1,778

West Side Homes

Section Image
    • 111 Arlington St, Winchester, MA 01890
      111 Arlington St, Winchester, MA 01890
      111 Arlington St, Winchester, MA 01890
      /36

      Est $2,165,017 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 2,871 Sq Ft

      111 Arlington St, Winchester, MA 01890

      111 Arlington St, Winchester, MA 01890
    • 108 Arlington St, Winchester, MA 01890
      108 Arlington St, Winchester, MA 01890
      108 Arlington St, Winchester, MA 01890
      /41

      Est $2,903,940 Not Listed For Sale

      • 5 Beds
      • 7 Baths
      • 5,830 Sq Ft

      108 Arlington St, Winchester, MA 01890

      108 Arlington St, Winchester, MA 01890
    • 20 Westland Ave, Winchester, MA 01890
      20 Westland Ave, Winchester, MA 01890
      20 Westland Ave, Winchester, MA 01890
      /42

      Est $2,183,464 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,400 Sq Ft

      20 Westland Ave, Winchester, MA 01890

      20 Westland Ave, Winchester, MA 01890
    • 8 Sachem Rd, Winchester, MA 01890
      8 Sachem Rd, Winchester, MA 01890
      8 Sachem Rd, Winchester, MA 01890
      /40

      Est $1,813,623 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 3,205 Sq Ft

      8 Sachem Rd, Winchester, MA 01890

      8 Sachem Rd, Winchester, MA 01890
    • 1 Indian Hill Rd, Winchester, MA 01890
      1 Indian Hill Rd, Winchester, MA 01890
      1 Indian Hill Rd, Winchester, MA 01890
      /25

      Est $1,803,480 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 2,682 Sq Ft

      1 Indian Hill Rd, Winchester, MA 01890

      1 Indian Hill Rd, Winchester, MA 01890
    • 10 Westland Ave, Winchester, MA 01890
      10 Westland Ave, Winchester, MA 01890
      10 Westland Ave, Winchester, MA 01890
      /40

      Est $1,521,700 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,071 Sq Ft

      10 Westland Ave, Winchester, MA 01890

      10 Westland Ave, Winchester, MA 01890
    • 152 Hutchinson Rd, Arlington, MA 02474
      152 Hutchinson Rd, Arlington, MA 02474
      152 Hutchinson Rd, Arlington, MA 02474
      /36

      Est $1,791,187 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,189 Sq Ft

      152 Hutchinson Rd, Arlington, MA 02474

      152 Hutchinson Rd, Arlington, MA 02474
    • 78 Dunster Ln, Winchester, MA 01890
      78 Dunster Ln, Winchester, MA 01890
      78 Dunster Ln, Winchester, MA 01890
      /41

      Est $1,630,428 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,676 Sq Ft

      78 Dunster Ln, Winchester, MA 01890

      78 Dunster Ln, Winchester, MA 01890
    • 29 Gershon Way Unit 29, Winchester, MA 01890
      29 Gershon Way Unit 29, Winchester, MA 01890
      29 Gershon Way Unit 29, Winchester, MA 01890
      /35

      Est $2,360,735 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 4,138 Sq Ft

      29 Gershon Way Unit 29, Winchester, MA 01890

      29 Gershon Way Unit 29, Winchester, MA 01890
    • 26 Gershon Way Unit 26, Winchester, MA 01890
      26 Gershon Way Unit 26, Winchester, MA 01890
      26 Gershon Way Unit 26, Winchester, MA 01890
      /38

      Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,638 Sq Ft

      26 Gershon Way Unit 26, Winchester, MA 01890

      26 Gershon Way Unit 26, Winchester, MA 01890
    • 29 Edward Dr Unit 29, Winchester, MA 01890
      29 Edward Dr Unit 29, Winchester, MA 01890
      29 Edward Dr Unit 29, Winchester, MA 01890
      /30

      Est $1,042,182 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,679 Sq Ft

      29 Edward Dr Unit 29, Winchester, MA 01890

      29 Edward Dr Unit 29, Winchester, MA 01890
    • 27 Gershon Way Unit 27, Winchester, MA 01890
      27 Gershon Way Unit 27, Winchester, MA 01890
      27 Gershon Way Unit 27, Winchester, MA 01890
      /38

      Est $2,003,734 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,638 Sq Ft

      27 Gershon Way Unit 27, Winchester, MA 01890

      27 Gershon Way Unit 27, Winchester, MA 01890
    • 24 Gershon Way Unit 24, Winchester, MA 01890
      24 Gershon Way Unit 24, Winchester, MA 01890
      24 Gershon Way Unit 24, Winchester, MA 01890
      /39

      Est $1,856,657 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,638 Sq Ft

      24 Gershon Way Unit 24, Winchester, MA 01890

      24 Gershon Way Unit 24, Winchester, MA 01890
    • 4 Andrews Rd, Winchester, MA 01890
      4 Andrews Rd, Winchester, MA 01890
      4 Andrews Rd, Winchester, MA 01890
      /31

      Est $2,821,417 Not Listed For Sale

      • 4 Beds
      • 5 Baths
      • 6,026 Sq Ft

      4 Andrews Rd, Winchester, MA 01890

      4 Andrews Rd, Winchester, MA 01890
    • 5 Wagon Wheel Rd, Winchester, MA 01890
      5 Wagon Wheel Rd, Winchester, MA 01890
      5 Wagon Wheel Rd, Winchester, MA 01890
      /35

      Est $3,765,105 Not Listed For Sale

      • 6 Beds
      • 6 Baths
      • 7,097 Sq Ft

      5 Wagon Wheel Rd, Winchester, MA 01890

      5 Wagon Wheel Rd, Winchester, MA 01890
    • 6 Johnson Rd, Winchester, MA 01890
      6 Johnson Rd, Winchester, MA 01890
      6 Johnson Rd, Winchester, MA 01890
      /42

      Est $3,123,926 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 6,003 Sq Ft

      6 Johnson Rd, Winchester, MA 01890

      6 Johnson Rd, Winchester, MA 01890
    • 0 Red Coach Ln, Winchester, MA 01890
      0 Red Coach Ln, Winchester, MA 01890
      0 Red Coach Ln, Winchester, MA 01890
      /18

      Not Listed For Sale

      0 Red Coach Ln, Winchester, MA 01890

      0 Red Coach Ln, Winchester, MA 01890
    • 5 Fieldstone Dr, Winchester, MA 01890
      5 Fieldstone Dr, Winchester, MA 01890
      5 Fieldstone Dr, Winchester, MA 01890
      /32

      Est $1,989,162 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,694 Sq Ft

      5 Fieldstone Dr, Winchester, MA 01890

      5 Fieldstone Dr, Winchester, MA 01890
    • 58 Squire Rd, Winchester, MA 01890
      58 Squire Rd, Winchester, MA 01890
      58 Squire Rd, Winchester, MA 01890
      /38

      Est $1,475,614 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,300 Sq Ft

      58 Squire Rd, Winchester, MA 01890

      58 Squire Rd, Winchester, MA 01890
    • 208 Ridge St, Winchester, MA 01890
      208 Ridge St, Winchester, MA 01890
      208 Ridge St, Winchester, MA 01890
      /42

      Est $2,219,323 Not Listed For Sale

      • 6 Beds
      • 4 Baths
      • 4,923 Sq Ft

      208 Ridge St, Winchester, MA 01890

      208 Ridge St, Winchester, MA 01890
    • 35 Squire Rd, Winchester, MA 01890
      35 Squire Rd, Winchester, MA 01890
      35 Squire Rd, Winchester, MA 01890
      /8

      Est $2,234,546 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,860 Sq Ft

      35 Squire Rd, Winchester, MA 01890

      35 Squire Rd, Winchester, MA 01890
    • 21 Squire Rd, Winchester, MA 01890
      21 Squire Rd, Winchester, MA 01890
      21 Squire Rd, Winchester, MA 01890
      /38

      Est $1,408,084 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,704 Sq Ft

      21 Squire Rd, Winchester, MA 01890

      21 Squire Rd, Winchester, MA 01890
    • 17 Squire Rd, Winchester, MA 01890
      17 Squire Rd, Winchester, MA 01890
      17 Squire Rd, Winchester, MA 01890
      /41

      Est $1,366,067 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,364 Sq Ft

      17 Squire Rd, Winchester, MA 01890

      17 Squire Rd, Winchester, MA 01890
    • 9 Squire Rd, Winchester, MA 01890
      9 Squire Rd, Winchester, MA 01890
      9 Squire Rd, Winchester, MA 01890
      /39

      Est $1,598,181 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 2,750 Sq Ft

      9 Squire Rd, Winchester, MA 01890

      9 Squire Rd, Winchester, MA 01890
    • 12 Carriage Ln, Winchester, MA 01890
      12 Carriage Ln, Winchester, MA 01890
      12 Carriage Ln, Winchester, MA 01890
      /31

      Est $1,175,145 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,856 Sq Ft

      12 Carriage Ln, Winchester, MA 01890

      12 Carriage Ln, Winchester, MA 01890
    • 16 Thornberry Rd, Winchester, MA 01890
      16 Thornberry Rd, Winchester, MA 01890
      16 Thornberry Rd, Winchester, MA 01890
      /42

      Est $1,536,372 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,530 Sq Ft

      16 Thornberry Rd, Winchester, MA 01890

      16 Thornberry Rd, Winchester, MA 01890
    • 29 Thornberry Rd, Winchester, MA 01890
      29 Thornberry Rd, Winchester, MA 01890
      29 Thornberry Rd, Winchester, MA 01890
      /20

      Est $1,385,392 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,700 Sq Ft

      29 Thornberry Rd, Winchester, MA 01890

      29 Thornberry Rd, Winchester, MA 01890
    • 49 Thornberry Rd, Winchester, MA 01890
      49 Thornberry Rd, Winchester, MA 01890
      49 Thornberry Rd, Winchester, MA 01890
      /8

      Est $1,673,837 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,600 Sq Ft

      49 Thornberry Rd, Winchester, MA 01890

      49 Thornberry Rd, Winchester, MA 01890
    • 57 Thornberry Rd, Winchester, MA 01890
      57 Thornberry Rd, Winchester, MA 01890
      57 Thornberry Rd, Winchester, MA 01890
      /42

      Est $2,283,141 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 4,074 Sq Ft

      57 Thornberry Rd, Winchester, MA 01890

      57 Thornberry Rd, Winchester, MA 01890
    • 259 High St, Winchester, MA 01890
      259 High St, Winchester, MA 01890
      259 High St, Winchester, MA 01890
      /42

      Est $2,878,341 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 4,412 Sq Ft

      259 High St, Winchester, MA 01890

      259 High St, Winchester, MA 01890
    • 94 Thornberry Rd, Winchester, MA 01890
      94 Thornberry Rd, Winchester, MA 01890
      94 Thornberry Rd, Winchester, MA 01890
      /29

      Est $1,670,429 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,043 Sq Ft

      94 Thornberry Rd, Winchester, MA 01890

      94 Thornberry Rd, Winchester, MA 01890
    • 98 Thornberry Rd, Winchester, MA 01890
      98 Thornberry Rd, Winchester, MA 01890
      98 Thornberry Rd, Winchester, MA 01890
      /20

      Est $1,548,129 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 2,983 Sq Ft

      98 Thornberry Rd, Winchester, MA 01890

      98 Thornberry Rd, Winchester, MA 01890
    • 103 Thornberry Rd, Winchester, MA 01890
      103 Thornberry Rd, Winchester, MA 01890
      103 Thornberry Rd, Winchester, MA 01890
      /42

      Est $1,610,133 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,246 Sq Ft

      103 Thornberry Rd, Winchester, MA 01890

      103 Thornberry Rd, Winchester, MA 01890
    • 67 Thornberry Rd, Winchester, MA 01890
      67 Thornberry Rd, Winchester, MA 01890
      67 Thornberry Rd, Winchester, MA 01890
      /30

      Est $1,907,458 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,337 Sq Ft

      67 Thornberry Rd, Winchester, MA 01890

      67 Thornberry Rd, Winchester, MA 01890
    • 75 Thornberry Rd, Winchester, MA 01890
      75 Thornberry Rd, Winchester, MA 01890
      75 Thornberry Rd, Winchester, MA 01890
      /41

      Est $2,389,698 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 4,462 Sq Ft

      75 Thornberry Rd, Winchester, MA 01890

      75 Thornberry Rd, Winchester, MA 01890
    • 18 Berkshire Dr, Winchester, MA 01890
      18 Berkshire Dr, Winchester, MA 01890
      18 Berkshire Dr, Winchester, MA 01890
      /29

      Est $1,718,486 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,626 Sq Ft

      18 Berkshire Dr, Winchester, MA 01890

      18 Berkshire Dr, Winchester, MA 01890
    • 3 Partridge Ln, Winchester, MA 01890
      3 Partridge Ln, Winchester, MA 01890
      3 Partridge Ln, Winchester, MA 01890
      /22

      Est $1,761,946 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,175 Sq Ft

      3 Partridge Ln, Winchester, MA 01890

      3 Partridge Ln, Winchester, MA 01890
    • 90 Thornberry Rd, Winchester, MA 01890
      90 Thornberry Rd, Winchester, MA 01890
      90 Thornberry Rd, Winchester, MA 01890
      /42

      Est $1,829,292 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 3,082 Sq Ft

      90 Thornberry Rd, Winchester, MA 01890

      90 Thornberry Rd, Winchester, MA 01890
    • 2 Berkshire Dr, Winchester, MA 01890
      2 Berkshire Dr, Winchester, MA 01890
      2 Berkshire Dr, Winchester, MA 01890
      /42

      Est $1,452,951 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,650 Sq Ft

      2 Berkshire Dr, Winchester, MA 01890

      2 Berkshire Dr, Winchester, MA 01890
    • 119 Johnson Rd, Winchester, MA 01890
      119 Johnson Rd, Winchester, MA 01890
      119 Johnson Rd, Winchester, MA 01890
      /12

      Est $2,550,330 Not Listed For Sale

      • 6 Beds
      • 6 Baths
      • 4,600 Sq Ft

      119 Johnson Rd, Winchester, MA 01890

      119 Johnson Rd, Winchester, MA 01890

Showing Results 161 - 200, Page 5 of 18

Massachusetts 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.

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