9,206

Winchester, MA Homes

Section Image
  • 70 Grove St, Winchester, MA 01890
    70 Grove St, Winchester, MA 01890
    70 Grove St, Winchester, MA 01890
    /25

    $1,160,000

    Sold Jul 30, 2026

    70 Grove St, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 1,996 Sq Ft
    • Built 1949

    Last Sold Summary

    • 16% Above List Price
    • $581/SF
    • 6 Days On Market

    Current Estimated Value $1,049,921

    Last Listing Agent Maija Sawyer Puleo William Raveis R.E. & Home Services

    70 Grove St, Winchester, MA 01890
    • 7 Conant Rd Unit 41, Winchester, MA 01890
      7 Conant Rd Unit 41, Winchester, MA 01890
      7 Conant Rd Unit 41, Winchester, MA 01890
      /19

      Est $721,871

      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

      • 19 Days On Market

      Last Listing Agent The Diamond Group Keller Williams Realty-Merrimack

  • 78 Bacon St, Winchester, MA 01890
    78 Bacon St, Winchester, MA 01890
    78 Bacon St, Winchester, MA 01890
    /42

    $2,300,000

    Sold Aug 28, 2026

    78 Bacon St, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 5,230 Sq Ft
    • Built 1910

    Last Sold Summary

    • 12% Below List Price
    • $440/SF
    • 67 Days On Market

    Current Estimated Value $2,511,404

    Last Listing Agent Kim Covino Compass

    78 Bacon St, Winchester, MA 01890
    • 7 Conant Rd Unit 37, Winchester, MA 01890
      7 Conant Rd Unit 37, Winchester, MA 01890
      7 Conant Rd Unit 37, Winchester, MA 01890
      /25

      Est $718,291

      Not Listed For Sale

      7 Conant Rd Unit 37, Winchester, MA 01890

      • 2 Beds
      • 2.5 Baths
      • 1,539 Sq Ft
      • Built 1999
      7 Conant Rd Unit 37, Winchester, MA 01890

      Last Sold Summary

      • 33 Days On Market

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

  • 415-417 Washington St, Winchester, MA 01890
    415-417 Washington St, Winchester, MA 01890
    415-417 Washington St, 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
    • 7 Conant Rd Unit 34, Winchester, MA 01890
      7 Conant Rd Unit 34, Winchester, MA 01890
      7 Conant Rd Unit 34, Winchester, MA 01890
      /36

      Est $728,190

      Not Listed For Sale

      7 Conant Rd Unit 34, Winchester, MA 01890

      • 2 Beds
      • 2 Baths
      • 1,545 Sq Ft
      • Built 1999
      7 Conant Rd Unit 34, Winchester, MA 01890

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Melanie Lentini Leading Edge Real Estate

  • 200 Swanton St Unit T11, Winchester, MA 01890
    200 Swanton St Unit T11, Winchester, MA 01890
    200 Swanton St Unit T11, Winchester, MA 01890
    /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 $398,277

    Last Listing Agent Shannon Jenkins RE/MAX Realty Experts

    200 Swanton St Unit T11, Winchester, MA 01890
    • 7 Conant Rd Unit 60, Winchester, MA 01890
      7 Conant Rd Unit 60, Winchester, MA 01890
      7 Conant Rd Unit 60, Winchester, MA 01890
      /19

      Est $724,541

      Not Listed For Sale

      7 Conant Rd Unit 60, Winchester, MA 01890

      • 2 Beds
      • 2.5 Baths
      • 1,634 Sq Ft
      • Built 1999
      7 Conant Rd Unit 60, Winchester, MA 01890

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Irene Novia Loka Matahari Real Estate LLC

  • 15 East St, Winchester, MA 01890
    15 East St, Winchester, MA 01890
    15 East St, Winchester, MA 01890
    /39

    $1,060,000

    Sold May 28, 2026

    15 East St, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 1,973 Sq Ft
    • Built 1976

    Last Sold Summary

    • 12% Below List Price
    • $537/SF
    • 37 Days On Market

    Current Estimated Value $1,062,373

    Last Listing Agent Kim Covino Compass

    15 East St, Winchester, MA 01890
    • 7 Conant Rd Unit 52, Winchester, MA 01890
      7 Conant Rd Unit 52, Winchester, MA 01890
      7 Conant Rd Unit 52, Winchester, MA 01890
      /20

      Est $717,480

      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

      • 5 Days On Market

      Last Listing Agent Judith Moore Barrett Sotheby's International Realty

  • 29 Ginn Rd, Winchester, MA 01890
    29 Ginn Rd, Winchester, MA 01890
    29 Ginn Rd, Winchester, MA 01890
    /39

    $3,799,000

    Sold Sep 02, 2026

    29 Ginn Rd, Winchester, MA 01890

    • 6 Beds
    • 7.5 Baths
    • 6,000 Sq Ft
    • Built 2026

    Last Sold Summary

    • $633/SF
    • 17 Days On Market

    Current Estimated Value $3,166,093

    Last Listing Agent Peter Kasseris Serhant

    29 Ginn Rd, Winchester, MA 01890
    • 7 Conant Rd Unit 15, Winchester, MA 01890
      7 Conant Rd Unit 15, Winchester, MA 01890
      7 Conant Rd Unit 15, Winchester, MA 01890
      /33

      Est $715,207

      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 Days On Market

      Last Listing Agent Dream Team Dreamega International Realty LLC

  • 63 Dunster Ln, Winchester, MA 01890
    63 Dunster Ln, Winchester, MA 01890
    63 Dunster Ln, Winchester, MA 01890
    /9

    $825,000

    Sold Jul 31, 2026

    63 Dunster Ln, Winchester, MA 01890

    • 2 Beds
    • 1 Bath
    • 1,208 Sq Ft
    • Built 1910

    Last Sold Summary

    • 2% Above List Price
    • $683/SF
    • 9 Days On Market

    Current Estimated Value $817,464

    Last Listing Agent john ferolito Keller Williams Realty

    63 Dunster Ln, Winchester, MA 01890
    • 41 White St Unit 43, Winchester, MA 01890
      41 White St Unit 43, Winchester, MA 01890
      41 White St Unit 43, Winchester, MA 01890
      /33

      Est $1,498,247

      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

      • 7 Days On Market

      Last Listing Agent Sharon Tang U3 Realty, LLC

  • 36 Elmwood Ave Unit 4, Winchester, MA 01890
    36 Elmwood Ave Unit 4, Winchester, MA 01890
    36 Elmwood Ave Unit 4, Winchester, MA 01890
    /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 $1,074,904

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

    36 Elmwood Ave Unit 4, Winchester, MA 01890
    • 171 Swanton St Unit 64, Winchester, MA 01890
      171 Swanton St Unit 64, Winchester, MA 01890
      171 Swanton St Unit 64, Winchester, MA 01890
      /16

      Est $847,544

      Not Listed For Sale

      171 Swanton St Unit 64, Winchester, MA 01890

      • 3 Beds
      • 2.5 Baths
      • 1,825 Sq Ft
      • Built 1985
      171 Swanton St Unit 64, Winchester, MA 01890

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Xiaoli Xie JKS Boston Realty LLC

  • 139 High St, Winchester, MA 01890
    139 High St, Winchester, MA 01890
    139 High St, Winchester, MA 01890
    /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 $1,043,516

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

    139 High St, Winchester, MA 01890
    • 171 Swanton St Unit 63, Winchester, MA 01890
      171 Swanton St Unit 63, Winchester, MA 01890
      171 Swanton St Unit 63, Winchester, MA 01890
      /30

      Est $793,527

      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

      • 5 Days On Market

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

  • 10 Sheffield Rd, Winchester, MA 01890
    10 Sheffield Rd, Winchester, MA 01890
    10 Sheffield Rd, Winchester, MA 01890
    /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 $3,080,565

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    10 Sheffield Rd, Winchester, MA 01890
    • 171 Swanton St Unit 33, Winchester, MA 01890
      171 Swanton St Unit 33, Winchester, MA 01890
      171 Swanton St Unit 33, Winchester, MA 01890
      /41

      Est $749,286

      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

      • 8 Days On Market

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • 2 George Rd Unit 2, Winchester, MA 01890
    2 George Rd Unit 2, Winchester, MA 01890
    2 George Rd Unit 2, Winchester, MA 01890
    /26

    $680,000

    Sold Jul 10, 2026

    2 George Rd Unit 2, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Built 1962

    Last Sold Summary

    • 5% Above List Price
    • $523/SF
    • 6 Days On Market

    Current Estimated Value $661,625

    Last Listing Agent Kim Covino Compass

    2 George Rd Unit 2, Winchester, MA 01890
    • 171 Swanton St Unit 27, Winchester, MA 01890
      171 Swanton St Unit 27, Winchester, MA 01890
      171 Swanton St Unit 27, Winchester, MA 01890
      /24

      Est $776,871

      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

      • 4 Days On Market

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

  • 8 Buckman Dr, Winchester, MA 01890
    8 Buckman Dr, Winchester, MA 01890
    8 Buckman Dr, Winchester, MA 01890
    /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 $2,357,812

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    8 Buckman Dr, Winchester, MA 01890
    • 171 Swanton St Unit 16, Winchester, MA 01890
      171 Swanton St Unit 16, Winchester, MA 01890
      171 Swanton St Unit 16, Winchester, MA 01890
      /37

      Est $771,433

      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

      • 13 Days On Market

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

  • 49 Sheridan Cir, Winchester, MA 01890
    49 Sheridan Cir, Winchester, MA 01890
    49 Sheridan Cir, Winchester, MA 01890
    /3

    $2,409,000

    Sold Jul 10, 2026

    49 Sheridan Cir, Winchester, MA 01890

    • 5 Beds
    • 4.5 Baths
    • 5,881 Sq Ft
    • Built 2014

    Last Sold Summary

    • $410/SF
    • 2 Days On Market

    Current Estimated Value $2,399,540

    Last Listing Agent Kim Covino Compass

    49 Sheridan Cir, Winchester, MA 01890
    • 171 Swanton St Unit 12, Winchester, MA 01890
      171 Swanton St Unit 12, Winchester, MA 01890
      171 Swanton St Unit 12, Winchester, MA 01890
      /28

      Est $797,572

      Not Listed For Sale

      171 Swanton St Unit 12, Winchester, MA 01890

      • 2 Beds
      • 2.5 Baths
      • 1,435 Sq Ft
      • Built 1984
      171 Swanton St Unit 12, Winchester, MA 01890

      Last Sold Summary

      • 8 Days On Market

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

  • 15 Westland Ave, Winchester, MA 01890
    15 Westland Ave, Winchester, MA 01890
    15 Westland Ave, Winchester, MA 01890
    /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 $1,694,830

    Last Listing Agent Erica Carson Coldwell Banker Realty - Lexington

    15 Westland Ave, Winchester, MA 01890
    • 85 Loring Ave, Winchester, MA 01890
      85 Loring Ave, Winchester, MA 01890
      85 Loring Ave, Winchester, MA 01890
      /33

      Est $1,309,059

      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

      • 5 Days On Market

      Last Listing Agent Sheila McDougall Leading Edge Real Estate

  • 5 Wood Ln, Winchester, MA 01890
    5 Wood Ln, Winchester, MA 01890
    5 Wood Ln, Winchester, MA 01890
    /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 $1,976,355

    Last Listing Agent Kim Covino Compass

    5 Wood Ln, Winchester, MA 01890
    • 5 Highland View Ave, Winchester, MA 01890
      5 Highland View Ave, Winchester, MA 01890
      5 Highland View Ave, Winchester, MA 01890
      /42

      Est $1,056,488

      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 Days On Market

      Last Listing Agent Maryellen Russo The Aland Realty Group LLC

  • 46 Clark St, Winchester, MA 01890
    46 Clark St, Winchester, MA 01890
    46 Clark St, Winchester, MA 01890
    /36

    $1,035,000

    Sold Sep 18, 2026

    46 Clark St, Winchester, MA 01890

    • 4 Beds
    • 1.5 Baths
    • 1,777 Sq Ft
    • Built 1921

    Last Sold Summary

    • 6% Below List Price
    • $582/SF
    • 36 Days On Market

    Current Estimated Value $1,040,666

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    46 Clark St, Winchester, MA 01890
    • 235 Cross St, Winchester, MA 01890
      235 Cross St, Winchester, MA 01890
      235 Cross St, Winchester, MA 01890
      /32

      Est $941,026

      Not Listed For Sale

      235 Cross St, Winchester, MA 01890

      • 3 Beds
      • 1.5 Baths
      • 1,931 Sq Ft
      • Built 1956
      235 Cross St, Winchester, MA 01890

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Melanie Lentini Leading Edge Real Estate

  • 189 High St, Winchester, MA 01890
    189 High St, Winchester, MA 01890
    189 High St, Winchester, MA 01890
    /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 $1,257,771

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

    189 High St, Winchester, MA 01890
    • 241 Cross St, Winchester, MA 01890
      241 Cross St, Winchester, MA 01890
      241 Cross St, Winchester, MA 01890
      /29

      Est $701,061

      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 Days On Market

      Last Listing Agent Paul Cirignano The Synergy Group

  • 11 Ridge St, Winchester, MA 01890
    11 Ridge St, Winchester, MA 01890
    11 Ridge St, Winchester, MA 01890
    /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 $1,235,860

    Last Listing Agent Yvonne Logan Coldwell Banker Realty - Lexington

    11 Ridge St, Winchester, MA 01890
    • 18 Pine Grove Park, Winchester, MA 01890
      18 Pine Grove Park, Winchester, MA 01890
      18 Pine Grove Park, Winchester, MA 01890
      /27

      Est $1,034,165

      Not Listed For Sale

      18 Pine Grove Park, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 2,873 Sq Ft
      • Built 1958
      18 Pine Grove Park, Winchester, MA 01890

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Michele Forester EXIT Premier Real Estate

  • 5 Azalea Rd, Winchester, MA 01890
    5 Azalea Rd, Winchester, MA 01890
    5 Azalea Rd, Winchester, MA 01890
    /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 $2,098,075

    Last Listing Agent Anthony Marino The Marino Group Collection

    5 Azalea Rd, Winchester, MA 01890
    • 12 Pine Grove Park, Winchester, MA 01890
      12 Pine Grove Park, Winchester, MA 01890
      12 Pine Grove Park, Winchester, MA 01890
      /35

      Est $1,779,057

      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

      • 14 Days On Market

      Last Listing Agent Danielle Storella Berkshire Hathaway HomeServices Commonwealth Real Estate

  • 76 Woodside Rd, Winchester, MA 01890
    76 Woodside Rd, Winchester, MA 01890
    76 Woodside Rd, Winchester, MA 01890
    /25

    $1,080,000

    Sold May 12, 2026

    76 Woodside Rd, Winchester, MA 01890

    • 4 Beds
    • 2 Baths
    • 1,552 Sq Ft
    • Built 1920

    Last Sold Summary

    • 8% Above List Price
    • $696/SF
    • 5 Days On Market

    Current Estimated Value $1,088,550

    Last Listing Agent Michael Pierce Mystic Properties Real Estate

    76 Woodside Rd, Winchester, MA 01890
    • 269 Cross St Unit 271, Winchester, MA 01890
      269 Cross St Unit 271, Winchester, MA 01890
      269 Cross St Unit 271, Winchester, MA 01890
      /17

      Est $1,154,725

      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

      • 3 Days On Market

      Last Listing Agent Jun Zhang HMW Real Estate, LLC

Showing Results 481 - 520, Page 13 of 18

Massachusetts Middlesex County

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