
      • 53 Days On Market
      • Last Sold Price $2,750,000
      • May 21, 2024

      Last Listing Agent Michaela Mahtani Leading Edge Real Estate

    • /35

      Est $1,694,307 Not Listed For Sale

      37 Canterbury Rd, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 3,527 Sq Ft
      • Built 1948
      37 Canterbury Rd, Winchester, MA 01890

      Last Sold Summary

      • 10% Above List Price
      • $435/SF
      • 75 Days On Market
      • Last Sold Price $1,536,000
      • Jun 21, 2024

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

    • /42

      Est $2,462,030 Not Listed For Sale

      47 Grove St, Winchester, MA 01890

      • 4 Beds
      • 4.5 Baths
      • 4,635 Sq Ft
      • Built 2024
      47 Grove St, Winchester, MA 01890

      Last Sold Summary

      • 3% Above List Price
      • $518/SF
      • 6 Days On Market
      • Last Sold Price $2,400,000
      • Apr 04, 2024

      Last Listing Agent Philip Vita Compass

    • /37

      Est $1,459,054 Not Listed For Sale

      74 Grove St, Winchester, MA 01890

      • 4 Beds
      • 2 Baths
      • 2,946 Sq Ft
      • Built 1942
      74 Grove St, Winchester, MA 01890

      Last Sold Summary

      • 9% Above List Price
      • $453/SF
      • 6 Days On Market
      • Last Sold Price $1,336,000
      • Apr 11, 2024

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

    • /30

      Est $2,740,739 Not Listed For Sale

      11 Wickham Rd, Winchester, MA 01890

      • 4 Beds
      • 5 Baths
      • 4,750 Sq Ft
      • Built 2007
      11 Wickham Rd, Winchester, MA 01890

      Last Sold Summary

      • 2% Above List Price
      • $568/SF
      • 85 Days On Market
      • Last Sold Price $2,700,000
      • Nov 02, 2023

      Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    • /42

      Est $2,903,323 Not Listed For Sale

      16 Wickham Rd, Winchester, MA 01890

      • 5 Beds
      • 6 Baths
      • 5,850 Sq Ft
      • Built 2018
      16 Wickham Rd, Winchester, MA 01890

      Last Sold Summary

      • 3% Above List Price
      • $483/SF
      • 8 Days On Market
      • Last Sold Price $2,825,000
      • Feb 25, 2025

      Last Listing Agent Rodrigo Serrano Leading Edge Real Estate

    • /40

      Est $1,479,789 Not Listed For Sale

      19 W Chardon Rd, Winchester, MA 01890

      • 4 Beds
      • 1.5 Baths
      • 1,922 Sq Ft
      • Built 1957
      19 W Chardon Rd, Winchester, MA 01890

      Last Sold Summary

      • 8% Above List Price
      • $715/SF
      • 6 Days On Market
      • Last Sold Price $1,375,000
      • Jul 06, 2023

      Last Listing Agent Michaela Mahtani Leading Edge Real Estate

    • /42

      Est $2,683,979 Not Listed For Sale

      15 W Chardon Rd, Winchester, MA 01890

      • 6 Beds
      • 5.5 Baths
      • 5,896 Sq Ft
      • Built 2024
      15 W Chardon Rd, Winchester, MA 01890

      Last Sold Summary

      • 11% Below List Price
      • $510/SF
      • 8 Days On Market
      • Last Sold Price $3,005,000
      • Oct 25, 2024

      Last Listing Agent Philip Vita Compass

    • /40

      Est $1,921,673 Not Listed For Sale

      6 Fenwick Rd, Winchester, MA 01890

      • 5 Beds
      • 3.5 Baths
      • 2,809 Sq Ft
      • Built 1910
      6 Fenwick Rd, Winchester, MA 01890

      Last Sold Summary

      • 2% Above List Price
      • $673/SF
      • 3 Days On Market
      • Last Sold Price $1,890,000
      • Aug 30, 2024

      Last Listing Agent Kim Covino Compass

    • /40

      Est $1,933,244 Not Listed For Sale

      22 Grove St, Winchester, MA 01890

      • 5 Beds
      • 3 Baths
      • 3,324 Sq Ft
      • Built 1951
      22 Grove St, Winchester, MA 01890

      Last Sold Summary

      • 6% Above List Price
      • $549/SF
      • 4 Days On Market
      • Last Sold Price $1,825,000
      • Feb 28, 2024

      Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    • /42

      Est $2,207,327 Not Listed For Sale

      18 Town Way, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 4,026 Sq Ft
      • Built 2006
      18 Town Way, Winchester, MA 01890

      Last Sold Summary

      • 2% Below List Price
      • $559/SF
      • 10 Days On Market
      • Last Sold Price $2,250,000
      • Nov 20, 2024

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

    • /30

      Est $1,254,740 Not Listed For Sale

      350 S Border Rd, Winchester, MA 01890

      • 3 Beds
      • 2.5 Baths
      • 2,240 Sq Ft
      • Built 1966
      350 S Border Rd, Winchester, MA 01890

      Last Sold Summary

      • 9% Above List Price
      • $512/SF
      • 25 Days On Market
      • Last Sold Price $1,148,000
      • Jul 10, 2024

      Last Listing Agent Jill Fitzpatrick Century 21 North East

    • /35

      Est $1,281,359 Not Listed For Sale

      155 Main St, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 2,441 Sq Ft
      • Built 1964
      155 Main St, Winchester, MA 01890

      Last Sold Summary

      • 11% Above List Price
      • $471/SF
      • 7 Days On Market
      • Last Sold Price $1,150,000
      • Aug 07, 2023

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

    • /34

      Est $1,478,334 Not Listed For Sale

      9 Everell Rd, Winchester, MA 01890

      • 4 Beds
      • 2 Baths
      • 2,251 Sq Ft
      • Built 1937
      9 Everell Rd, Winchester, MA 01890

      Last Sold Summary

      • 6% Above List Price
      • $622/SF
      • 6 Days On Market
      • Last Sold Price $1,400,000
      • Apr 11, 2024

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

    • /34

      Est $1,525,109 Not Listed For Sale

      20 Stowell Rd, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 2,314 Sq Ft
      • Built 1928
      20 Stowell Rd, Winchester, MA 01890

      Last Sold Summary

      • 9% Above List Price
      • $605/SF
      • 7 Days On Market
      • Last Sold Price $1,400,000
      • Jul 07, 2023

      Last Listing Agent Elena Langlois Compass

    • /42

      Est $1,851,474 Not Listed For Sale

      26 Stowell Rd, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 2,816 Sq Ft
      • Built 1934
      26 Stowell Rd, Winchester, MA 01890

      Last Sold Summary

      • 3% Below List Price
      • $675/SF
      • 6 Days On Market
      • Last Sold Price $1,900,000
      • Jul 10, 2024

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

    • /39

      Est $2,175,115 Not Listed For Sale

      445 Highland Ave, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 3,588 Sq Ft
      • Built 2002
      445 Highland Ave, Winchester, MA 01890

      Last Sold Summary

      • 9% Above List Price
      • $555/SF
      • 6 Days On Market
      • Last Sold Price $1,990,000
      • Jun 29, 2023

      Last Listing Agent Elena Langlois Compass

    • /40

      Est $1,100,724 Not Listed For Sale

      437 Highland Ave, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 1,589 Sq Ft
      • Built 1930
      437 Highland Ave, Winchester, MA 01890

      Last Sold Summary

      • 17% Above List Price
      • $590/SF
      • 19 Days On Market
      • Last Sold Price $937,000
      • Sep 06, 2023

      Last Listing Agent Gayle Winters Compass

    • /3

      Est $1,548,315 Not Listed For Sale

      12 Everell Rd, Winchester, MA 01890

      • 3 Beds
      • 2.5 Baths
      • 2,212 Sq Ft
      • Built 1920
      12 Everell Rd, Winchester, MA 01890

      Last Sold Summary

      • 4% Below List Price
      • $728/SF
      • 6 Days On Market
      • Last Sold Price $1,610,000
      • Aug 15, 2024

      Last Listing Agent Quinn Simpson Compass

    • /31

      Est $2,132,875 Not Listed For Sale

      1 Marshall Rd, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 3,380 Sq Ft
      • Built 1927
      1 Marshall Rd, Winchester, MA 01890

      Last Sold Summary

      • 12% Above List Price
      • $562/SF
      • 66 Days On Market
      • Last Sold Price $1,899,000
      • Sep 07, 2023

      Last Listing Agent Mark Donnellan Gibson Sotheby's International Realty

    • /42

      Est $1,743,112 Not Listed For Sale

      16 Marshall Rd, Winchester, MA 01890

      • 4 Beds
      • 3 Baths
      • 2,866 Sq Ft
      • Built 1951
      16 Marshall Rd, Winchester, MA 01890

      Last Sold Summary

      • 8% Above List Price
      • $564/SF
      • 3 Days On Market
      • Last Sold Price $1,615,000
      • Oct 27, 2023

      Last Listing Agent The Petrowsky Jones Group Compass

    • /36

      Est $1,926,557 Not Listed For Sale

      10 Marshall Rd, Winchester, MA 01890

      • 5 Beds
      • 3.5 Baths
      • 3,376 Sq Ft
      • Built 1925
      10 Marshall Rd, Winchester, MA 01890

      Last Sold Summary

      • 3% Above List Price
      • $555/SF
      • 28 Days On Market
      • Last Sold Price $1,875,000
      • Dec 23, 2024

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

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