9,208

Winchester, MA Homes

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  • /40

    $1,510,000 Sold Jun 09, 2025

    7 Hutchinson Rd, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 3,406 Sq Ft
    • Built 1959

    Last Sold Summary

    • 10% Above List Price
    • $443/SF
    • 5 Days On Market

    Current Estimated Value $1,560,916

    Last Listing Agent Kim Covino Compass

    7 Hutchinson Rd, Winchester, MA 01890
    • /22

      Est $369,363 Not Listed For Sale

      200 Swanton St Unit 322, Winchester, MA 01890

      • 1 Bed
      • 1 Bath
      • 606 Sq Ft
      • Built 1966
      200 Swanton St Unit 322, Winchester, MA 01890

      Last Sold Summary

      • 2% Above List Price
      • $598/SF
      • 24 Days On Market
      • Last Sold Price $362,500
      • Apr 30, 2024

      Last Listing Agent Matthew Basteri Flow Realty, Inc.

  • /42

    $4,065,000 Sold May 16, 2025

    6 Vinson Cir, Winchester, MA 01890

    • 6 Beds
    • 7.5 Baths
    • 7,500 Sq Ft
    • Built 2025

    Last Sold Summary

    • 3% Below List Price
    • $542/SF
    • 71 Days On Market

    Current Estimated Value $4,023,127

    Last Listing Agent Peter Kasseris Serhant

    6 Vinson Cir, Winchester, MA 01890
    • /16

      Est $293,104 Not Listed For Sale

      200 Swanton St Unit T32, Winchester, MA 01890

      • 1 Bed
      • 1 Bath
      • 450 Sq Ft
      • Built 1966
      200 Swanton St Unit T32, Winchester, MA 01890

      Last Sold Summary

      • 17% Above List Price
      • $556/SF
      • 17 Days On Market
      • Last Sold Price $250,000
      • Apr 27, 2023

      Last Listing Agent Joan Powell RE/MAX

  • /6

    $1,120,000 Sold Aug 11, 2025

    540-542 Washington St, Winchester, MA 01890

    • 4 Beds
    • 2 Baths
    • 2,060 Sq Ft
    • Built 1917

    Last Sold Summary

    • 2% Above List Price
    • $544/SF
    • 2 Days On Market

    Last Listing Agent Wei Wang WW Real Estate LLC

    540-542 Washington St, Winchester, MA 01890
    • /19

      Est $365,099 Not Listed For Sale

      200 Swanton St Unit T26, Winchester, MA 01890

      • 1 Bed
      • 1 Bath
      • 634 Sq Ft
      • Built 1966
      200 Swanton St Unit T26, Winchester, MA 01890

      Last Sold Summary

      • 3% Below List Price
      • $595/SF
      • 5 Days On Market
      • Last Sold Price $377,000
      • Dec 02, 2024

      Last Listing Agent Gretchen Chingris

  • /33

    $1,470,000 Sold Mar 25, 2026

    2 Canterbury Rd, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,370 Sq Ft
    • Built 1940

    Last Sold Summary

    • 5% Above List Price
    • $620/SF
    • 8 Days On Market

    Current Estimated Value $1,394,560

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

    2 Canterbury Rd, Winchester, MA 01890
    • /19

      Est $292,837 Not Listed For Sale

      200 Swanton St Unit T8, Winchester, MA 01890

      • 1 Bed
      • 1 Bath
      • 450 Sq Ft
      • Built 1966
      200 Swanton St Unit T8, Winchester, MA 01890

      Last Sold Summary

      • 6% Above List Price
      • $616/SF
      • 13 Days On Market
      • Last Sold Price $277,000
      • Oct 31, 2024

      Last Listing Agent Kim Covino Compass

  • /40

    $2,250,000 Sold Dec 11, 2025

    14 Grant Rd, Winchester, MA 01890

    • 6 Beds
    • 4.5 Baths
    • 4,200 Sq Ft
    • Built 2025

    Last Sold Summary

    • 4% Below List Price
    • $536/SF
    • 26 Days On Market

    Current Estimated Value $2,255,047

    Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    14 Grant Rd, Winchester, MA 01890
    • /12

      Est $340,891 Not Listed For Sale

      200 Swanton St Unit L32, Winchester, MA 01890

      • 1 Bed
      • 1 Bath
      • 602 Sq Ft
      • Built 1966
      200 Swanton St Unit L32, Winchester, MA 01890

      Last Sold Summary

      • 3% Below List Price
      • $581/SF
      • 19 Days On Market
      • Last Sold Price $350,000
      • Nov 05, 2024

      Last Listing Agent Joan Powell RE/MAX

  • /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 $722,943

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

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

      Est $345,436 Not Listed For Sale

      200 Swanton St Unit L30, Winchester, MA 01890

      • 1 Bed
      • 1 Bath
      • 602 Sq Ft
      • Built 1966
      200 Swanton St Unit L30, Winchester, MA 01890

      Last Sold Summary

      • 4% Below List Price
      • $598/SF
      • 39 Days On Market
      • Last Sold Price $360,000
      • Mar 14, 2024

      Last Listing Agent Mary Lou Bigelow Gibson Sotheby's International Realty

  • /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 $2,277,655

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    9 Prospect St, Winchester, MA 01890
    • /23

      Est $374,926 Not Listed For Sale

      200 Swanton St Unit L25, Winchester, MA 01890

      • 1 Bed
      • 1 Bath
      • 602 Sq Ft
      • Built 1966
      200 Swanton St Unit L25, Winchester, MA 01890

      Last Sold Summary

      • 7% Above List Price
      • $581/SF
      • 5 Days On Market
      • Last Sold Price $350,000
      • Apr 01, 2024

      Last Listing Agent Ai Cheng Goh Z. Realty

  • /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 $2,027,309

    Last Listing Agent Leigh Ventura Compass

    1 Fox Hunt Ln, Winchester, MA 01890
    • /32

      Est $1,207,148 Not Listed For Sale

      79 Oak St, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 1,965 Sq Ft
      • Built 1879
      79 Oak St, Winchester, MA 01890

      Last Sold Summary

      • 4% Below List Price
      • $642/SF
      • 56 Days On Market
      • Last Sold Price $1,262,000
      • Jul 24, 2024

      Last Listing Agent Michelle Doyle Flow Realty, Inc.

  • /34

    $680,000 Sold Jul 17, 2025

    7 Conant Rd Unit 23, Winchester, MA 01890

    • 2 Beds
    • 2 Baths
    • 1,160 Sq Ft
    • Built 2000

    Last Sold Summary

    • 3% Below List Price
    • $586/SF
    • 18 Days On Market

    Current Estimated Value $687,066

    Last Listing Agent Xin Cui Hooli Homes Boston

    7 Conant Rd Unit 23, Winchester, MA 01890
    • /39

      Est $1,561,851 Not Listed For Sale

      67 Holland St, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 2,452 Sq Ft
      • Built 2005
      67 Holland St, Winchester, MA 01890

      Last Sold Summary

      • 9% Above List Price
      • $583/SF
      • 19 Days On Market
      • Last Sold Price $1,430,000
      • Jan 12, 2024

      Last Listing Agent Kim Covino Compass

  • /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 $1,045,515

    Last Listing Agent Lesley Smith Barrett Sotheby's International Realty

    41 Englewood Rd, Winchester, MA 01890
    • /22

      Est $1,524,778 Not Listed For Sale

      54 Oak St, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 2,708 Sq Ft
      • Built 1895
      54 Oak St, Winchester, MA 01890

      Last Sold Summary

      • 10% Above List Price
      • $510/SF
      • 2 Days On Market
      • Last Sold Price $1,380,000
      • Nov 22, 2023

      Last Listing Agent Mark Donnellan Gibson Sotheby's International Realty

  • /9

    $2,899,000 Sold Jun 27, 2025

    5 Clearwater Rd, Winchester, MA 01890

    • 6 Beds
    • 7.5 Baths
    • 5,658 Sq Ft
    • Built 2025

    Last Sold Summary

    • $512/SF
    • 25 Days On Market

    Current Estimated Value $2,961,350

    Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    5 Clearwater Rd, Winchester, MA 01890
    • /25

      Est $2,273,165 Not Listed For Sale

      48 Oak St, Winchester, MA 01890

      • 5 Beds
      • 4 Baths
      • 4,534 Sq Ft
      • Built 2022
      48 Oak St, Winchester, MA 01890

      Last Sold Summary

      • 6% Above List Price
      • $474/SF
      • 16 Days On Market
      • Last Sold Price $2,150,000
      • Jun 08, 2023

      Last Listing Agent Mark Donnellan Gibson Sotheby's International Realty

  • /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 $375,383

    Last Listing Agent Mark Gilson Keller Williams Realty

    200 Swanton St Unit 432, Winchester, MA 01890
    • /40

      Est $1,277,090 Not Listed For Sale

      58 Nelson St, Winchester, MA 01890

      • 3 Beds
      • 3 Baths
      • 1,835 Sq Ft
      • Built 1870
      58 Nelson St, Winchester, MA 01890

      Last Sold Summary

      • 12% Above List Price
      • $622/SF
      • 5 Days On Market
      • Last Sold Price $1,142,000
      • Aug 21, 2023

      Last Listing Agent Peter Cote Coldwell Banker Realty - Cambridge

  • /30

    $1,330,000 Sold Jun 27, 2025

    17 Mason St, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 1,629 Sq Ft
    • Built 1941

    Last Sold Summary

    • 2% Above List Price
    • $816/SF
    • 5 Days On Market

    Current Estimated Value $1,365,671

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

    17 Mason St, Winchester, MA 01890
    • /27

      Est $1,029,752 Not Listed For Sale

      21 Nelson St, Winchester, MA 01890

      • 3 Beds
      • 1.5 Baths
      • 1,460 Sq Ft
      • Built 1898
      21 Nelson St, Winchester, MA 01890

      Last Sold Summary

      • 8% Above List Price
      • $651/SF
      • 26 Days On Market
      • Last Sold Price $950,000
      • Aug 01, 2024

      Last Listing Agent Ryan Clunan Campion & Company Fine Homes Real Estate

  • /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 $2,177,386

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    4 Winslow Rd, Winchester, MA 01890
    • /37

      Est $1,237,527 Not Listed For Sale

      10 Winchester Place Unit 302, Winchester, MA 01890

      • 2 Beds
      • 2 Baths
      • 2,256 Sq Ft
      • Built 2002
      10 Winchester Place Unit 302, Winchester, MA 01890

      Last Sold Summary

      • 12% Above List Price
      • $490/SF
      • 71 Days On Market
      • Last Sold Price $1,105,000
      • Feb 29, 2024

      Last Listing Agent Kim Covino Compass

  • /38

    $1,627,000 Sold Jul 31, 2025

    32 Oneida Rd, Winchester, MA 01890

    • 5 Beds
    • 4 Baths
    • 2,853 Sq Ft
    • Built 1930

    Last Sold Summary

    • 4% Below List Price
    • $570/SF
    • 7 Days On Market

    Current Estimated Value $1,661,458

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

    32 Oneida Rd, Winchester, MA 01890
    • /25

      Est $1,225,501 Not Listed For Sale

      10 Winchester Place Unit 204, Winchester, MA 01890

      • 2 Beds
      • 2 Baths
      • 2,190 Sq Ft
      • Built 2002
      10 Winchester Place Unit 204, Winchester, MA 01890

      Last Sold Summary

      • 11% Above List Price
      • $502/SF
      • 145 Days On Market
      • Last Sold Price $1,100,000
      • May 15, 2024

      Last Listing Agent Svetlana Sheinia eXp Realty

  • /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 $2,161,677

    Last Listing Agent Dorothea Feffer Churchill Properties

    61 Grove St, Winchester, MA 01890
    • /32

      Est $763,131 Not Listed For Sale

      666 Main St Unit 203, Winchester, MA 01890

      • 2 Beds
      • 2 Baths
      • 1,235 Sq Ft
      • Built 1982
      666 Main St Unit 203, Winchester, MA 01890

      Last Sold Summary

      • $616/SF
      • 10 Days On Market
      • Last Sold Price $761,000
      • Aug 29, 2024

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • /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 $3,420,017

    Last Listing Agent Jay Noble Lamacchia Realty, Inc.

    10 Sheffield W, Winchester, MA 01890
    • /20

      Est $661,421 Not Listed For Sale

      666 Main St Unit L3, Winchester, MA 01890

      • 2 Beds
      • 2 Baths
      • 1,160 Sq Ft
      • Built 1982
      666 Main St Unit L3, Winchester, MA 01890

      Last Sold Summary

      • $569/SF
      • 63 Days On Market
      • Last Sold Price $660,000
      • Feb 12, 2025

      Last Listing Agent Steven Petrello Century 21 North East

  • /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 $1,817,570

    Last Listing Agent Katherine Waters-Clark Compass

    178 Mystic Valley Pkwy, Winchester, MA 01890
    • /37

      Est $2,149,135 Not Listed For Sale

      18 Dix St, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 3,048 Sq Ft
      • Built 1963
      18 Dix St, Winchester, MA 01890

      Last Sold Summary

      • $705/SF
      • 12 Days On Market
      • Last Sold Price $2,150,000
      • Dec 18, 2024

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

  • /42

    $2,950,000 Sold Jun 23, 2025

    51 Wedgemere Ave, Winchester, MA 01890

    • 5 Beds
    • 5 Baths
    • 4,279 Sq Ft
    • Built 1914

    Last Sold Summary

    • 8% Below List Price
    • $689/SF
    • 23 Days On Market

    Current Estimated Value $2,883,725

    Last Listing Agent Kim Covino Compass

    51 Wedgemere Ave, Winchester, MA 01890
    • /35

      Est $1,169,070 Not Listed For Sale

      9 Bacon St, Winchester, MA 01890

      • 5 Beds
      • 1.5 Baths
      • 2,332 Sq Ft
      • Built 1880
      9 Bacon St, Winchester, MA 01890

      Last Sold Summary

      • 2% Below List Price
      • $514/SF
      • 11 Days On Market
      • Last Sold Price $1,199,000
      • Aug 06, 2024

      Last Listing Agent Elena Langlois Compass

  • /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 $1,550,416

    Last Listing Agent Kim Covino Compass

    32 Woodside Rd, Winchester, MA 01890
    • /42

      Est $1,245,895 Not Listed For Sale

      30 Symmes Rd, Winchester, MA 01890

      • 5 Beds
      • 2 Baths
      • 2,341 Sq Ft
      • Built 1910
      30 Symmes Rd, Winchester, MA 01890

      Last Sold Summary

      • 11% Above List Price
      • $478/SF
      • 26 Days On Market
      • Last Sold Price $1,120,000
      • Jul 14, 2023

      Last Listing Agent Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

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