9,208

Winchester, MA Homes

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  • /41

    $1,400,000 Sold Mar 06, 2026

    26 Berkshire Dr, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,316 Sq Ft
    • Built 1970

    Last Sold Summary

    • 5% Below List Price
    • $604/SF
    • 77 Days On Market

    Current Estimated Value $1,409,989

    Last Listing Agent DANIEL BEIRNE OpenDoor Brokerage LLC

    26 Berkshire Dr, Winchester, MA 01890
    • /37

      Est $1,329,800 Not Listed For Sale

      5 Sylvester Ct, Winchester, MA 01890

      • 4 Beds
      • 2 Baths
      • 2,280 Sq Ft
      • Built 1963
      5 Sylvester Ct, Winchester, MA 01890

      Last Sold Summary

      • 8% Below List Price
      • $636/SF
      • 6 Days On Market
      • Last Sold Price $1,450,000
      • Jul 25, 2024

      Last Listing Agent Philip Vita Compass

  • /39

    $2,200,000 Sold Jul 14, 2025

    4 Fairfield Place, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 3,896 Sq Ft
    • Built 2016

    Last Sold Summary

    • 4% Below List Price
    • $565/SF
    • 11 Days On Market

    Current Estimated Value $2,227,887

    Last Listing Agent Kim Covino Compass

    4 Fairfield Place, Winchester, MA 01890
    • /25

      Not Listed For Sale

      48 Water St Unit 50, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 2,632 Sq Ft
      • Built 1911
      48 Water St Unit 50, Winchester, MA 01890

      Last Sold Summary

      • 60% Above List Price
      • $551/SF
      • 3 Days On Market
      • Last Sold Price $1,450,000
      • Feb 10, 2025

      Last Listing Agent Chris Kostopoulos Keller Williams Realty

  • /40

    $770,000 Sold May 05, 2026

    171 Swanton St Unit 21, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 1,834 Sq Ft
    • Built 1985

    Last Sold Summary

    • 3% Above List Price
    • $420/SF
    • 5 Days On Market

    Current Estimated Value $836,799

    Last Listing Agent Jesse Mason Colby Hunter Realty

    171 Swanton St Unit 21, Winchester, MA 01890
    • /28

      Est $683,646 Not Listed For Sale

      7 Conant Rd Unit 27, Winchester, MA 01890

      • 2 Beds
      • 2 Baths
      • 1,160 Sq Ft
      • Built 2000
      7 Conant Rd Unit 27, Winchester, MA 01890

      Last Sold Summary

      • 4% Below List Price
      • $616/SF
      • 7 Days On Market
      • Last Sold Price $715,000
      • Jul 18, 2024

      Last Listing Agent Alyssa Vozzella Cameron Real Estate Group

  • /32

    $740,000 Sold Sep 09, 2025

    15 Governors Ave Unit 1, Winchester, MA 01890

    • 3 Beds
    • 1 Bath
    • 1,358 Sq Ft
    • Built 1903

    Last Sold Summary

    • 7% Above List Price
    • $545/SF
    • 8 Days On Market

    Current Estimated Value $724,692

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

    15 Governors Ave Unit 1, Winchester, MA 01890
    • /42

      Est $691,106 Not Listed For Sale

      7 Conant Rd Unit 24, Winchester, MA 01890

      • 2 Beds
      • 2 Baths
      • 1,196 Sq Ft
      • Built 2000
      7 Conant Rd Unit 24, Winchester, MA 01890

      Last Sold Summary

      • 1% Above List Price
      • $570/SF
      • 68 Days On Market
      • Last Sold Price $682,000
      • Mar 28, 2025

      Last Listing Agent Paul Bettencourt Beaudoin & Associates, REALTOR®

  • /41

    $1,500,000 Sold Jun 30, 2025

    23 Elmwood Ave Unit C, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,189 Sq Ft
    • Built 2017

    Last Sold Summary

    • $685/SF
    • 1 Day On Market

    Current Estimated Value $1,490,880

    Last Listing Agent Kim Covino Compass

    23 Elmwood Ave Unit C, Winchester, MA 01890
    • /41

      Est $738,440 Not Listed For Sale

      7 Conant Rd Unit 45, Winchester, MA 01890

      • 2 Beds
      • 2.5 Baths
      • 1,510 Sq Ft
      • Built 1999
      7 Conant Rd Unit 45, Winchester, MA 01890

      Last Sold Summary

      • 3% Below List Price
      • $503/SF
      • 6 Days On Market
      • Last Sold Price $760,000
      • Sep 18, 2023

      Last Listing Agent Nicole Brodeur Keller Williams Realty-Merrimack

  • /41

    $1,200,000 Sold Nov 21, 2025

    415-417 Washington St, Winchester, MA 01890

    • 5 Beds
    • 2 Baths
    • 2,610 Sq Ft
    • Built 1907

    Last Sold Summary

    • 4% Above List Price
    • $460/SF
    • 10 Days On Market

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

    415-417 Washington St, Winchester, MA 01890
    • /19

      Est $712,619 Not Listed For Sale

      7 Conant Rd Unit 41, Winchester, MA 01890

      • 2 Beds
      • 2.5 Baths
      • 1,421 Sq Ft
      • Built 1999
      7 Conant Rd Unit 41, Winchester, MA 01890

      Last Sold Summary

      • 3% Below List Price
      • $515/SF
      • 19 Days On Market
      • Last Sold Price $732,500
      • Jun 11, 2024

      Last Listing Agent The Diamond Group Keller Williams Realty-Merrimack

  • /33

    $1,650,000 Sold Jun 06, 2025

    34 Coolidge Rd, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 3,338 Sq Ft
    • Built 1980

    Last Sold Summary

    • 3% Above List Price
    • $494/SF
    • 7 Days On Market

    Current Estimated Value $1,717,734

    Last Listing Agent Pauline Marino Coldwell Banker Realty - Lexington

    34 Coolidge Rd, Winchester, MA 01890
    • /15

      Est $745,910 Not Listed For Sale

      7 Conant Rd Unit 66, Winchester, MA 01890

      • 2 Beds
      • 2.5 Baths
      • 1,605 Sq Ft
      • Built 1999
      7 Conant Rd Unit 66, Winchester, MA 01890

      Last Sold Summary

      • 2% Below List Price
      • $476/SF
      • 5 Days On Market
      • Last Sold Price $764,000
      • Jul 31, 2023

      Last Listing Agent Ida Bianco Coldwell Banker Realty - Lexington

  • /42

    $397,000 Sold Nov 14, 2025

    200 Swanton St Unit T11, Winchester, MA 01890

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

    Last Sold Summary

    • 3% Below List Price
    • $626/SF
    • 31 Days On Market

    Current Estimated Value $391,363

    Last Listing Agent Shannon Jenkins RE/MAX Realty Experts

    200 Swanton St Unit T11, Winchester, MA 01890
    • /20

      Est $705,016 Not Listed For Sale

      7 Conant Rd Unit 52, Winchester, MA 01890

      • 2 Beds
      • 2 Baths
      • 1,532 Sq Ft
      • Built 1999
      7 Conant Rd Unit 52, Winchester, MA 01890

      Last Sold Summary

      • 1% Above List Price
      • $457/SF
      • 5 Days On Market
      • Last Sold Price $700,000
      • Aug 09, 2024

      Last Listing Agent Judith Moore Barrett Sotheby's International Realty

  • /39

    $1,425,000 Sold Jun 25, 2025

    9 Thornberry Rd, Winchester, MA 01890

    • 4 Beds
    • 3 Baths
    • 2,496 Sq Ft
    • Built 1957

    Last Sold Summary

    • 8% Above List Price
    • $571/SF
    • 6 Days On Market

    Current Estimated Value $1,406,088

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

    9 Thornberry Rd, Winchester, MA 01890
    • /29

      Est $822,434 Not Listed For Sale

      7 Conant Rd Unit 16, Winchester, MA 01890

      • 3 Beds
      • 2.5 Baths
      • 1,482 Sq Ft
      • Built 1997
      7 Conant Rd Unit 16, Winchester, MA 01890

      Last Sold Summary

      • 3% Below List Price
      • $574/SF
      • 30 Days On Market
      • Last Sold Price $850,000
      • Aug 18, 2023

      Last Listing Agent William Natoli Compass

  • /26

    $1,140,000 Sold Jun 03, 2025

    7 Indian Hill Rd, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 1,646 Sq Ft
    • Built 1955

    Last Sold Summary

    • 1% Below List Price
    • $693/SF
    • 8 Days On Market

    Current Estimated Value $1,266,590

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

    7 Indian Hill Rd, Winchester, MA 01890
    • /33

      Est $732,545 Not Listed For Sale

      7 Conant Rd Unit 15, Winchester, MA 01890

      • 2 Beds
      • 2.5 Baths
      • 1,512 Sq Ft
      • Built 1997
      7 Conant Rd Unit 15, Winchester, MA 01890

      Last Sold Summary

      • 6% Above List Price
      • $456/SF
      • 6 Days On Market
      • Last Sold Price $690,000
      • Nov 03, 2023

      Last Listing Agent Dream Team Dreamega International Realty LLC

  • /25

    $1,226,000 Sold Jul 15, 2025

    8 Ware Rd, Winchester, MA 01890

    • 3 Beds
    • 3 Baths
    • 2,534 Sq Ft
    • Built 1980

    Last Sold Summary

    • 17% Above List Price
    • $484/SF
    • 6 Days On Market

    Current Estimated Value $1,285,155

    Last Listing Agent Alex Navarro Coldwell Banker Realty - Beverly

    8 Ware Rd, Winchester, MA 01890
    • /33

      Est $1,519,714 Not Listed For Sale

      41 White St Unit 43, Winchester, MA 01890

      • 4 Beds
      • 4 Baths
      • 2,442 Sq Ft
      • Built 2016
      41 White St Unit 43, Winchester, MA 01890

      Last Sold Summary

      • 3% Above List Price
      • $606/SF
      • 7 Days On Market
      • Last Sold Price $1,480,000
      • Jun 18, 2024

      Last Listing Agent Sharon Tang U3 Realty, LLC

  • /31

    $1,050,000 Sold Oct 22, 2025

    36 Elmwood Ave Unit 4, Winchester, MA 01890

    • 2 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 2021

    Last Sold Summary

    • $810/SF
    • 9 Days On Market

    Current Estimated Value $1,056,255

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

    36 Elmwood Ave Unit 4, Winchester, MA 01890
    • /30

      Est $807,738 Not Listed For Sale

      171 Swanton St Unit 63, Winchester, MA 01890

      • 2 Beds
      • 2.5 Baths
      • 1,823 Sq Ft
      • Built 1985
      171 Swanton St Unit 63, Winchester, MA 01890

      Last Sold Summary

      • 7% Above List Price
      • $415/SF
      • 5 Days On Market
      • Last Sold Price $757,000
      • May 24, 2024

      Last Listing Agent Gary Vrotsos Coldwell Banker Realty - Cambridge

  • /24

    $945,000 Sold Feb 12, 2026

    139 High St, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 1,302 Sq Ft
    • Built 1949

    Last Sold Summary

    • 5% Below List Price
    • $726/SF
    • 61 Days On Market

    Current Estimated Value $978,831

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

    139 High St, Winchester, MA 01890
    • /31

      Est $825,102 Not Listed For Sale

      171 Swanton St Unit 61, Winchester, MA 01890

      • 3 Beds
      • 1.5 Baths
      • 1,836 Sq Ft
      • Built 1985
      171 Swanton St Unit 61, Winchester, MA 01890

      Last Sold Summary

      • 7% Above List Price
      • $418/SF
      • 24 Days On Market
      • Last Sold Price $768,000
      • Jun 21, 2023

      Last Listing Agent Nancy McLaughlin Redfin Corp.

  • /41

    $2,630,000 Sold Dec 08, 2025

    10 Sheffield Rd, Winchester, MA 01890

    • 7 Beds
    • 5.5 Baths
    • 5,864 Sq Ft
    • Built 1916

    Last Sold Summary

    • 9% Below List Price
    • $448/SF
    • 141 Days On Market

    Current Estimated Value $2,688,005

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    10 Sheffield Rd, Winchester, MA 01890
    • /22

      Est $745,956 Not Listed For Sale

      171 Swanton St Unit 49, Winchester, MA 01890

      • 2 Beds
      • 1.5 Baths
      • 1,435 Sq Ft
      • Built 1985
      171 Swanton St Unit 49, Winchester, MA 01890

      Last Sold Summary

      • 7% Above List Price
      • $488/SF
      • 7 Days On Market
      • Last Sold Price $700,000
      • Jun 22, 2023

      Last Listing Agent Paul Cirignano The Synergy Group

  • /2

    $1,430,000 Sold Jul 10, 2025

    189 Mystic Valley Pkwy, Winchester, MA 01890

    • 6 Beds
    • 2.5 Baths
    • 3,543 Sq Ft
    • Built 1850

    Last Sold Summary

    • 25% Below List Price
    • $404/SF
    • 106 Days On Market

    Current Estimated Value $1,613,343

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    189 Mystic Valley Pkwy, Winchester, MA 01890
    • /41

      Est $750,857 Not Listed For Sale

      171 Swanton St Unit 33, Winchester, MA 01890

      • 2 Beds
      • 1.5 Baths
      • 1,475 Sq Ft
      • Built 1985
      171 Swanton St Unit 33, Winchester, MA 01890

      Last Sold Summary

      • 2% Above List Price
      • $498/SF
      • 8 Days On Market
      • Last Sold Price $735,000
      • Oct 11, 2024

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • /31

    $380,000 Sold May 23, 2025

    200 Swanton St Unit 722, Winchester, MA 01890

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

    Last Sold Summary

    • 1% Below List Price
    • $620/SF
    • 15 Days On Market

    Current Estimated Value $380,013

    Last Listing Agent Yang Liu Weston Realty LLC

    200 Swanton St Unit 722, Winchester, MA 01890
    • /24

      Est $790,360 Not Listed For Sale

      171 Swanton St Unit 27, Winchester, MA 01890

      • 2 Beds
      • 2.5 Baths
      • 1,435 Sq Ft
      • Built 1985
      171 Swanton St Unit 27, Winchester, MA 01890

      Last Sold Summary

      • 12% Above List Price
      • $490/SF
      • 4 Days On Market
      • Last Sold Price $703,000
      • Oct 25, 2023

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

  • /16

    $825,000 Sold Aug 29, 2025

    171 Swanton St Unit 64, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 1,825 Sq Ft
    • Built 1985

    Last Sold Summary

    • 4% Below List Price
    • $452/SF
    • 5 Days On Market

    Current Estimated Value $838,967

    Last Listing Agent Xiaoli Xie JKS Boston Realty LLC

    171 Swanton St Unit 64, Winchester, MA 01890
    • /27

      Est $772,712 Not Listed For Sale

      171 Swanton St Unit 17, Winchester, MA 01890

      • 2 Beds
      • 2.5 Baths
      • 1,430 Sq Ft
      • Built 1984
      171 Swanton St Unit 17, Winchester, MA 01890

      Last Sold Summary

      • 10% Above List Price
      • $490/SF
      • 4 Days On Market
      • Last Sold Price $700,000
      • Apr 28, 2023

      Last Listing Agent Susan Flynn The Delamere Flynn Group, LLC

  • /41

    $2,380,000 Sold Feb 25, 2026

    8 Buckman Dr, Winchester, MA 01890

    • 5 Beds
    • 5.5 Baths
    • 4,773 Sq Ft
    • Built 1970

    Last Sold Summary

    • 4% Above List Price
    • $499/SF
    • 4 Days On Market

    Current Estimated Value $2,354,716

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    8 Buckman Dr, Winchester, MA 01890
    • /37

      Est $753,383 Not Listed For Sale

      171 Swanton St Unit 16, Winchester, MA 01890

      • 2 Beds
      • 2.5 Baths
      • 1,430 Sq Ft
      • Built 1984
      171 Swanton St Unit 16, Winchester, MA 01890

      Last Sold Summary

      • 3% Below List Price
      • $541/SF
      • 13 Days On Market
      • Last Sold Price $773,000
      • Dec 16, 2024

      Last Listing Agent Wei Wang WW Real Estate LLC

  • /38

    $2,600,000 Sold May 19, 2025

    3 Lagrange St, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 4,060 Sq Ft
    • Built 1912

    Last Sold Summary

    • 5% Below List Price
    • $640/SF
    • 88 Days On Market

    Current Estimated Value $2,404,930

    Last Listing Agent Mark Donnellan Gibson Sotheby's International Realty

    3 Lagrange St, Winchester, MA 01890
    • /33

      Est $1,392,013 Not Listed For Sale

      85 Loring Ave, Winchester, MA 01890

      • 3 Beds
      • 2.5 Baths
      • 2,340 Sq Ft
      • Built 1962
      85 Loring Ave, Winchester, MA 01890

      Last Sold Summary

      • 11% Above List Price
      • $534/SF
      • 5 Days On Market
      • Last Sold Price $1,250,000
      • Mar 15, 2024

      Last Listing Agent Sheila McDougall Leading Edge Real Estate

  • /42

    $1,775,000 Sold Aug 15, 2025

    19 Pilgrim Dr, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 3,150 Sq Ft
    • Built 1961

    Last Sold Summary

    • $563/SF
    • 6 Days On Market

    Current Estimated Value $1,809,077

    Last Listing Agent Gorfinkle Group eXp Realty

    19 Pilgrim Dr, Winchester, MA 01890
    • /36

      Est $1,467,946 Not Listed For Sale

      99 Loring Ave, Winchester, MA 01890

      • 4 Beds
      • 4 Baths
      • 2,019 Sq Ft
      • Built 1985
      99 Loring Ave, Winchester, MA 01890

      Last Sold Summary

      • 6% Above List Price
      • $684/SF
      • 4 Days On Market
      • Last Sold Price $1,380,000
      • Aug 02, 2023

      Last Listing Agent Moshe Elmekias Gibson Sothebys International Realty

Showing Results 441 - 480, Page 12 of 18

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