1,775

West Side Homes

Section Image
    • 7 Wainwright Rd Unit 56, Winchester, MA 01890
      7 Wainwright Rd Unit 56, Winchester, MA 01890
      7 Wainwright Rd Unit 56, Winchester, MA 01890
      /42

      Est $1,389,222 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 3,074 Sq Ft

      7 Wainwright Rd Unit 56, Winchester, MA 01890

      7 Wainwright Rd Unit 56, Winchester, MA 01890
    • 7 Wainwright Rd Unit 55, Winchester, MA 01890
      7 Wainwright Rd Unit 55, Winchester, MA 01890
      7 Wainwright Rd Unit 55, Winchester, MA 01890
      /42

      Est $1,639,761 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 4,228 Sq Ft

      7 Wainwright Rd Unit 55, Winchester, MA 01890

      7 Wainwright Rd Unit 55, Winchester, MA 01890
    • 7 Wainwright Rd Unit 54, Winchester, MA 01890
      7 Wainwright Rd Unit 54, Winchester, MA 01890
      7 Wainwright Rd Unit 54, Winchester, MA 01890
      /42

      Est $1,847,079 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 4,808 Sq Ft

      7 Wainwright Rd Unit 54, Winchester, MA 01890

      7 Wainwright Rd Unit 54, Winchester, MA 01890
    • 7 Wainwright Rd Unit 50, Winchester, MA 01890
      7 Wainwright Rd Unit 50, Winchester, MA 01890
      7 Wainwright Rd Unit 50, Winchester, MA 01890
      /42

      Est $1,733,317 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 3,206 Sq Ft

      7 Wainwright Rd Unit 50, Winchester, MA 01890

      7 Wainwright Rd Unit 50, Winchester, MA 01890
    • 7 Wainwright Rd Unit 44, Winchester, MA 01890
      7 Wainwright Rd Unit 44, Winchester, MA 01890
      7 Wainwright Rd Unit 44, Winchester, MA 01890
      /28

      Est $1,329,688 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,740 Sq Ft

      7 Wainwright Rd Unit 44, Winchester, MA 01890

      7 Wainwright Rd Unit 44, Winchester, MA 01890
    • 8 Wainwright Rd, Winchester, MA 01890
      8 Wainwright Rd, Winchester, MA 01890
      8 Wainwright Rd, Winchester, MA 01890
      /41

      Est $1,852,145 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 3,246 Sq Ft

      8 Wainwright Rd, Winchester, MA 01890

      8 Wainwright Rd, Winchester, MA 01890
    • 41 Amberwood Dr, Winchester, MA 01890
      41 Amberwood Dr, Winchester, MA 01890
      41 Amberwood Dr, Winchester, MA 01890
      /40

      Est $2,282,944 Not Listed For Sale

      • 4 Beds
      • 5 Baths
      • 3,903 Sq Ft

      41 Amberwood Dr, Winchester, MA 01890

      41 Amberwood Dr, Winchester, MA 01890
    • 49 Amberwood Dr, Winchester, MA 01890
      49 Amberwood Dr, Winchester, MA 01890
      49 Amberwood Dr, Winchester, MA 01890
      /36

      Est $1,861,890 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,200 Sq Ft

      49 Amberwood Dr, Winchester, MA 01890

      49 Amberwood Dr, Winchester, MA 01890
    • 24 Surrey Rd, Winchester, MA 01890
      24 Surrey Rd, Winchester, MA 01890
      24 Surrey Rd, Winchester, MA 01890
      /33

      Est $2,466,927 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 4,158 Sq Ft

      24 Surrey Rd, Winchester, MA 01890

      24 Surrey Rd, Winchester, MA 01890
    • 23 Johnson Rd, Winchester, MA 01890
      23 Johnson Rd, Winchester, MA 01890
      23 Johnson Rd, Winchester, MA 01890
      /23

      Est $1,294,007 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,263 Sq Ft

      23 Johnson Rd, Winchester, MA 01890

      23 Johnson Rd, Winchester, MA 01890
    • 3 Amberwood Dr, Winchester, MA 01890
      3 Amberwood Dr, Winchester, MA 01890
      3 Amberwood Dr, Winchester, MA 01890
      /27

      Est $1,608,689 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,168 Sq Ft

      3 Amberwood Dr, Winchester, MA 01890

      3 Amberwood Dr, Winchester, MA 01890
    • 15 Amberwood Dr, Winchester, MA 01890
      15 Amberwood Dr, Winchester, MA 01890
      15 Amberwood Dr, Winchester, MA 01890
      /42

      Est $2,342,432 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 5,036 Sq Ft

      15 Amberwood Dr, Winchester, MA 01890

      15 Amberwood Dr, Winchester, MA 01890
    • 22 Amberwood Dr, Winchester, MA 01890
      22 Amberwood Dr, Winchester, MA 01890
      22 Amberwood Dr, Winchester, MA 01890
      /42

      Est $2,502,828 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 5,016 Sq Ft

      22 Amberwood Dr, Winchester, MA 01890

      22 Amberwood Dr, Winchester, MA 01890
    • 376 Cambridge St, Winchester, MA 01890
      376 Cambridge St, Winchester, MA 01890
      376 Cambridge St, Winchester, MA 01890
      /40

      Est $1,015,662 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,791 Sq Ft

      376 Cambridge St, Winchester, MA 01890

      376 Cambridge St, Winchester, MA 01890
    • 372 Cambridge St, Winchester, MA 01890
      372 Cambridge St, Winchester, MA 01890
      372 Cambridge St, Winchester, MA 01890
      /34

      Est $1,067,056 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 1,925 Sq Ft

      372 Cambridge St, Winchester, MA 01890

      372 Cambridge St, Winchester, MA 01890
    • 3 Bigelow Ave, Winchester, MA 01890
      3 Bigelow Ave, Winchester, MA 01890
      3 Bigelow Ave, Winchester, MA 01890
      /42

      Est $1,929,177 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,400 Sq Ft

      3 Bigelow Ave, Winchester, MA 01890

      3 Bigelow Ave, Winchester, MA 01890
    • 3 Pilgrim Dr, Winchester, MA 01890
      3 Pilgrim Dr, Winchester, MA 01890
      3 Pilgrim Dr, Winchester, MA 01890
      /42

      Est $2,957,820 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 6,267 Sq Ft

      3 Pilgrim Dr, Winchester, MA 01890

      3 Pilgrim Dr, Winchester, MA 01890
    • 7 Aristotle Dr, Winchester, MA 01890
      7 Aristotle Dr, Winchester, MA 01890
      7 Aristotle Dr, Winchester, MA 01890
      /42

      Est $2,134,225 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,652 Sq Ft

      7 Aristotle Dr, Winchester, MA 01890

      7 Aristotle Dr, Winchester, MA 01890
    • 7 Longfellow Rd, Winchester, MA 01890
      7 Longfellow Rd, Winchester, MA 01890
      7 Longfellow Rd, Winchester, MA 01890
      /42

      Est $1,765,173 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,598 Sq Ft

      7 Longfellow Rd, Winchester, MA 01890

      7 Longfellow Rd, Winchester, MA 01890
    • 11 Olde Lyme Rd, Winchester, MA 01890
      11 Olde Lyme Rd, Winchester, MA 01890
      11 Olde Lyme Rd, Winchester, MA 01890
      /31

      Est $2,004,751 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,256 Sq Ft

      11 Olde Lyme Rd, Winchester, MA 01890

      11 Olde Lyme Rd, Winchester, MA 01890
    • 251 Ridge St, Winchester, MA 01890
      251 Ridge St, Winchester, MA 01890
      251 Ridge St, Winchester, MA 01890
      /34

      Est $1,403,676 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,842 Sq Ft

      251 Ridge St, Winchester, MA 01890

      251 Ridge St, Winchester, MA 01890
    • 67 Edward Dr, Winchester, MA 01890
      67 Edward Dr, Winchester, MA 01890
      67 Edward Dr, Winchester, MA 01890
      /39

      Est $1,051,387 Not Listed For Sale

      • 2 Beds
      • 3 Baths
      • 2,954 Sq Ft

      67 Edward Dr, Winchester, MA 01890

      67 Edward Dr, Winchester, MA 01890
    • 36 Edward Dr, Winchester, MA 01890
      36 Edward Dr, Winchester, MA 01890
      36 Edward Dr, Winchester, MA 01890
      /34

      Est $1,080,163 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,859 Sq Ft

      36 Edward Dr, Winchester, MA 01890

      36 Edward Dr, Winchester, MA 01890
    • 31 Edward Dr, Winchester, MA 01890
      31 Edward Dr, Winchester, MA 01890
      31 Edward Dr, Winchester, MA 01890
      /42

      Est $1,048,220 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,793 Sq Ft

      31 Edward Dr, Winchester, MA 01890

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

      Est $1,518,309 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,256 Sq Ft

      6 Edward Dr, Winchester, MA 01890

      6 Edward Dr, Winchester, MA 01890
    • 2 James St, Winchester, MA 01890
      2 James St, Winchester, MA 01890
      2 James St, Winchester, MA 01890
      /20

      Est $1,150,010 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,909 Sq Ft

      2 James St, Winchester, MA 01890

      2 James St, Winchester, MA 01890
    • 180 Dothan St, Winchester, MA 01890
      180 Dothan St, Winchester, MA 01890
      180 Dothan St, Winchester, MA 01890
      /33

      Est $1,121,403 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,878 Sq Ft

      180 Dothan St, Winchester, MA 01890

      180 Dothan St, Winchester, MA 01890
    • 23 Henry St, Winchester, MA 01890
      23 Henry St, Winchester, MA 01890
      23 Henry St, Winchester, MA 01890
      /33

      Est $1,305,515 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,924 Sq Ft

      23 Henry St, Winchester, MA 01890

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

      Est $1,133,429 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,727 Sq Ft

      53 Henry St, Winchester, MA 01890

      53 Henry St, Winchester, MA 01890
    • 50 Henry St, Winchester, MA 01890
      50 Henry St, Winchester, MA 01890
      50 Henry St, Winchester, MA 01890
      /8

      Est $1,077,058 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,840 Sq Ft

      50 Henry St, Winchester, MA 01890

      50 Henry St, Winchester, MA 01890
    • 6 Ridge St, Winchester, MA 01890
      6 Ridge St, Winchester, MA 01890
      6 Ridge St, Winchester, MA 01890
      /37

      Est $2,132,685 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,346 Sq Ft

      6 Ridge St, Winchester, MA 01890

      6 Ridge St, Winchester, MA 01890
    • 20 Coolidge Rd, Winchester, MA 01890
      20 Coolidge Rd, Winchester, MA 01890
      20 Coolidge Rd, Winchester, MA 01890
      /40

      Est $1,829,710 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 3,250 Sq Ft

      20 Coolidge Rd, Winchester, MA 01890

      20 Coolidge Rd, Winchester, MA 01890
    • 1 Windsong Ln, Winchester, MA 01890
      1 Windsong Ln, Winchester, MA 01890
      1 Windsong Ln, Winchester, MA 01890
      /41

      Est $2,213,033 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 4,875 Sq Ft

      1 Windsong Ln, Winchester, MA 01890

      1 Windsong Ln, Winchester, MA 01890
    • 21 Olde Village Dr, Winchester, MA 01890
      21 Olde Village Dr, Winchester, MA 01890
      21 Olde Village Dr, Winchester, MA 01890
      /27

      Est $2,432,187 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 5,476 Sq Ft

      21 Olde Village Dr, Winchester, MA 01890

      21 Olde Village Dr, Winchester, MA 01890
    • 25 Olde Village Dr, Winchester, MA 01890
      25 Olde Village Dr, Winchester, MA 01890
      25 Olde Village Dr, Winchester, MA 01890
      /34

      Est $2,886,447 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 7,235 Sq Ft

      25 Olde Village Dr, Winchester, MA 01890

      25 Olde Village Dr, Winchester, MA 01890
    • 18 Olde Village Dr, Winchester, MA 01890
      18 Olde Village Dr, Winchester, MA 01890
      18 Olde Village Dr, Winchester, MA 01890
      /22

      Est $2,725,091 Not Listed For Sale

      • 5 Beds
      • 5.5 Baths
      • 5,333 Sq Ft

      18 Olde Village Dr, Winchester, MA 01890

      18 Olde Village Dr, Winchester, MA 01890
    • 139 High St, Winchester, MA 01890
      139 High St, Winchester, MA 01890
      139 High St, Winchester, MA 01890
      /26

      Est $1,061,745 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,302 Sq Ft

      139 High St, Winchester, MA 01890

      139 High St, Winchester, MA 01890
    • 172 High St, Winchester, MA 01890
      172 High St, Winchester, MA 01890
      172 High St, Winchester, MA 01890
      /10

      Est $2,160,306 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,714 Sq Ft

      172 High St, Winchester, MA 01890

      172 High St, Winchester, MA 01890
    • 196 High St, Winchester, MA 01890
      196 High St, Winchester, MA 01890
      196 High St, Winchester, MA 01890
      /20

      Est $2,272,354 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,732 Sq Ft

      196 High St, Winchester, MA 01890

      196 High St, Winchester, MA 01890
    • 9 Lockeland Rd, Winchester, MA 01890
      9 Lockeland Rd, Winchester, MA 01890
      9 Lockeland Rd, Winchester, MA 01890
      /33

      Est $2,398,031 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,587 Sq Ft

      9 Lockeland Rd, Winchester, MA 01890

      9 Lockeland Rd, Winchester, MA 01890

Showing Results 201 - 240, Page 6 of 18

Massachusetts Middlesex County Winchester West Side

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.

Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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 © 2025 CoStar Group