9,209

Winchester, MA Homes

Section Image
  • 322 Cambridge St, Winchester, MA 01890
    322 Cambridge St, Winchester, MA 01890
    322 Cambridge St, Winchester, MA 01890
    /15

    $1,088,000 Sold May 08, 2025

    322 Cambridge St, Winchester, MA 01890

    • 4 Beds
    • 2 Baths
    • 2,172 Sq Ft
    • Built 1985

    Last Sold Summary

    • 18% Above List Price
    • $501/SF
    • 6 Days On Market

    Current Estimated Value $1,104,121

    Last Listing Agent Joanne McDonnell RE/MAX Real Estate Center

    322 Cambridge St, Winchester, MA 01890
    • 11 Stratford Rd, Winchester, MA 01890
      11 Stratford Rd, Winchester, MA 01890
      11 Stratford Rd, Winchester, MA 01890
      /31

      Est $2,041,187 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,529 Sq Ft

      11 Stratford Rd, Winchester, MA 01890

      11 Stratford Rd, Winchester, MA 01890
  • 112 Wendell St, Winchester, MA 01890
    112 Wendell St, Winchester, MA 01890
    112 Wendell St, Winchester, MA 01890
    /41

    $1,335,000 Sold Feb 04, 2026

    112 Wendell St, Winchester, MA 01890

    • 4 Beds
    • 3 Baths
    • 2,854 Sq Ft
    • Built 1952

    Last Sold Summary

    • 4% Below List Price
    • $468/SF
    • 9 Days On Market

    Last Listing Agent Steve McKenna Gibson Sotheby's International Realty

    112 Wendell St, Winchester, MA 01890
    • 19 Everett Ave, Winchester, MA 01890
      19 Everett Ave, Winchester, MA 01890
      19 Everett Ave, Winchester, MA 01890
      /40

      Est $2,566,645 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 3,938 Sq Ft

      19 Everett Ave, Winchester, MA 01890

      19 Everett Ave, Winchester, MA 01890
  • 382 S Border Rd, Winchester, MA 01890
    382 S Border Rd, Winchester, MA 01890
    382 S Border Rd, Winchester, MA 01890
    /42

    $2,450,000 Sold Nov 17, 2025

    382 S Border Rd, Winchester, MA 01890

    • 6 Beds
    • 5.5 Baths
    • 4,563 Sq Ft
    • Built 2025

    Last Sold Summary

    • 9% Below List Price
    • $537/SF
    • 8 Days On Market

    Last Listing Agent Lucille Murray Gibson Sotheby's International Realty

    382 S Border Rd, Winchester, MA 01890
    • 33 Everett Ave, Winchester, MA 01890
      33 Everett Ave, Winchester, MA 01890
      33 Everett Ave, Winchester, MA 01890
      /42

      Est $3,709,688 Not Listed For Sale

      • 6 Beds
      • 5.5 Baths
      • 6,600 Sq Ft

      33 Everett Ave, Winchester, MA 01890

      33 Everett Ave, Winchester, MA 01890
  • 19 Yale St, Winchester, MA 01890
    19 Yale St, Winchester, MA 01890
    19 Yale St, Winchester, MA 01890
    /42

    $2,350,000 Sold Jun 16, 2025

    19 Yale St, Winchester, MA 01890

    • 6 Beds
    • 3.5 Baths
    • 4,212 Sq Ft
    • Built 1880

    Last Sold Summary

    • 6% Below List Price
    • $558/SF
    • 15 Days On Market

    Current Estimated Value $2,416,365

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    19 Yale St, Winchester, MA 01890
    • 39 Everett Ave, Winchester, MA 01890
      39 Everett Ave, Winchester, MA 01890
      39 Everett Ave, Winchester, MA 01890
      /34

      Est $3,131,052 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 4,860 Sq Ft

      39 Everett Ave, Winchester, MA 01890

      39 Everett Ave, Winchester, MA 01890
  • 8 Garfield Ave, Winchester, MA 01890
    8 Garfield Ave, Winchester, MA 01890
    8 Garfield Ave, Winchester, MA 01890
    /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 $1,067,025

    Last Listing Agent Kim Covino Compass

    8 Garfield Ave, Winchester, MA 01890
    • 48 Everett Ave, Winchester, MA 01890
      48 Everett Ave, Winchester, MA 01890
      48 Everett Ave, Winchester, MA 01890
      /42

      Est $4,793,659 Not Listed For Sale

      • 7 Beds
      • 6.5 Baths
      • 9,075 Sq Ft

      48 Everett Ave, Winchester, MA 01890

      48 Everett Ave, Winchester, MA 01890
  • 11 Chesterford Rd E, Winchester, MA 01890
    11 Chesterford Rd E, Winchester, MA 01890
    11 Chesterford Rd E, 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 $2,030,370

    Last Listing Agent Joseph Pollack Redfin Corp.

    11 Chesterford Rd E, Winchester, MA 01890
    • 32 Everett Ave, Winchester, MA 01890
      32 Everett Ave, Winchester, MA 01890
      32 Everett Ave, Winchester, MA 01890
      /42

      Est $5,330,706 Not Listed For Sale

      • 7 Beds
      • 6 Baths
      • 9,835 Sq Ft

      32 Everett Ave, Winchester, MA 01890

      32 Everett Ave, Winchester, MA 01890
  • 50 Lincoln St, Winchester, MA 01890
    50 Lincoln St, Winchester, MA 01890
    50 Lincoln St, 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
    • 10 Wyman Ct, Winchester, MA 01890
      10 Wyman Ct, Winchester, MA 01890
      10 Wyman Ct, Winchester, MA 01890
      /24

      Est $757,117 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,432 Sq Ft

      10 Wyman Ct, Winchester, MA 01890

      10 Wyman Ct, Winchester, MA 01890
  • 147 Highland Ave, Winchester, MA 01890
    147 Highland Ave, Winchester, MA 01890
    147 Highland Ave, 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

    Current Estimated Value $1,293,806

    Last Listing Agent Kim Covino Compass

    147 Highland Ave, Winchester, MA 01890
    • 83 Church St Unit 14, Winchester, MA 01890
      83 Church St Unit 14, Winchester, MA 01890
      83 Church St Unit 14, Winchester, MA 01890
      /42

      Est $932,227 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,317 Sq Ft

      83 Church St Unit 14, Winchester, MA 01890

      83 Church St Unit 14, Winchester, MA 01890
  • 10 Blossom Hill Rd, Winchester, MA 01890
    10 Blossom Hill Rd, Winchester, MA 01890
    10 Blossom Hill Rd, 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

    Current Estimated Value $1,724,601

    Last Listing Agent Stephen DeConto Cameron Real Estate Group

    10 Blossom Hill Rd, Winchester, MA 01890
    • 83 Church St Unit 6, Winchester, MA 01890
      83 Church St Unit 6, Winchester, MA 01890
      83 Church St Unit 6, Winchester, MA 01890
      /32

      Est $980,267 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,493 Sq Ft

      83 Church St Unit 6, Winchester, MA 01890

      83 Church St Unit 6, Winchester, MA 01890
  • 12 Canterbury Rd, Winchester, MA 01890
    12 Canterbury Rd, Winchester, MA 01890
    12 Canterbury 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
    • 60 Church St, Winchester, MA 01890
      60 Church St, Winchester, MA 01890
      60 Church St, Winchester, MA 01890
      /24

      Est $1,642,947 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,572 Sq Ft

      60 Church St, Winchester, MA 01890

      60 Church St, Winchester, MA 01890
  • 9 Pilgrim Dr, Winchester, MA 01890
    9 Pilgrim Dr, Winchester, MA 01890
    9 Pilgrim Dr, 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
    • 3 Ravine Rd, Winchester, MA 01890
      3 Ravine Rd, Winchester, MA 01890
      3 Ravine Rd, Winchester, MA 01890
      /42

      Est $3,945,819 Not Listed For Sale

      • 6 Beds
      • 6.5 Baths
      • 8,178 Sq Ft

      3 Ravine Rd, Winchester, MA 01890

      3 Ravine Rd, Winchester, MA 01890
  • 48 Winford Way, Winchester, MA 01890
    48 Winford Way, Winchester, MA 01890
    48 Winford Way, 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 $1,157,589

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

    48 Winford Way, Winchester, MA 01890
    • 82 Church St Unit 84, Winchester, MA 01890
      82 Church St Unit 84, Winchester, MA 01890
      82 Church St Unit 84, Winchester, MA 01890
      /38

      Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 2,465 Sq Ft

      82 Church St Unit 84, Winchester, MA 01890

      82 Church St Unit 84, Winchester, MA 01890
  • 162 Forest St, Winchester, MA 01890
    162 Forest St, Winchester, MA 01890
    162 Forest St, 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

    Current Estimated Value $1,293,634

    Last Listing Agent Paul Cirignano The Synergy Group

    162 Forest St, Winchester, MA 01890
    • 12 Norwood St, Winchester, MA 01890
      12 Norwood St, Winchester, MA 01890
      12 Norwood St, Winchester, MA 01890
      /42

      Est $2,364,089 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,979 Sq Ft

      12 Norwood St, Winchester, MA 01890

      12 Norwood St, Winchester, MA 01890
  • 31 Lawson Rd, Winchester, MA 01890
    31 Lawson Rd, Winchester, MA 01890
    31 Lawson Rd, 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 $2,606,005

    Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    31 Lawson Rd, Winchester, MA 01890
    • 6 Harrington Rd, Winchester, MA 01890
      6 Harrington Rd, Winchester, MA 01890
      6 Harrington Rd, Winchester, MA 01890
      /36

      Est $2,029,819 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,688 Sq Ft

      6 Harrington Rd, Winchester, MA 01890

      6 Harrington Rd, Winchester, MA 01890
  • 19 Sussex Rd, Winchester, MA 01890
    19 Sussex Rd, Winchester, MA 01890
    19 Sussex 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 $2,168,297

    Last Listing Agent Ida Bianco Coldwell Banker Realty - Lexington

    19 Sussex Rd, Winchester, MA 01890
    • 73 Bacon St, Winchester, MA 01890
      73 Bacon St, Winchester, MA 01890
      73 Bacon St, Winchester, MA 01890
      /35

      Est $2,542,654 Not Listed For Sale

      • 6 Beds
      • 3.5 Baths
      • 4,453 Sq Ft

      73 Bacon St, Winchester, MA 01890

      73 Bacon St, Winchester, MA 01890
  • 18 Hemingway St, Winchester, MA 01890
    18 Hemingway St, Winchester, MA 01890
    18 Hemingway St, 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 $1,294,121

    Last Listing Agent Julia Xie Keller Williams Realty-Merrimack

    18 Hemingway St, Winchester, MA 01890
    • 59 Bacon St, Winchester, MA 01890
      59 Bacon St, Winchester, MA 01890
      59 Bacon St, Winchester, MA 01890
      /35

      Est $3,298,130 Not Listed For Sale

      • 5 Beds
      • 5.5 Baths
      • 5,981 Sq Ft

      59 Bacon St, Winchester, MA 01890

      59 Bacon St, Winchester, MA 01890
  • 4 Aricia Ln, Winchester, MA 01890
    4 Aricia Ln, Winchester, MA 01890
    4 Aricia Ln, 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

    Current Estimated Value $1,699,988

    Last Listing Agent The McLaren D'Agostino Team Compass

    4 Aricia Ln, Winchester, MA 01890
    • 4 Rangeley Rd Unit 4A, Winchester, MA 01890
      4 Rangeley Rd Unit 4A, Winchester, MA 01890
      4 Rangeley Rd Unit 4A, Winchester, MA 01890
      /42

      Est $1,393,752 Not Listed For Sale

      • 6 Beds
      • 3.5 Baths
      • 3,647 Sq Ft

      4 Rangeley Rd Unit 4A, Winchester, MA 01890

      4 Rangeley Rd Unit 4A, Winchester, MA 01890
  • 16 Park Ave Unit 2, Winchester, MA 01890
    16 Park Ave Unit 2, Winchester, MA 01890
    16 Park Ave Unit 2, 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
    • 2 Fairfield Place, Winchester, MA 01890
      2 Fairfield Place, Winchester, MA 01890
      2 Fairfield Place, Winchester, MA 01890
      /42

      Est $2,081,694 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 3,746 Sq Ft

      2 Fairfield Place, Winchester, MA 01890

      2 Fairfield Place, Winchester, MA 01890
  • 89 Main St, Winchester, MA 01890
    89 Main St, Winchester, MA 01890
    89 Main St, 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
    • 50 Lake St Unit I, Winchester, MA 01890
      50 Lake St Unit I, Winchester, MA 01890
      50 Lake St Unit I, Winchester, MA 01890
      /38

      Est $694,490 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,461 Sq Ft

      50 Lake St Unit I, Winchester, MA 01890

      50 Lake St Unit I, Winchester, MA 01890
  • 3 Socrates Way, Winchester, MA 01890
    3 Socrates Way, Winchester, MA 01890
    3 Socrates Way, 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 $1,282,983

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

    3 Socrates Way, Winchester, MA 01890
    • 50 Lake St Unit H, Winchester, MA 01890
      50 Lake St Unit H, Winchester, MA 01890
      50 Lake St Unit H, Winchester, MA 01890
      /42

      Est $710,129 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,407 Sq Ft

      50 Lake St Unit H, Winchester, MA 01890

      50 Lake St Unit H, Winchester, MA 01890

Showing Results 321 - 360, Page 9 of 18

Massachusetts Middlesex County Winchester

Real Estate & Homes

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

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group