9,202

Winchester, MA Homes

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  • 171 Swanton St Unit 73, Winchester, MA 01890
    171 Swanton St Unit 73, Winchester, MA 01890
    171 Swanton St Unit 73, Winchester, MA 01890
    /32

    $722,500

    Sold Apr 10, 2026

    171 Swanton St Unit 73, Winchester, MA 01890

    • 2 Beds
    • 2.5 Baths
    • 1,596 Sq Ft
    • Built 1985

    Last Sold Summary

    • 1% Above List Price
    • $453/SF
    • 152 Days On Market

    Current Estimated Value $727,449

    Last Listing Agent John and Maria Reilly JMR Real Estate Group LLC

    171 Swanton St Unit 73, Winchester, MA 01890
    • 20 Winslow Rd, Winchester, MA 01890
      20 Winslow Rd, Winchester, MA 01890
      20 Winslow Rd, Winchester, MA 01890
      /37

      Est $1,941,218

      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

      • 45 Days On Market

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • 9 Prospect St, Winchester, MA 01890
    9 Prospect St, Winchester, MA 01890
    9 Prospect St, Winchester, MA 01890
    /40

    $2,175,000

    Sold Aug 14, 2025

    9 Prospect St, Winchester, MA 01890

    • 6 Beds
    • 3.5 Baths
    • 4,667 Sq Ft
    • Built 1895

    Last Sold Summary

    • 9% Below List Price
    • $466/SF
    • 18 Days On Market

    Current Estimated Value $2,320,952

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    9 Prospect St, Winchester, MA 01890
    • 10 Briarwood Ln, Winchester, MA 01890
      10 Briarwood Ln, Winchester, MA 01890
      10 Briarwood Ln, Winchester, MA 01890
      /41

      Est $2,761,287

      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

      • 0 Days On Market

      Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

  • 6 Alden Ln, Winchester, MA 01890
    6 Alden Ln, Winchester, MA 01890
    6 Alden Ln, Winchester, MA 01890
    /24

    $1,275,000

    Sold Jun 25, 2026

    6 Alden Ln, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 1,511 Sq Ft
    • Built 1949

    Last Sold Summary

    • 2% Below List Price
    • $844/SF
    • 14 Days On Market

    Current Estimated Value $1,327,740

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    6 Alden Ln, Winchester, MA 01890
    • 31 Brooks St, Winchester, MA 01890
      31 Brooks St, Winchester, MA 01890
      31 Brooks St, Winchester, MA 01890
      /40

      Est $2,689,212

      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

      • 4 Days On Market

      Last Listing Agent Kim Covino Compass

  • 1 Fox Hunt Ln, Winchester, MA 01890
    1 Fox Hunt Ln, Winchester, MA 01890
    1 Fox Hunt Ln, Winchester, MA 01890
    /38

    $2,000,000

    Sold Oct 29, 2025

    1 Fox Hunt Ln, Winchester, MA 01890

    • 5 Beds
    • 5 Baths
    • 5,000 Sq Ft
    • Built 1968

    Last Sold Summary

    • 4% Below List Price
    • $400/SF
    • 3 Days On Market

    Current Estimated Value $2,095,211

    Last Listing Agent Leigh Ventura Compass

    1 Fox Hunt Ln, Winchester, MA 01890
    • 27 Brooks St, Winchester, MA 01890
      27 Brooks St, Winchester, MA 01890
      27 Brooks St, Winchester, MA 01890
      /42

      Est $2,522,076

      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

      • 57 Days On Market

      Last Listing Agent Kim Covino Compass

  • 41 Englewood Rd, Winchester, MA 01890
    41 Englewood Rd, Winchester, MA 01890
    41 Englewood Rd, Winchester, MA 01890
    /17

    $1,038,500

    Sold Dec 01, 2025

    41 Englewood Rd, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 1,683 Sq Ft
    • Built 1962

    Last Sold Summary

    • 4% Above List Price
    • $617/SF
    • 8 Days On Market

    Current Estimated Value $1,106,462

    Last Listing Agent Lesley Smith Barrett Sotheby's International Realty

    41 Englewood Rd, Winchester, MA 01890
    • 9 Brooks St, Winchester, MA 01890
      9 Brooks St, Winchester, MA 01890
      9 Brooks St, Winchester, MA 01890
      /42

      Est $2,448,450

      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

      • 35 Days On Market

      Last Listing Agent Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

  • 7 Wainwright Rd Unit 30, Winchester, MA 01890
    7 Wainwright Rd Unit 30, Winchester, MA 01890
    7 Wainwright Rd Unit 30, Winchester, MA 01890
    /31

    $1,350,000

    Sold Jun 22, 2026

    7 Wainwright Rd Unit 30, Winchester, MA 01890

    • 3 Beds
    • 3.5 Baths
    • 2,803 Sq Ft
    • Built 1988

    Last Sold Summary

    • 4% Above List Price
    • $482/SF
    • 1 Day On Market

    Current Estimated Value $1,329,660

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

    7 Wainwright Rd Unit 30, Winchester, MA 01890
    • 19 Sussex Rd, Winchester, MA 01890
      19 Sussex Rd, Winchester, MA 01890
      19 Sussex Rd, Winchester, MA 01890
      /26

      Est $2,162,271

      Not Listed For Sale

      19 Sussex Rd, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 4,023 Sq Ft
      • Built 1998
      19 Sussex Rd, Winchester, MA 01890

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Ida Bianco Coldwell Banker Realty - Lexington

  • 15 Wildwood St, Winchester, MA 01890
    15 Wildwood St, Winchester, MA 01890
    15 Wildwood St, Winchester, MA 01890
    /42

    $2,100,000

    Sold Jun 09, 2026

    15 Wildwood St, Winchester, MA 01890

    • 6 Beds
    • 2.5 Baths
    • 4,104 Sq Ft
    • Built 1900

    Last Sold Summary

    • $512/SF
    • 11 Days On Market

    Current Estimated Value $2,075,976

    Last Listing Agent Kim Covino Compass

    15 Wildwood St, Winchester, MA 01890
    • 5 Hastings Rd, Winchester, MA 01890
      5 Hastings Rd, Winchester, MA 01890
      5 Hastings Rd, Winchester, MA 01890
      /38

      Est $2,044,863

      Not Listed For Sale

      5 Hastings Rd, Winchester, MA 01890

      • 4 Beds
      • 4 Baths
      • 4,195 Sq Ft
      • Built 1995
      5 Hastings Rd, Winchester, MA 01890

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

  • 200 Swanton St Unit 432, Winchester, MA 01890
    200 Swanton St Unit 432, Winchester, MA 01890
    200 Swanton St Unit 432, Winchester, MA 01890
    /21

    $382,000

    Sold Oct 14, 2025

    200 Swanton St Unit 432, Winchester, MA 01890

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

    Last Sold Summary

    • 9% Below List Price
    • $630/SF
    • 28 Days On Market

    Current Estimated Value $381,693

    Last Listing Agent Mark Gilson Keller Williams Realty

    200 Swanton St Unit 432, Winchester, MA 01890
    • 22 Grove Place Unit 30, Winchester, MA 01890
      22 Grove Place Unit 30, Winchester, MA 01890
      22 Grove Place Unit 30, Winchester, MA 01890
      /36

      Est $1,119,810

      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

      • 5 Days On Market

      Last Listing Agent Peter Kasseris Serhant

  • 55 Brookside Ave, Winchester, MA 01890
    55 Brookside Ave, Winchester, MA 01890
    55 Brookside Ave, Winchester, MA 01890
    /14

    $657,500

    Sold Jul 17, 2026

    55 Brookside Ave, Winchester, MA 01890

    • 3 Beds
    • 1 Bath
    • 1,245 Sq Ft
    • Built 1940

    Last Sold Summary

    • 18% Below List Price
    • $528/SF
    • 18 Days On Market

    Current Estimated Value $815,782

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

    55 Brookside Ave, Winchester, MA 01890
    • 22 Grove Place Unit 26, Winchester, MA 01890
      22 Grove Place Unit 26, Winchester, MA 01890
      22 Grove Place Unit 26, Winchester, MA 01890
      /39

      Est $1,138,099

      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

      • 6 Days On Market

      Last Listing Agent Peter Cote Redfin Corp.

  • 4 Winslow Rd, Winchester, MA 01890
    4 Winslow Rd, Winchester, MA 01890
    4 Winslow Rd, Winchester, MA 01890
    /42

    $2,215,000

    Sold Aug 12, 2025

    4 Winslow Rd, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 3,607 Sq Ft
    • Built 1895

    Last Sold Summary

    • 11% Above List Price
    • $614/SF
    • 5 Days On Market

    Current Estimated Value $2,179,778

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    4 Winslow Rd, Winchester, MA 01890
    • 11 Brooks St, Winchester, MA 01890
      11 Brooks St, Winchester, MA 01890
      11 Brooks St, Winchester, MA 01890
      /42

      Est $2,933,486

      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

      • 53 Days On Market

      Last Listing Agent Michaela Mahtani Leading Edge Real Estate

  • 61 Grove St, Winchester, MA 01890
    61 Grove St, Winchester, MA 01890
    61 Grove St, Winchester, MA 01890
    /42

    $2,125,000

    Sold May 06, 2026

    61 Grove St, Winchester, MA 01890

    • 5 Beds
    • 4.5 Baths
    • 4,798 Sq Ft
    • Built 1942

    Last Sold Summary

    • 3% Below List Price
    • $443/SF
    • 54 Days On Market

    Current Estimated Value $2,126,408

    Last Listing Agent Dorothea Feffer Churchill Properties

    61 Grove St, Winchester, MA 01890
    • 37 Canterbury Rd, Winchester, MA 01890
      37 Canterbury Rd, Winchester, MA 01890
      37 Canterbury Rd, Winchester, MA 01890
      /35

      Est $1,732,366

      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

      • 75 Days On Market

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

  • 10 Sheffield W, Winchester, MA 01890
    10 Sheffield W, Winchester, MA 01890
    10 Sheffield W, Winchester, MA 01890
    /42

    $3,470,000

    Sold Mar 18, 2026

    10 Sheffield W, Winchester, MA 01890

    • 5 Beds
    • 6 Baths
    • 6,127 Sq Ft
    • Built 2013

    Last Sold Summary

    • $566/SF
    • 5 Days On Market

    Current Estimated Value $3,464,608

    Last Listing Agent Jay Noble Lamacchia Realty, Inc.

    10 Sheffield W, Winchester, MA 01890
    • 25 Canterbury Rd, Winchester, MA 01890
      25 Canterbury Rd, Winchester, MA 01890
      25 Canterbury Rd, Winchester, MA 01890
      /32

      Est $1,357,490

      Not Listed For Sale

      25 Canterbury Rd, Winchester, MA 01890

      • 4 Beds
      • 1.5 Baths
      • 2,349 Sq Ft
      • Built 1948
      25 Canterbury Rd, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

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

  • 178 Mystic Valley Pkwy, Winchester, MA 01890
    178 Mystic Valley Pkwy, Winchester, MA 01890
    178 Mystic Valley Pkwy, Winchester, MA 01890
    /39

    $1,770,000

    Sold Sep 12, 2025

    178 Mystic Valley Pkwy, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,850 Sq Ft
    • Built 2012

    Last Sold Summary

    • 16% Above List Price
    • $621/SF
    • 4 Days On Market

    Current Estimated Value $1,837,038

    Last Listing Agent Katherine Waters-Clark Compass

    178 Mystic Valley Pkwy, Winchester, MA 01890
    • 47 Grove St, Winchester, MA 01890
      47 Grove St, Winchester, MA 01890
      47 Grove St, Winchester, MA 01890
      /42

      Est $2,477,766

      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

      • 6 Days On Market

      Last Listing Agent Philip Vita Compass

  • 32 Woodside Rd, Winchester, MA 01890
    32 Woodside Rd, Winchester, MA 01890
    32 Woodside Rd, Winchester, MA 01890
    /42

    $1,549,000

    Sold Dec 15, 2025

    32 Woodside Rd, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,587 Sq Ft
    • Built 1933

    Last Sold Summary

    • $599/SF
    • 6 Days On Market

    Current Estimated Value $1,595,719

    Last Listing Agent Kim Covino Compass

    32 Woodside Rd, Winchester, MA 01890
    • 74 Grove St, Winchester, MA 01890
      74 Grove St, Winchester, MA 01890
      74 Grove St, Winchester, MA 01890
      /37

      Est $1,516,629

      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

      • 6 Days On Market

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

  • 40 Sargent Rd, Winchester, MA 01890
    40 Sargent Rd, Winchester, MA 01890
    40 Sargent Rd, Winchester, MA 01890
    /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 $1,363,448

    Last Listing Agent Philip Vita Compass

    40 Sargent Rd, Winchester, MA 01890
    • 11 Wickham Rd, Winchester, MA 01890
      11 Wickham Rd, Winchester, MA 01890
      11 Wickham Rd, Winchester, MA 01890
      /30

      Est $2,726,243

      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

      • 85 Days On Market

      Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

  • 62 Vine St Unit 62, Winchester, MA 01890
    62 Vine St Unit 62, Winchester, MA 01890
    62 Vine St Unit 62, Winchester, MA 01890
    /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 $878,831

    Last Listing Agent David Shorey Real Broker MA, LLC

    62 Vine St Unit 62, Winchester, MA 01890
    • 16 Wickham Rd, Winchester, MA 01890
      16 Wickham Rd, Winchester, MA 01890
      16 Wickham Rd, Winchester, MA 01890
      /42

      Est $2,915,033

      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

      • 8 Days On Market

      Last Listing Agent Rodrigo Serrano Leading Edge Real Estate

  • 112 Church St, Winchester, MA 01890
    112 Church St, Winchester, MA 01890
    112 Church St, Winchester, MA 01890
    /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 $1,691,648

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

    112 Church St, Winchester, MA 01890
    • 15 W Chardon Rd, Winchester, MA 01890
      15 W Chardon Rd, Winchester, MA 01890
      15 W Chardon Rd, Winchester, MA 01890
      /42

      Est $2,765,273

      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

      • 8 Days On Market

      Last Listing Agent Philip Vita Compass

    • 6 Fenwick Rd, Winchester, MA 01890
      6 Fenwick Rd, Winchester, MA 01890
      6 Fenwick Rd, Winchester, MA 01890
      /40

      Est $1,897,272

      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

      • 3 Days On Market

      Last Listing Agent Kim Covino Compass

    • 14 Grove St, Winchester, MA 01890
      14 Grove St, Winchester, MA 01890
      14 Grove St, Winchester, MA 01890
      /42

      Est $2,057,044

      Not Listed For Sale

      14 Grove St, Winchester, MA 01890

      • 5 Beds
      • 4 Baths
      • 4,744 Sq Ft
      • Built 1922
      14 Grove St, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Kim Covino Compass

    • 22 Grove St, Winchester, MA 01890
      22 Grove St, Winchester, MA 01890
      22 Grove St, Winchester, MA 01890
      /40

      Est $1,909,416

      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

      • 4 Days On Market

      Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    • 45 Brooks St, Winchester, MA 01890
      45 Brooks St, Winchester, MA 01890
      45 Brooks St, Winchester, MA 01890
      /41

      Est $2,610,492

      Not Listed For Sale

      45 Brooks St, Winchester, MA 01890

      • 4 Beds
      • 4 Baths
      • 4,325 Sq Ft
      • Built 1953
      45 Brooks St, Winchester, MA 01890

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Kim Covino Compass

    • 18 Town Way, Winchester, MA 01890
      18 Town Way, Winchester, MA 01890
      18 Town Way, Winchester, MA 01890
      /42

      Est $2,209,943

      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

      • 10 Days On Market

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

    • 350 S Border Rd, Winchester, MA 01890
      350 S Border Rd, Winchester, MA 01890
      350 S Border Rd, Winchester, MA 01890
      /30

      Est $1,365,124

      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

      • 25 Days On Market

      Last Listing Agent Jill Fitzpatrick Century 21 North East

Showing Results 601 - 640, Page 16 of 18

Massachusetts Middlesex County

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