9,208

Winchester, MA Homes

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  • /19

    $3,450,000 Sold Jun 26, 2025

    2 Chestnut St, Winchester, MA 01890

    • 6 Beds
    • 5 Baths
    • 5,500 Sq Ft
    • Built 2025

    Last Sold Summary

    • 4% Below List Price
    • $627/SF
    • 54 Days On Market

    Current Estimated Value $2,904,340

    Last Listing Agent Mark Donnellan Gibson Sotheby's International Realty

    2 Chestnut St, Winchester, MA 01890
    • /42

      Est $1,001,630 Not Listed For Sale

      5 Highland View Ave, Winchester, MA 01890

      • 4 Beds
      • 2 Baths
      • 1,913 Sq Ft
      • Built 1910
      5 Highland View Ave, Winchester, MA 01890

      Last Sold Summary

      • 4% Above List Price
      • $502/SF
      • 4 Days On Market
      • Last Sold Price $960,000
      • Nov 03, 2023

      Last Listing Agent Maryellen Russo The Aland Realty Group LLC

  • /32

    $1,280,000 Sold Jul 15, 2025

    25 Canterbury Rd, Winchester, MA 01890

    • 4 Beds
    • 1.5 Baths
    • 2,349 Sq Ft
    • Built 1948

    Last Sold Summary

    • 20% Above List Price
    • $545/SF
    • 6 Days On Market

    Current Estimated Value $1,359,014

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

    25 Canterbury Rd, Winchester, MA 01890
    • /29

      Est $727,867 Not Listed For Sale

      241 Cross St, Winchester, MA 01890

      • 2 Beds
      • 1 Bath
      • 828 Sq Ft
      • Built 1924
      241 Cross St, Winchester, MA 01890

      Last Sold Summary

      • 10% Above List Price
      • $797/SF
      • 12 Days On Market
      • Last Sold Price $660,000
      • Sep 25, 2023

      Last Listing Agent Paul Cirignano The Synergy Group

  • /42

    $1,890,000 Sold Jun 23, 2025

    15 Kendall St, Winchester, MA 01890

    • 4 Beds
    • 5 Baths
    • 3,148 Sq Ft
    • Built 1993

    Last Sold Summary

    • 2% Above List Price
    • $600/SF
    • 5 Days On Market

    Current Estimated Value $1,840,313

    Last Listing Agent Kim Covino Compass

    15 Kendall St, Winchester, MA 01890
    • /35

      Est $1,792,221 Not Listed For Sale

      12 Pine Grove Park, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 2,623 Sq Ft
      • Built 2024
      12 Pine Grove Park, Winchester, MA 01890

      Last Sold Summary

      • 47% Above List Price
      • $465/SF
      • 14 Days On Market
      • Last Sold Price $1,220,000
      • Oct 11, 2024

      Last Listing Agent Danielle Storella Berkshire Hathaway HomeServices Commonwealth Real Estate

  • /40

    $3,025,000 Sold Jun 13, 2025

    21 Sheffield W, Winchester, MA 01890

    • 6 Beds
    • 5 Baths
    • 5,198 Sq Ft
    • Built 1910

    Last Sold Summary

    • 10% Below List Price
    • $582/SF
    • 50 Days On Market

    Current Estimated Value $3,080,139

    Last Listing Agent Kim Covino Compass

    21 Sheffield W, Winchester, MA 01890
    • /17

      Est $1,165,712 Not Listed For Sale

      269 Cross St Unit 271, Winchester, MA 01890

      • 5 Beds
      • 3 Baths
      • 2,016 Sq Ft
      • Built 1960
      269 Cross St Unit 271, Winchester, MA 01890

      Last Sold Summary

      • 6% Above List Price
      • $546/SF
      • 3 Days On Market
      • Last Sold Price $1,100,000
      • May 16, 2024

      Last Listing Agent Jun Zhang HMW Real Estate, LLC

  • /42

    $1,750,000 Sold Oct 31, 2025

    15 Westland Ave, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,397 Sq Ft
    • Built 1937

    Last Sold Summary

    • $730/SF
    • 1 Day On Market

    Current Estimated Value $1,679,046

    Last Listing Agent Erica Carson Coldwell Banker Realty - Lexington

    15 Westland Ave, Winchester, MA 01890
    • /42

      Est $1,775,174 Not Listed For Sale

      49 Wendell St, Winchester, MA 01890

      • 5 Beds
      • 4.5 Baths
      • 2,944 Sq Ft
      • Built 1942
      49 Wendell St, Winchester, MA 01890

      Last Sold Summary

      • 4% Below List Price
      • $628/SF
      • 4 Days On Market
      • Last Sold Price $1,850,000
      • Nov 12, 2024

      Last Listing Agent Shawn Sullivan RE/MAX

  • /42

    $2,700,000 Sold Aug 18, 2025

    34 Rangeley Rd, Winchester, MA 01890

    • 5 Beds
    • 4.5 Baths
    • 3,708 Sq Ft
    • Built 1929

    Last Sold Summary

    • 8% Above List Price
    • $728/SF
    • 2 Days On Market

    Current Estimated Value $2,655,286

    Last Listing Agent Kim Covino Compass

    34 Rangeley Rd, Winchester, MA 01890
    • /9

      Est $1,643,091 Not Listed For Sale

      118 Wendell St, Winchester, MA 01890

      • 5 Beds
      • 3 Baths
      • 3,415 Sq Ft
      • Built 1955
      118 Wendell St, Winchester, MA 01890

      Last Sold Summary

      • 3% Below List Price
      • $498/SF
      • 7 Days On Market
      • Last Sold Price $1,700,000
      • May 02, 2024

      Last Listing Agent Mark Donnellan Gibson Sotheby's International Realty

  • /42

    $2,000,000 Sold Jan 20, 2026

    5 Wood Ln, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,443 Sq Ft
    • Built 1954

    Last Sold Summary

    • 3% Above List Price
    • $819/SF
    • 12 Days On Market

    Current Estimated Value $2,062,927

    Last Listing Agent Kim Covino Compass

    5 Wood Ln, Winchester, MA 01890
    • /35

      Est $1,270,722 Not Listed For Sale

      14 Hill St, Winchester, MA 01890

      • 4 Beds
      • 1.5 Baths
      • 1,910 Sq Ft
      • Built 1880
      14 Hill St, Winchester, MA 01890

      Last Sold Summary

      • 2% Below List Price
      • $681/SF
      • 5 Days On Market
      • Last Sold Price $1,300,000
      • Jun 18, 2024

      Last Listing Agent Brian and Diana Segool Gibson Sotheby's International Realty

  • /41

    $1,191,000 Sold Jan 13, 2026

    189 High St, Winchester, MA 01890

    • 4 Beds
    • 3 Baths
    • 2,126 Sq Ft
    • Built 1951

    Last Sold Summary

    • 4% Above List Price
    • $560/SF
    • 8 Days On Market

    Current Estimated Value $1,205,544

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

    189 High St, Winchester, MA 01890
    • /29

      Est $1,369,519 Not Listed For Sale

      26 Arthur St, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 2,002 Sq Ft
      • Built 2016
      26 Arthur St, Winchester, MA 01890

      Last Sold Summary

      • 2% Above List Price
      • $668/SF
      • 14 Days On Market
      • Last Sold Price $1,337,500
      • Aug 07, 2024

      Last Listing Agent Anna Mean AC Realty

  • /40

    $1,270,000 Sold May 01, 2026

    11 Ridge St, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 1,888 Sq Ft
    • Built 1956

    Last Sold Summary

    • 6% Above List Price
    • $673/SF
    • 6 Days On Market

    Current Estimated Value $1,308,844

    Last Listing Agent Yvonne Logan Coldwell Banker Realty - Lexington

    11 Ridge St, Winchester, MA 01890
    • /42

      Est $1,382,142 Not Listed For Sale

      18 Forest St, Winchester, MA 01890

      • 3 Beds
      • 2.5 Baths
      • 2,365 Sq Ft
      • Built 2023
      18 Forest St, Winchester, MA 01890

      Last Sold Summary

      • 6% Above List Price
      • $550/SF
      • 15 Days On Market
      • Last Sold Price $1,300,000
      • Oct 30, 2023

      Last Listing Agent Kim Covino Compass

  • /42

    $1,999,000 Sold Dec 12, 2025

    5 Azalea Rd, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 6,232 Sq Ft
    • Built 1980

    Last Sold Summary

    • 6% Below List Price
    • $321/SF
    • 59 Days On Market

    Current Estimated Value $2,024,064

    Last Listing Agent Anthony Marino The Marino Group Collection

    5 Azalea Rd, Winchester, MA 01890
    • /41

      Est $1,118,540 Not Listed For Sale

      28 Garfield Ave, Winchester, MA 01890

      • 4 Beds
      • 1.5 Baths
      • 1,696 Sq Ft
      • Built 1958
      28 Garfield Ave, Winchester, MA 01890

      Last Sold Summary

      • 3% Below List Price
      • $678/SF
      • 7 Days On Market
      • Last Sold Price $1,150,000
      • Jun 03, 2024

      Last Listing Agent Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

  • /42

    $2,500,000 Sold Jul 14, 2025

    17 Harrison St, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 3,719 Sq Ft
    • Built 1952

    Last Sold Summary

    • 11% Above List Price
    • $672/SF
    • 7 Days On Market

    Current Estimated Value $2,440,311

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

    17 Harrison St, Winchester, MA 01890
    • /41

      Est $1,227,653 Not Listed For Sale

      39 Forest St, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 2,302 Sq Ft
      • Built 1900
      39 Forest St, Winchester, MA 01890

      Last Sold Summary

      • 12% Above List Price
      • $478/SF
      • 7 Days On Market
      • Last Sold Price $1,100,000
      • Apr 28, 2023

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

  • /34

    $1,392,500 Sold Jan 09, 2026

    53 Bacon St, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,865 Sq Ft
    • Built 1959

    Last Sold Summary

    • 7% Below List Price
    • $486/SF
    • 37 Days On Market

    Current Estimated Value $1,465,876

    Last Listing Agent Taleen Chiofaro Leading Edge Real Estate

    53 Bacon St, Winchester, MA 01890
    • /38

      Est $1,935,242 Not Listed For Sale

      25 Marion St, Winchester, MA 01890

      • 5 Beds
      • 5 Baths
      • 4,234 Sq Ft
      • Built 1900
      25 Marion St, Winchester, MA 01890

      Last Sold Summary

      • 3% Above List Price
      • $443/SF
      • 5 Days On Market
      • Last Sold Price $1,875,000
      • Aug 06, 2024

      Last Listing Agent Anne Spry Barrett Sotheby's International Realty

  • /41

    $790,001 Sold Aug 15, 2025

    9 Emerson Ct, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 1,441 Sq Ft
    • Built 1901

    Last Sold Summary

    • 1% Below List Price
    • $548/SF
    • 12 Days On Market

    Current Estimated Value $842,227

    Last Listing Agent Rodrigo Serrano Leading Edge Real Estate

    9 Emerson Ct, Winchester, MA 01890
    • /33

      Est $1,137,027 Not Listed For Sale

      17 Cross St, Winchester, MA 01890

      • 4 Beds
      • 1.5 Baths
      • 2,490 Sq Ft
      • Built 1927
      17 Cross St, Winchester, MA 01890

      Last Sold Summary

      • 2% Below List Price
      • $466/SF
      • 2 Days On Market
      • Last Sold Price $1,160,000
      • Jul 12, 2024

      Last Listing Agent Kim Covino Compass

  • /37

    $2,200,000 Sold Jul 09, 2025

    20 Elm St, Winchester, MA 01890

    • 6 Beds
    • 3.5 Baths
    • 3,901 Sq Ft
    • Built 2011

    Last Sold Summary

    • 13% Above List Price
    • $564/SF
    • 4 Days On Market

    Current Estimated Value $2,171,893

    Last Listing Agent Kim Covino Compass

    20 Elm St, Winchester, MA 01890
    • /38

      Est $1,324,455 Not Listed For Sale

      39 Nathaniel Rd, Winchester, MA 01890

      • 3 Beds
      • 1.5 Baths
      • 2,799 Sq Ft
      • Built 1950
      39 Nathaniel Rd, Winchester, MA 01890

      Last Sold Summary

      • 10% Above List Price
      • $429/SF
      • 26 Days On Market
      • Last Sold Price $1,200,000
      • Jan 09, 2024

      Last Listing Agent Michaela Mahtani Leading Edge Real Estate

  • /41

    $3,900,000 Sold Oct 24, 2025

    12 Ledgewood Rd, Winchester, MA 01890

    • 5 Beds
    • 4.5 Baths
    • 5,069 Sq Ft
    • Built 2016

    Last Sold Summary

    • 1% Above List Price
    • $769/SF
    • 2 Days On Market

    Current Estimated Value $3,792,141

    Last Listing Agent Leigh Ventura Compass

    12 Ledgewood Rd, Winchester, MA 01890
    • /38

      Est $1,229,103 Not Listed For Sale

      6 Nathaniel Rd, Winchester, MA 01890

      • 4 Beds
      • 2 Baths
      • 2,217 Sq Ft
      • Built 1960
      6 Nathaniel Rd, Winchester, MA 01890

      Last Sold Summary

      • 7% Above List Price
      • $519/SF
      • 5 Days On Market
      • Last Sold Price $1,150,000
      • Jul 26, 2024

      Last Listing Agent Kim Covino Compass

  • /33

    $1,600,000 Sold Oct 10, 2025

    10 Olde Lyme Rd, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 3,478 Sq Ft
    • Built 1960

    Last Sold Summary

    • 18% Below List Price
    • $460/SF
    • 57 Days On Market

    Current Estimated Value $1,640,759

    Last Listing Agent Darryl Brian RE/MAX Bentley's

    10 Olde Lyme Rd, Winchester, MA 01890
    • /42

      Not Listed For Sale

      15 Tufts Rd, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 2,634 Sq Ft
      • Built 2023
      15 Tufts Rd, Winchester, MA 01890

      Last Sold Summary

      • $543/SF
      • 9 Days On Market
      • Last Sold Price $1,430,000
      • Sep 01, 2023

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • /25

    $955,225 Sold Jan 27, 2026

    41 Squire Rd, Winchester, MA 01890

    • 4 Beds
    • 1.5 Baths
    • 2,162 Sq Ft
    • Built 1958

    Last Sold Summary

    • 3% Below List Price
    • $442/SF
    • 33 Days On Market

    Current Estimated Value $1,010,741

    Last Listing Agent William Cordts Coldwell Banker Realty - Waltham

    41 Squire Rd, Winchester, MA 01890
    • /39

      Est $1,323,447 Not Listed For Sale

      37 Tufts Rd, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 1,969 Sq Ft
      • Built 1950
      37 Tufts Rd, Winchester, MA 01890

      Last Sold Summary

      • 9% Below List Price
      • $736/SF
      • 6 Days On Market
      • Last Sold Price $1,450,000
      • Dec 26, 2024

      Last Listing Agent Amanda Armstrong Compass

  • /26

    $340,000 Sold Feb 02, 2026

    200 Swanton St Unit 630, Winchester, MA 01890

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

    Last Sold Summary

    • 1% Below List Price
    • $555/SF
    • 15 Days On Market

    Current Estimated Value $340,686

    Last Listing Agent Angela Hirtle Lyv Realty

    200 Swanton St Unit 630, Winchester, MA 01890
    • /24

      Est $1,169,608 Not Listed For Sale

      32 Tufts Rd, Winchester, MA 01890

      • 3 Beds
      • 1.5 Baths
      • 2,139 Sq Ft
      • Built 1950
      32 Tufts Rd, Winchester, MA 01890

      Last Sold Summary

      • 12% Above List Price
      • $486/SF
      • 4 Days On Market
      • Last Sold Price $1,040,000
      • Oct 30, 2023

      Last Listing Agent Rose Hall Blue Ocean Realty, LLC

  • /40

    $2,450,000 Sold Jan 09, 2026

    29 Shepard Ct, Winchester, MA 01890

    • 6 Beds
    • 5 Baths
    • 4,594 Sq Ft
    • Built 2025

    Last Sold Summary

    • 2% Above List Price
    • $533/SF
    • 6 Days On Market

    Current Estimated Value $2,370,191

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

    29 Shepard Ct, Winchester, MA 01890
    • /34

      Est $1,067,459 Not Listed For Sale

      5 Bates Rd, Winchester, MA 01890

      • 5 Beds
      • 2 Baths
      • 1,918 Sq Ft
      • Built 1959
      5 Bates Rd, Winchester, MA 01890

      Last Sold Summary

      • 25% Above List Price
      • $444/SF
      • 6 Days On Market
      • Last Sold Price $852,000
      • Nov 10, 2023

      Last Listing Agent Stephanie Johnson Premium Realty Group LLC

  • /40

    $1,850,000 Sold Mar 26, 2026

    20 Grove Place, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 3,294 Sq Ft
    • Built 1910

    Last Sold Summary

    • 1% Below List Price
    • $562/SF
    • 40 Days On Market

    Current Estimated Value $1,867,931

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    20 Grove Place, Winchester, MA 01890
    • /34

      Est $1,108,791 Not Listed For Sale

      30 Irving St Unit 32, Winchester, MA 01890

      • 4 Beds
      • 2 Baths
      • 2,477 Sq Ft
      • Built 1930
      30 Irving St Unit 32, Winchester, MA 01890

      Last Sold Summary

      • 7% Above List Price
      • $419/SF
      • 5 Days On Market
      • Last Sold Price $1,039,000
      • Dec 22, 2023

      Last Listing Agent Sylvia Shen Keller Williams Realty Leading Edge

Showing Results 481 - 520, Page 13 of 18

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