9,220

Winchester, MA Homes

Section Image
  • /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 $2,689,756

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    10 Sheffield Rd, Winchester, MA 01890
    • /29

      Est $826,856 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

      Last Listing Agent William Natoli Compass

  • /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 $1,581,923

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    189 Mystic Valley Pkwy, Winchester, MA 01890
    • /33

      Est $745,032 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

      • 8% Above List Price
      • $456/SF
      • 6 Days On Market

      Last Sold Price $690,000

      Last Listing Agent Dream Team Dreamega International Realty LLC

  • /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 $382,219

    Last Listing Agent Yang Liu Weston Realty LLC

    200 Swanton St Unit 722, Winchester, MA 01890
    • /33

      Est $1,534,211 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

      • 4% Above List Price
      • $606/SF
      • 7 Days On Market

      Last Sold Price $1,480,000

      Last Listing Agent Sharon Tang U3 Realty, 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 $827,947

    Last Listing Agent Xiaoli Xie JKS Boston Realty LLC

    171 Swanton St Unit 64, Winchester, MA 01890
    • /30

      Est $837,987 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

      • 11% Above List Price
      • $415/SF
      • 5 Days On Market

      Last Sold Price $757,000

      Last Listing Agent Gary Vrotsos Coldwell Banker Realty - Cambridge

  • /42

    $1,815,000 Sold Apr 15, 2025

    29 Allen Rd, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,810 Sq Ft
    • Built 1935

    Last Sold Summary

    • 14% Above List Price
    • $646/SF
    • 8 Days On Market

    Current Estimated Value $1,761,423

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

    29 Allen Rd, Winchester, MA 01890
    • /31

      Est $871,224 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

      • 13% Above List Price
      • $418/SF
      • 24 Days On Market

      Last Sold Price $768,000

      Last Listing Agent Nancy McLaughlin Redfin Corp.

  • /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 $2,278,620

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    8 Buckman Dr, Winchester, MA 01890
    • /22

      Est $767,187 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

      • 10% Above List Price
      • $488/SF
      • 7 Days On Market

      Last Sold Price $700,000

      Last Listing Agent Paul Cirignano The Synergy Group

  • /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 $2,360,540

    Last Listing Agent Mark Donnellan Gibson Sotheby's International Realty

    3 Lagrange St, Winchester, MA 01890
    • /41

      Est $761,396 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

      • 4% Above List Price
      • $498/SF
      • 8 Days On Market

      Last Sold Price $735,000

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • /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 $1,766,098

    Last Listing Agent Gorfinkle Group eXp Realty

    19 Pilgrim Dr, Winchester, MA 01890
    • /24

      Est $778,676 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

      • 11% Above List Price
      • $490/SF
      • 4 Days On Market

      Last Sold Price $703,000

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

  • /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 $2,833,708

    Last Listing Agent Mark Donnellan Gibson Sotheby's International Realty

    2 Chestnut St, Winchester, MA 01890
    • /27

      Est $783,354 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

      • 12% Above List Price
      • $490/SF
      • 4 Days On Market

      Last Sold Price $700,000

      Last Listing Agent Susan Flynn The Delamere Flynn 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 $1,333,513

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

    25 Canterbury Rd, Winchester, MA 01890
    • /37

      Est $785,405 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

      • 2% Above List Price
      • $541/SF
      • 13 Days On Market

      Last Sold Price $773,000

      Last Listing Agent Wei Wang WW Real Estate LLC

  • /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 $1,790,300

    Last Listing Agent Kim Covino Compass

    15 Kendall St, Winchester, MA 01890
    • /33

      Est $1,384,975 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

      Last Listing Agent Sheila McDougall Leading Edge 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 $3,037,729

    Last Listing Agent Kim Covino Compass

    21 Sheffield W, Winchester, MA 01890
    • /36

      Est $1,433,197 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

      • 4% Above List Price
      • $684/SF
      • 4 Days On Market

      Last Sold Price $1,380,000

      Last Listing Agent Moshe Elmekias Gibson Sothebys International Realty

  • /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 $1,682,516

    Last Listing Agent Erica Carson Coldwell Banker Realty - Lexington

    15 Westland Ave, Winchester, MA 01890
    • /42

      Est $1,039,946 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

      • 8% Above List Price
      • $502/SF
      • 4 Days On Market

      Last Sold Price $960,000

      Last Listing Agent Maryellen Russo The Aland Realty Group LLC

  • /39

    $3,199,000 Sold May 09, 2025

    12 Prospect St, Winchester, MA 01890

    • 7 Beds
    • 5 Baths
    • 6,694 Sq Ft
    • Built 1880

    Last Sold Summary

    • $478/SF
    • 9 Days On Market

    Current Estimated Value $3,104,002

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    12 Prospect St, Winchester, MA 01890
    • /29

      Est $742,206 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

      • 12% Above List Price
      • $797/SF
      • 12 Days On Market

      Last Sold Price $660,000

      Last Listing Agent Paul Cirignano The Synergy Group

  • /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 $2,578,026

    Last Listing Agent Kim Covino Compass

    34 Rangeley Rd, Winchester, MA 01890
    • /35

      Est $1,760,878 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

      • 44% Above List Price
      • $465/SF
      • 14 Days On Market

      Last Sold Price $1,220,000

      Last Listing Agent Danielle Storella Berkshire Hathaway HomeServices Commonwealth Real Estate

  • /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 $1,950,247

    Last Listing Agent Kim Covino Compass

    5 Wood Ln, Winchester, MA 01890
    • /17

      Est $1,125,074 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

      • 2% Above List Price
      • $546/SF
      • 3 Days On Market

      Last Sold Price $1,100,000

      Last Listing Agent Jun Zhang HMW Real Estate, LLC

  • /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
    • /42

      Est $1,824,373 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

      • 1% Below List Price
      • $628/SF
      • 4 Days On Market

      Last Sold Price $1,850,000

      Last Listing Agent Shawn Sullivan RE/MAX

  • /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 $2,004,657

    Last Listing Agent Anthony Marino The Marino Group Collection

    5 Azalea Rd, Winchester, MA 01890
    • /9

      Est $1,713,196 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

      • 1% Above List Price
      • $498/SF
      • 7 Days On Market

      Last Sold Price $1,700,000

      Last Listing Agent Mark Donnellan Gibson Sotheby's International Realty

  • /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
    • /35

      Est $1,303,813 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

      • $681/SF
      • 5 Days On Market

      Last Sold Price $1,300,000

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

  • /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
    • /29

      Est $1,384,019 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

      • 3% Above List Price
      • $668/SF
      • 14 Days On Market

      Last Sold Price $1,337,500

      Last Listing Agent Anna Mean AC Realty

Showing Results 441 - 480, Page 12 of 18

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