1,744

West Side Homes

Section Image
    • 67 Edward Dr, Winchester, MA 01890
      67 Edward Dr, Winchester, MA 01890
      67 Edward Dr, Winchester, MA 01890
      /39

      Est $1,079,212

      Not Listed For Sale

      67 Edward Dr, Winchester, MA 01890

      • 2 Beds
      • 3 Baths
      • 2,954 Sq Ft
      • Built 1985
      67 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 42 Days On Market

      Last Listing Agent Ann Norberg Coldwell Banker Realty - Lexington

    • 44 Edward Dr, Winchester, MA 01890
      44 Edward Dr, Winchester, MA 01890
      44 Edward Dr, Winchester, MA 01890
      /30

      Est $1,079,196

      Not Listed For Sale

      44 Edward Dr, Winchester, MA 01890

      • 3 Beds
      • 4 Baths
      • 2,870 Sq Ft
      • Built 1987
      44 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 262 Days On Market

      Last Listing Agent Lucille Murray Gibson Sotheby's International Realty

    • 32 Edward Dr, Winchester, MA 01890
      32 Edward Dr, Winchester, MA 01890
      32 Edward Dr, Winchester, MA 01890
      /25

      Est $1,125,216

      Not Listed For Sale

      32 Edward Dr, Winchester, MA 01890

      • 3 Beds
      • 4 Baths
      • 2,859 Sq Ft
      • Built 1985
      32 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Mary Errico Barrett Sotheby's International Realty

    • 28 Edward Dr, Winchester, MA 01890
      28 Edward Dr, Winchester, MA 01890
      28 Edward Dr, Winchester, MA 01890
      /13

      Est $985,122

      Not Listed For Sale

      28 Edward Dr, Winchester, MA 01890

      • 2 Beds
      • 3 Baths
      • 1,909 Sq Ft
      • Built 1985
      28 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Freda Realty Group Leading Edge Real Estate

    • 15 Edward Dr, Winchester, MA 01890
      15 Edward Dr, Winchester, MA 01890
      15 Edward Dr, Winchester, MA 01890
      /18

      Est $1,066,626

      Not Listed For Sale

      15 Edward Dr, Winchester, MA 01890

      • 2 Beds
      • 3 Baths
      • 1,916 Sq Ft
      • Built 1985
      15 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent Danielle Devarne Compass

    • 282 High St, Winchester, MA 01890
      282 High St, Winchester, MA 01890
      /2

      Est $2,937,566

      Not Listed For Sale

      282 High St, Winchester, MA 01890

      • 6 Beds
      • 5 Baths
      • 6,583 Sq Ft
      • Built 1995
      282 High St, Winchester, MA 01890

    • 11 Edward Dr, Winchester, MA 01890
      11 Edward Dr, Winchester, MA 01890
      11 Edward Dr, Winchester, MA 01890
      /20

      Est $1,175,153

      Not Listed For Sale

      11 Edward Dr, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 1,898 Sq Ft
      • Built 1972
      11 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Ida Bianco Coldwell Banker Realty - Lexington

    • 272 High St, Winchester, MA 01890
      272 High St, Winchester, MA 01890
      272 High St, Winchester, MA 01890
      /42

      Est $2,352,154

      Not Listed For Sale

      272 High St, Winchester, MA 01890

      • 4 Beds
      • 4 Baths
      • 4,215 Sq Ft
      • Built 1995
      272 High St, Winchester, MA 01890

      Last Sold Summary

      • 193 Days On Market

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

    • 10 Pepper Hill Dr, Winchester, MA 01890
      10 Pepper Hill Dr, Winchester, MA 01890
      10 Pepper Hill Dr, Winchester, MA 01890
      /30

      Est $1,884,998

      Not Listed For Sale

      10 Pepper Hill Dr, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 3,590 Sq Ft
      • Built 1977
      10 Pepper Hill Dr, Winchester, MA 01890

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Laura McCaughey Waterfield Sotheby's International Realty

    • 62 Ridge St, Winchester, MA 01890
      62 Ridge St, Winchester, MA 01890
      62 Ridge St, Winchester, MA 01890
      /11

      Est $1,493,335

      Not Listed For Sale

      62 Ridge St, Winchester, MA 01890

      • 4 Beds
      • 3 Baths
      • 2,788 Sq Ft
      • Built 1970
      62 Ridge St, Winchester, MA 01890

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Rachel Ventresca Greater Metropolitan R. E.

    • 6 Skyline Dr, Winchester, MA 01890
      6 Skyline Dr, Winchester, MA 01890
      6 Skyline Dr, Winchester, MA 01890
      /31

      Est $1,414,658

      Not Listed For Sale

      6 Skyline Dr, Winchester, MA 01890

      • 4 Beds
      • 3 Baths
      • 1,927 Sq Ft
      • Built 1965
      6 Skyline Dr, Winchester, MA 01890

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Charles Ginsberg Coldwell Banker Realty - Lexington

    • 6 Edward Dr, Winchester, MA 01890
      6 Edward Dr, Winchester, MA 01890
      6 Edward Dr, Winchester, MA 01890
      /33

      Est $1,517,822

      Not Listed For Sale

      6 Edward Dr, Winchester, MA 01890

      • 4 Beds
      • 3 Baths
      • 2,256 Sq Ft
      • Built 1970
      6 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Sharon Tang U3 Realty, LLC

    • 3 Edward Dr, Winchester, MA 01890
      3 Edward Dr, Winchester, MA 01890
      3 Edward Dr, Winchester, MA 01890
      /30

      Est $1,951,114

      Not Listed For Sale

      3 Edward Dr, Winchester, MA 01890

      • 4 Beds
      • 4 Baths
      • 3,414 Sq Ft
      • Built 2004
      3 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 46 Days On Market

      Last Listing Agent Sven Andersen Keller Williams Realty Boston Northwest

    • 16 James St, Winchester, MA 01890
      16 James St, Winchester, MA 01890
      16 James St, Winchester, MA 01890
      /25

      Est $1,138,727

      Not Listed For Sale

      16 James St, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 1,600 Sq Ft
      • Built 1965
      16 James St, Winchester, MA 01890

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Derek Greene The Greene Realty Group

    • 2 James St, Winchester, MA 01890
      2 James St, Winchester, MA 01890
      2 James St, Winchester, MA 01890
      /20

      Est $1,124,037

      Not Listed For Sale

      2 James St, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 1,909 Sq Ft
      • Built 1955
      2 James St, Winchester, MA 01890

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Jing Chen Boston Hub Real Estate

    • 3 James St, Winchester, MA 01890
      3 James St, Winchester, MA 01890
      3 James St, Winchester, MA 01890
      /28

      Est $1,359,438

      Not Listed For Sale

      3 James St, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 1,794 Sq Ft
      • Built 1952
      3 James St, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Susan Gilbert Phillips The Higgins Group REALTORS®

    • 178 Dothan St, Winchester, MA 01890
      178 Dothan St, Winchester, MA 01890
      178 Dothan St, Winchester, MA 01890
      /12

      Est $1,558,677

      Not Listed For Sale

      178 Dothan St, Winchester, MA 01890

      • 3 Beds
      • 4 Baths
      • 2,600 Sq Ft
      • Built 2005
      178 Dothan St, Winchester, MA 01890

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Nancy O'Herron Lexington / Winchester Regional Office

    • 186 Dothan St, Winchester, MA 01890
      186 Dothan St, Winchester, MA 01890
      186 Dothan St, Winchester, MA 01890
      /25

      Est $1,388,759

      Not Listed For Sale

      186 Dothan St, Winchester, MA 01890

      • 4 Beds
      • 3 Baths
      • 2,624 Sq Ft
      • Built 1900
      186 Dothan St, Winchester, MA 01890

      Last Sold Summary

      • 38 Days On Market

      Last Listing Agent Dan Fabbri Century 21 North East

    • 15 James St, Winchester, MA 01890
      15 James St, Winchester, MA 01890
      15 James St, Winchester, MA 01890
      /30

      Est $1,592,943

      Not Listed For Sale

      15 James St, Winchester, MA 01890

      • 4 Beds
      • 4 Baths
      • 2,447 Sq Ft
      • Built 1945
      15 James St, Winchester, MA 01890

      Last Sold Summary

      • 51 Days On Market

      Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    • 27 James St, Winchester, MA 01890
      27 James St, Winchester, MA 01890
      27 James St, Winchester, MA 01890
      /30

      Est $1,187,793

      Not Listed For Sale

      27 James St, Winchester, MA 01890

      • 5 Beds
      • 2 Baths
      • 1,690 Sq Ft
      • Built 1945
      27 James St, Winchester, MA 01890

      Last Sold Summary

      • 82 Days On Market

      Last Listing Agent Ciampa Team LAER Realty Partners

    • 30 James St, Winchester, MA 01890
      30 James St, Winchester, MA 01890
      /2

      Est $903,056

      Not Listed For Sale

      30 James St, Winchester, MA 01890

      • 2 Beds
      • 1 Bath
      • 1,200 Sq Ft
      • Built 1948
      30 James St, Winchester, MA 01890

    • 19 Henry St, Winchester, MA 01890
      19 Henry St, Winchester, MA 01890
      19 Henry St, Winchester, MA 01890
      /15

      Est $1,103,336

      Not Listed For Sale

      19 Henry St, Winchester, MA 01890

      • 4 Beds
      • 2 Baths
      • 1,776 Sq Ft
      • Built 1921
      19 Henry St, Winchester, MA 01890

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Susan Guarino Lyv Realty

    • 49 Henry St, Winchester, MA 01890
      49 Henry St, Winchester, MA 01890
      49 Henry St, Winchester, MA 01890
      /28

      Est $1,686,034

      Not Listed For Sale

      49 Henry St, Winchester, MA 01890

      • 5 Beds
      • 4 Baths
      • 3,238 Sq Ft
      • Built 1956
      49 Henry St, Winchester, MA 01890

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Anthony Menounos Coldwell Banker Realty - Boston

    • 53 Henry St, Winchester, MA 01890
      53 Henry St, Winchester, MA 01890
      53 Henry St, Winchester, MA 01890
      /23

      Est $1,116,969

      Not Listed For Sale

      53 Henry St, Winchester, MA 01890

      • 3 Beds
      • 3 Baths
      • 1,727 Sq Ft
      • Built 1917
      53 Henry St, Winchester, MA 01890

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Alice Kirk Barrett Sotheby's International Realty

    • 11 Henry St, Winchester, MA 01890
      11 Henry St, Winchester, MA 01890
      11 Henry St, Winchester, MA 01890
      /30

      Est $1,510,199

      Not Listed For Sale

      11 Henry St, Winchester, MA 01890

      • 4 Beds
      • 3 Baths
      • 2,651 Sq Ft
      • Built 1938
      11 Henry St, Winchester, MA 01890

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

    • 90 Dunster Ln, Winchester, MA 01890
      90 Dunster Ln, Winchester, MA 01890
      90 Dunster Ln, Winchester, MA 01890
      /15

      Est $2,049,127

      Not Listed For Sale

      90 Dunster Ln, Winchester, MA 01890

      • 4 Beds
      • 4 Baths
      • 3,247 Sq Ft
      • Built 2014
      90 Dunster Ln, Winchester, MA 01890

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Peter Vaillancout EXIT Cape Realty

    • 64 Dunster Ln, Winchester, MA 01890
      64 Dunster Ln, Winchester, MA 01890
      64 Dunster Ln, Winchester, MA 01890
      /29

      Est $2,336,116

      Not Listed For Sale

      64 Dunster Ln, Winchester, MA 01890

      • 5 Beds
      • 4 Baths
      • 4,000 Sq Ft
      • Built 2016
      64 Dunster Ln, Winchester, MA 01890

      Last Sold Summary

      • 58 Days On Market

      Last Listing Agent Anthony Menounos Coldwell Banker Realty - Boston

    • 36 Dunster Ln, Winchester, MA 01890
      36 Dunster Ln, Winchester, MA 01890
      36 Dunster Ln, Winchester, MA 01890
      /40

      Est $2,193,946

      Not Listed For Sale

      36 Dunster Ln, Winchester, MA 01890

      • 4 Beds
      • 4 Baths
      • 3,967 Sq Ft
      • Built 2020
      36 Dunster Ln, Winchester, MA 01890

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Robert Bowes Gibson Sotheby's International Realty

    • 21 Locke St, Winchester, MA 01890
      21 Locke St, Winchester, MA 01890
      /2

      Est $1,258,583

      Not Listed For Sale

      21 Locke St, Winchester, MA 01890

      • 4 Beds
      • 2 Baths
      • 2,238 Sq Ft
      • Built 1952
      21 Locke St, Winchester, MA 01890

    • 67 Dunster Ln, Winchester, MA 01890
      67 Dunster Ln, Winchester, MA 01890
      67 Dunster Ln, Winchester, MA 01890
      /32

      Est $827,650

      Not Listed For Sale

      67 Dunster Ln, Winchester, MA 01890

      • 2 Beds
      • 1 Bath
      • 1,137 Sq Ft
      • Built 1920
      67 Dunster Ln, Winchester, MA 01890

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    • 41 Dunster Ln, Winchester, MA 01890
      41 Dunster Ln, Winchester, MA 01890
      41 Dunster Ln, Winchester, MA 01890
      /30

      Est $2,344,097

      Not Listed For Sale

      41 Dunster Ln, Winchester, MA 01890

      • 5 Beds
      • 4 Baths
      • 3,780 Sq Ft
      • Built 2014
      41 Dunster Ln, Winchester, MA 01890

      Last Sold Summary

      • 62 Days On Market

      Last Listing Agent Jonathan Nyberg Old New England Properties

    • 33 Dunster Ln, Winchester, MA 01890
      33 Dunster Ln, Winchester, MA 01890
      33 Dunster Ln, Winchester, MA 01890
      /24

      Est $2,088,121

      Not Listed For Sale

      33 Dunster Ln, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 1,939 Sq Ft
      • Built 1930
      33 Dunster Ln, Winchester, MA 01890

      Last Sold Summary

      • 106 Days On Market

      Last Listing Agent Diane Plunkett Plunkett Properties

    • 27 Dunster Ln, Winchester, MA 01890
      27 Dunster Ln, Winchester, MA 01890
      27 Dunster Ln, Winchester, MA 01890
      /12

      Est $1,123,524

      Not Listed For Sale

      27 Dunster Ln, Winchester, MA 01890

      • 3 Beds
      • 1 Bath
      • 1,475 Sq Ft
      • Built 1929
      27 Dunster Ln, Winchester, MA 01890

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Linda Sharpe William Raveis R.E. & Home Services

    • 30 Ridge St, Winchester, MA 01890
      30 Ridge St, Winchester, MA 01890
      30 Ridge St, Winchester, MA 01890
      /27

      Est $1,632,672

      Not Listed For Sale

      30 Ridge St, Winchester, MA 01890

      • 3 Beds
      • 3 Baths
      • 2,211 Sq Ft
      • Built 1963
      30 Ridge St, Winchester, MA 01890

      Last Sold Summary

      • 9 Days On Market

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

    • 191 High St, Winchester, MA 01890
      191 High St, Winchester, MA 01890
      191 High St, Winchester, MA 01890
      /21

      Est $2,408,788

      Not Listed For Sale

      191 High St, Winchester, MA 01890

      • 4 Beds
      • 4 Baths
      • 4,032 Sq Ft
      • Built 2003
      191 High St, Winchester, MA 01890

      Last Sold Summary

      • 84 Days On Market

      Last Listing Agent Dorothea Feffer Churchill Properties

    • 6 Azalea Rd, Winchester, MA 01890
      6 Azalea Rd, Winchester, MA 01890
      6 Azalea Rd, Winchester, MA 01890
      /10

      Est $2,652,838

      Not Listed For Sale

      6 Azalea Rd, Winchester, MA 01890

      • 3 Beds
      • 3 Baths
      • 2,000 Sq Ft
      • Built 2013
      6 Azalea Rd, Winchester, MA 01890

      Last Sold Summary

      • 139 Days On Market

      Last Listing Agent Steve McKenna Gibson Sotheby's International Realty

    • 8 Azalea Rd, Winchester, MA 01890
      8 Azalea Rd, Winchester, MA 01890
      8 Azalea Rd, Winchester, MA 01890
      /9

      Est $2,434,664

      Not Listed For Sale

      8 Azalea Rd, Winchester, MA 01890

      • 2 Beds
      • 3 Baths
      • 2,297 Sq Ft
      • Built 2013
      8 Azalea Rd, Winchester, MA 01890

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Steve McKenna Gibson Sotheby's International Realty

    • 10 Azalea Rd, Winchester, MA 01890
      10 Azalea Rd, Winchester, MA 01890
      10 Azalea Rd, Winchester, MA 01890
      /9

      Est $2,185,001

      Not Listed For Sale

      10 Azalea Rd, Winchester, MA 01890

      • 2 Beds
      • 3 Baths
      • 2,000 Sq Ft
      • Built 2013
      10 Azalea Rd, Winchester, MA 01890

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Steve McKenna Gibson Sotheby's International Realty

    • 3 Thoreau Cir, Winchester, MA 01890
      3 Thoreau Cir, Winchester, MA 01890
      /2

      Est $2,271,940

      Not Listed For Sale

      3 Thoreau Cir, Winchester, MA 01890

      • 5 Beds
      • 3 Baths
      • 4,764 Sq Ft
      • Built 1978
      3 Thoreau Cir, Winchester, MA 01890

    • 4 Thoreau Cir, Winchester, MA 01890
      4 Thoreau Cir, Winchester, MA 01890
      4 Thoreau Cir, Winchester, MA 01890
      /29

      Est $1,722,495

      Not Listed For Sale

      4 Thoreau Cir, Winchester, MA 01890

      • 3 Beds
      • 3 Baths
      • 3,338 Sq Ft
      • Built 1980
      4 Thoreau Cir, Winchester, MA 01890

      Last Sold Summary

      • 119 Days On Market

      Last Listing Agent Sven Andersen Keller Williams Realty Boston Northwest

Showing Results 481 - 520, Page 13 of 18

Massachusetts Middlesex County Winchester

Real Estate & Homes

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

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