283

Recently Sold Winchester, MA Homes

Section Image
  • /38

    $1,062,350 Sold Aug 22, 2025

    8 Garfield Ave, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft
    • Built 1940

    Last Sold Summary

    • 11% Below List Price
    • $692/SF
    • 42 Days On Market

    Current Estimated Value $1,067,455

    Last Listing Agent Kim Covino Compass

    8 Garfield Ave, Winchester, MA 01890
  • /34

    $2,000,000 Sold Jun 02, 2025

    11 Chesterford Rd E, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 3,039 Sq Ft
    • Built 1927

    Last Sold Summary

    • 9% Below List Price
    • $658/SF
    • 7 Days On Market

    Current Estimated Value $2,018,088

    Last Listing Agent Joseph Pollack Redfin Corp.

    11 Chesterford Rd E, Winchester, MA 01890
  • /29

    $1,150,000 Sold Dec 12, 2025

    50 Lincoln St, Winchester, MA 01890

    • 4 Beds
    • 1.5 Baths
    • 2,004 Sq Ft
    • Built 1919

    Last Sold Summary

    • 8% Below List Price
    • $574/SF
    • 20 Days On Market

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

    50 Lincoln St, Winchester, MA 01890
  • /37

    $1,200,000 Sold Sep 25, 2025

    147 Highland Ave, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 1,884 Sq Ft
    • Built 1919

    Last Sold Summary

    • 14% Below List Price
    • $637/SF
    • 103 Days On Market

    Last Listing Agent Kim Covino Compass

    147 Highland Ave, Winchester, MA 01890
  • /42

    $1,678,500 Sold Sep 25, 2025

    10 Blossom Hill Rd, Winchester, MA 01890

    • 4 Beds
    • 2 Baths
    • 3,838 Sq Ft
    • Built 1951

    Last Sold Summary

    • 1% Below List Price
    • $437/SF
    • 10 Days On Market

    Last Listing Agent Stephen DeConto Cameron Real Estate Group

    10 Blossom Hill Rd, Winchester, MA 01890
  • /33

    $1,325,000 Sold Dec 22, 2025

    12 Canterbury Rd, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 1,942 Sq Ft
    • Built 1942

    Last Sold Summary

    • 10% Above List Price
    • $682/SF
    • 9 Days On Market

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

    12 Canterbury Rd, Winchester, MA 01890
  • /42

    $1,725,000 Sold Sep 19, 2025

    9 Pilgrim Dr, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,541 Sq Ft
    • Built 1960

    Last Sold Summary

    • 8% Above List Price
    • $679/SF
    • 6 Days On Market

    Current Estimated Value $1,697,360

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

    9 Pilgrim Dr, Winchester, MA 01890
  • /32

    $1,115,000 Sold Jul 15, 2025

    48 Winford Way, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 1,978 Sq Ft
    • Built 1951

    Last Sold Summary

    • 7% Below List Price
    • $564/SF
    • 9 Days On Market

    Current Estimated Value $1,150,757

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

    48 Winford Way, Winchester, MA 01890
  • /33

    $1,280,000 Sold Oct 03, 2025

    162 Forest St, Winchester, MA 01890

    • 4 Beds
    • 1.5 Baths
    • 1,900 Sq Ft
    • Built 1930

    Last Sold Summary

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

    Last Listing Agent Paul Cirignano The Synergy Group

    162 Forest St, Winchester, MA 01890
  • /34

    $2,450,000 Sold Jun 24, 2025

    31 Lawson Rd, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 5,218 Sq Ft
    • Built 1999

    Last Sold Summary

    • 2% Below List Price
    • $470/SF
    • 19 Days On Market

    Current Estimated Value $2,557,126

    Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    31 Lawson Rd, Winchester, MA 01890
  • /26

    $2,160,000 Sold Jul 14, 2025

    19 Sussex Rd, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 4,023 Sq Ft
    • Built 1998

    Last Sold Summary

    • 4% Below List Price
    • $537/SF
    • 37 Days On Market

    Current Estimated Value $2,190,676

    Last Listing Agent Ida Bianco Coldwell Banker Realty - Lexington

    19 Sussex Rd, Winchester, MA 01890
  • /32

    $1,280,000 Sold Jul 16, 2025

    18 Hemingway St, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 2,137 Sq Ft
    • Built 2015

    Last Sold Summary

    • 6% Below List Price
    • $599/SF
    • 21 Days On Market

    Current Estimated Value $1,290,709

    Last Listing Agent Julia Xie Keller Williams Realty-Merrimack

    18 Hemingway St, Winchester, MA 01890
  • /42

    $1,656,000 Sold Oct 31, 2025

    4 Aricia Ln, Winchester, MA 01890

    • 4 Beds
    • 5 Baths
    • 5,361 Sq Ft
    • Built 1984

    Last Sold Summary

    • 13% Below List Price
    • $309/SF
    • 88 Days On Market

    Last Listing Agent The McLaren D'Agostino Team Compass

    4 Aricia Ln, Winchester, MA 01890
  • /32

    $999,999 Sold Nov 21, 2025

    16 Park Ave Unit 2, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 1,756 Sq Ft
    • Built 1915

    Last Sold Summary

    • 5% Above List Price
    • $569/SF
    • 9 Days On Market

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

    16 Park Ave Unit 2, Winchester, MA 01890
  • /41

    $1,150,000 Sold Nov 14, 2025

    89 Main St, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,648 Sq Ft
    • Built 1932

    Last Sold Summary

    • 2% Above List Price
    • $434/SF
    • 8 Days On Market

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    89 Main St, Winchester, MA 01890
  • /33

    $1,240,000 Sold Aug 20, 2025

    3 Socrates Way, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,570 Sq Ft
    • Built 1966

    Last Sold Summary

    • 5% Below List Price
    • $482/SF
    • 9 Days On Market

    Current Estimated Value $1,289,261

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

    3 Socrates Way, Winchester, MA 01890
  • /16

    $650,000 Sold Jun 23, 2025

    27 Elm St, Winchester, MA 01890

    • 2 Beds
    • 1.5 Baths
    • 1,007 Sq Ft
    • Built 1900

    Last Sold Summary

    • 30% Above List Price
    • $645/SF
    • 7 Days On Market

    Current Estimated Value $706,560

    Last Listing Agent Shao Realty Group REMAX Executive Realty

    27 Elm St, Winchester, MA 01890
  • /42

    $1,330,000 Sold Aug 21, 2025

    14 Hillside Ave, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,605 Sq Ft
    • Built 1870

    Last Sold Summary

    • 19% Below List Price
    • $511/SF
    • 73 Days On Market

    Current Estimated Value $1,413,879

    Last Listing Agent Seeme Moreira Coldwell Banker Realty - Lexington

    14 Hillside Ave, Winchester, MA 01890
  • /11

    $1,269,000 Sold Jun 04, 2025

    158 Swanton St Unit 160, Winchester, MA 01890

    • 3 Beds
    • 3.5 Baths
    • 2,136 Sq Ft
    • Built 2025

    Last Sold Summary

    • $594/SF
    • 1 Day On Market

    Current Estimated Value $1,476,500

    Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    158 Swanton St Unit 160, Winchester, MA 01890
  • /38

    $940,000 Sold Dec 23, 2025

    446 Highland Ave, Winchester, MA 01890

    • 2 Beds
    • 1.5 Baths
    • 2,033 Sq Ft
    • Built 1926

    Last Sold Summary

    • 6% Below List Price
    • $462/SF
    • 14 Days On Market

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    446 Highland Ave, Winchester, MA 01890
  • /39

    $3,599,000 Sold Nov 20, 2025

    5 Stratford Rd, Winchester, MA 01890

    • 6 Beds
    • 4.5 Baths
    • 5,876 Sq Ft
    • Built 1870

    Last Sold Summary

    • $612/SF
    • 27 Days On Market

    Last Listing Agent Kim Covino Compass

    5 Stratford Rd, Winchester, MA 01890
  • /42

    $1,187,000 Sold Jun 18, 2025

    44 Forest St, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 1,906 Sq Ft
    • Built 1926

    Last Sold Summary

    • 1% Below List Price
    • $623/SF
    • 12 Days On Market

    Current Estimated Value $1,180,127

    Last Listing Agent Kim Covino Compass

    44 Forest St, Winchester, MA 01890
  • /42

    $2,862,500 Sold Oct 10, 2025

    54 Wedgemere Ave, Winchester, MA 01890

    • 6 Beds
    • 3.5 Baths
    • 5,238 Sq Ft
    • Built 1915

    Last Sold Summary

    • 4% Below List Price
    • $546/SF
    • 6 Days On Market

    Last Listing Agent Kim Covino Compass

    54 Wedgemere Ave, Winchester, MA 01890
  • /39

    $1,400,000 Sold Jul 14, 2025

    20 Fletcher St Unit 20, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,282 Sq Ft
    • Built 2025

    Last Sold Summary

    • 3% Below List Price
    • $613/SF
    • 38 Days On Market

    Last Listing Agent Kim Covino Compass

    20 Fletcher St Unit 20, Winchester, MA 01890
  • /38

    $1,924,000 Sold Jul 10, 2025

    5 Hastings Rd, Winchester, MA 01890

    • 4 Beds
    • 4 Baths
    • 4,195 Sq Ft
    • Built 1995

    Last Sold Summary

    • 1% Above List Price
    • $459/SF
    • 4 Days On Market

    Current Estimated Value $1,974,469

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    5 Hastings Rd, Winchester, MA 01890
  • /21

    $425,000 Sold Jan 03, 2025

    64 Highland Ave Unit 18, Winchester, MA 01890

    • 1 Bed
    • 1 Bath
    • 758 Sq Ft
    • Built 1982

    Last Sold Summary

    • $561/SF
    • 9 Days On Market

    Current Estimated Value $435,057

    Last Listing Agent Diane Plunkett Plunkett Properties

    64 Highland Ave Unit 18, Winchester, MA 01890
  • /30

    $1,185,000 Sold Oct 08, 2025

    5 Emerson Ct, Winchester, MA 01890

    • 3 Beds
    • 3.5 Baths
    • 2,000 Sq Ft
    • Built 1870

    Last Sold Summary

    • 1% Below List Price
    • $592/SF
    • 5 Days On Market

    Last Listing Agent Elaine Song Coldwell Banker Realty - Lexington

    5 Emerson Ct, Winchester, MA 01890
  • /36

    $1,250,000 Sold Nov 14, 2025

    35 Harvard St, Winchester, MA 01890

    • 5 Beds
    • 2 Baths
    • 1,706 Sq Ft
    • Built 1880

    Last Sold Summary

    • 4% Below List Price
    • $733/SF
    • 17 Days On Market

    Last Listing Agent Joanne Mulkerin J. Mulkerin Realty

    35 Harvard St, Winchester, MA 01890
  • /31

    $1,355,000 Sold Nov 20, 2025

    4 Sargent Rd, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,865 Sq Ft
    • Built 1945

    Last Sold Summary

    • 3% Below List Price
    • $473/SF
    • 10 Days On Market

    Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    4 Sargent Rd, Winchester, MA 01890
  • /36

    $749,900 Sold Jun 13, 2025

    7 Conant Rd Unit 34, Winchester, MA 01890

    • 2 Beds
    • 2 Baths
    • 1,545 Sq Ft
    • Built 1999

    Last Sold Summary

    • $485/SF
    • 8 Days On Market

    Current Estimated Value $746,675

    Last Listing Agent Melanie Lentini Leading Edge Real Estate

    7 Conant Rd Unit 34, Winchester, MA 01890
  • /39

    $1,450,000 Sold Dec 26, 2024

    37 Tufts Rd, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 1,969 Sq Ft
    • Built 1950

    Last Sold Summary

    • 16% Above List Price
    • $736/SF
    • 6 Days On Market

    Current Estimated Value $1,397,499

    Last Listing Agent Amanda Armstrong Compass

    37 Tufts Rd, Winchester, MA 01890
  • /36

    $1,950,000 Sold Sep 25, 2025

    4 Fieldstone Dr, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 4,378 Sq Ft
    • Built 1987

    Last Sold Summary

    • 11% Below List Price
    • $445/SF
    • 40 Days On Market

    Last Listing Agent Wenli Zheng Fairview Partners International LLC

    4 Fieldstone Dr, Winchester, MA 01890
  • /33

    $642,000 Sold Jan 28, 2025

    20 Hancock St, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 1,752 Sq Ft
    • Built 1880

    Last Sold Summary

    • 8% Below List Price
    • $366/SF
    • 56 Days On Market

    Current Estimated Value $697,944

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

    20 Hancock St, Winchester, MA 01890
  • /42

    $2,799,000 Sold Jan 30, 2025

    16 Ardley Place, Winchester, MA 01890

    • 5 Beds
    • 6 Baths
    • 4,324 Sq Ft
    • Built 1938

    Last Sold Summary

    • $647/SF
    • 68 Days On Market

    Current Estimated Value $2,708,044

    Last Listing Agent Ann Norberg Coldwell Banker Realty - Lexington

    16 Ardley Place, Winchester, MA 01890
  • /25

    $1,450,000 Sold Feb 10, 2025

    48 Water St Unit 50, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 2,632 Sq Ft
    • Built 1911

    Last Sold Summary

    • $551/SF
    • 3 Days On Market

    Current Estimated Value $2,319,000

    Last Listing Agent Chris Kostopoulos Keller Williams Realty

    48 Water St Unit 50, Winchester, MA 01890
  • /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 $2,206,226

    Last Listing Agent Kim Covino Compass

    4 Fairfield Place, Winchester, MA 01890
  • /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 $728,327

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

    15 Governors Ave Unit 1, Winchester, MA 01890
  • /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 $1,492,812

    Last Listing Agent Kim Covino Compass

    23 Elmwood Ave Unit C, Winchester, MA 01890
  • /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
  • /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 $1,678,989

    Last Listing Agent Pauline Marino Coldwell Banker Realty - Lexington

    34 Coolidge Rd, Winchester, MA 01890

Showing Results 121 - 160, Page 4 of 8

How to Buy a Home How to Finance a Home How to Sell a Home