1,482

Winchester Highlands Homes

Section Image
    • 20 Kenwin Rd, Winchester, MA 01890
      20 Kenwin Rd, Winchester, MA 01890
      20 Kenwin Rd, Winchester, MA 01890
      /39

      Est $1,478,240 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,209 Sq Ft

      20 Kenwin Rd, Winchester, MA 01890

      20 Kenwin Rd, Winchester, MA 01890
    • 10 Grayson Rd, Winchester, MA 01890
      10 Grayson Rd, Winchester, MA 01890
      10 Grayson Rd, Winchester, MA 01890
      /40

      Est $1,619,525 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,316 Sq Ft

      10 Grayson Rd, Winchester, MA 01890

      10 Grayson Rd, Winchester, MA 01890
    • 457 Washington St, Winchester, MA 01890
      457 Washington St, Winchester, MA 01890
      457 Washington St, Winchester, MA 01890
      /23

      Est $977,647 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,494 Sq Ft

      457 Washington St, Winchester, MA 01890

      457 Washington St, Winchester, MA 01890
    • 12 Bonad Rd, Winchester, MA 01890
      12 Bonad Rd, Winchester, MA 01890
      12 Bonad Rd, Winchester, MA 01890
      /36

      Est $1,876,286 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,899 Sq Ft

      12 Bonad Rd, Winchester, MA 01890

      12 Bonad Rd, Winchester, MA 01890
    • 18 Bonad Rd, Winchester, MA 01890
      18 Bonad Rd, Winchester, MA 01890
      18 Bonad Rd, Winchester, MA 01890
      /28

      Est $1,237,391 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,450 Sq Ft

      18 Bonad Rd, Winchester, MA 01890

      18 Bonad Rd, Winchester, MA 01890
    • 40 Englewood Rd, Winchester, MA 01890
      40 Englewood Rd, Winchester, MA 01890
      40 Englewood Rd, Winchester, MA 01890
      /31

      Est $1,241,487 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,459 Sq Ft

      40 Englewood Rd, Winchester, MA 01890

      40 Englewood Rd, Winchester, MA 01890
    • 93 Highland Ave, Winchester, MA 01890
      93 Highland Ave, Winchester, MA 01890
      93 Highland Ave, Winchester, MA 01890
      /42

      Est $1,387,738 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,508 Sq Ft

      93 Highland Ave, Winchester, MA 01890

      93 Highland Ave, Winchester, MA 01890
    • 21 Grayson Rd, Winchester, MA 01890
      21 Grayson Rd, Winchester, MA 01890
      21 Grayson Rd, Winchester, MA 01890
      /32

      Est $1,649,935 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,007 Sq Ft

      21 Grayson Rd, Winchester, MA 01890

      21 Grayson Rd, Winchester, MA 01890
    • 3 Bonad Rd, Winchester, MA 01890
      3 Bonad Rd, Winchester, MA 01890
      3 Bonad Rd, Winchester, MA 01890
      /21

      Est $1,418,954 Not Listed For Sale

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

      3 Bonad Rd, Winchester, MA 01890

      3 Bonad Rd, Winchester, MA 01890
    • 11 Bonad Rd, Winchester, MA 01890
      11 Bonad Rd, Winchester, MA 01890
      11 Bonad Rd, Winchester, MA 01890
      /36

      Est $1,988,578 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,169 Sq Ft

      11 Bonad Rd, Winchester, MA 01890

      11 Bonad Rd, Winchester, MA 01890
    • 3 Churchill Cir, Winchester, MA 01890
      3 Churchill Cir, Winchester, MA 01890
      3 Churchill Cir, Winchester, MA 01890
      /42

      Est $2,617,902 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 4,436 Sq Ft

      3 Churchill Cir, Winchester, MA 01890

      3 Churchill Cir, Winchester, MA 01890
    • 73 Sunset Rd, Winchester, MA 01890
      73 Sunset Rd, Winchester, MA 01890
      73 Sunset Rd, Winchester, MA 01890
      /42

      Est $2,853,060 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 5,523 Sq Ft

      73 Sunset Rd, Winchester, MA 01890

      73 Sunset Rd, Winchester, MA 01890
    • 3 Sunset Rd, Winchester, MA 01890
      3 Sunset Rd, Winchester, MA 01890
      3 Sunset Rd, Winchester, MA 01890
      /42

      Est $1,688,023 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,736 Sq Ft

      3 Sunset Rd, Winchester, MA 01890

      3 Sunset Rd, Winchester, MA 01890
    • 76 N Border Rd, Winchester, MA 01890
      76 N Border Rd, Winchester, MA 01890
      76 N Border Rd, Winchester, MA 01890
      /22

      Est $1,661,728 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,854 Sq Ft

      76 N Border Rd, Winchester, MA 01890

      76 N Border Rd, Winchester, MA 01890
    • 15 Ware Rd, Winchester, MA 01890
      15 Ware Rd, Winchester, MA 01890
      15 Ware Rd, Winchester, MA 01890
      /40

      Est $1,288,885 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,977 Sq Ft

      15 Ware Rd, Winchester, MA 01890

      15 Ware Rd, Winchester, MA 01890
    • 5 Dean Rd, Winchester, MA 01890
      5 Dean Rd, Winchester, MA 01890
      5 Dean Rd, Winchester, MA 01890
      /42

      Est $2,822,336 Not Listed For Sale

      • 6 Beds
      • 5 Baths
      • 6,171 Sq Ft

      5 Dean Rd, Winchester, MA 01890

      5 Dean Rd, Winchester, MA 01890
    • 211 Forest St, Winchester, MA 01890
      211 Forest St, Winchester, MA 01890
      211 Forest St, Winchester, MA 01890
      /41

      Est $1,954,160 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,474 Sq Ft

      211 Forest St, Winchester, MA 01890

      211 Forest St, Winchester, MA 01890
    • 35 Forest Cir, Winchester, MA 01890
      35 Forest Cir, Winchester, MA 01890
      35 Forest Cir, Winchester, MA 01890
      /39

      Est $1,510,383 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,618 Sq Ft

      35 Forest Cir, Winchester, MA 01890

      35 Forest Cir, Winchester, MA 01890
    • 11 Bellevue Ave, Winchester, MA 01890
      11 Bellevue Ave, Winchester, MA 01890
      11 Bellevue Ave, Winchester, MA 01890
      /33

      Est $2,529,671 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 5,731 Sq Ft

      11 Bellevue Ave, Winchester, MA 01890

      11 Bellevue Ave, Winchester, MA 01890
    • 4 Bellevue Ave, Winchester, MA 01890
      4 Bellevue Ave, Winchester, MA 01890
      4 Bellevue Ave, Winchester, MA 01890
      /42

      Est $1,514,963 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,900 Sq Ft

      4 Bellevue Ave, Winchester, MA 01890

      4 Bellevue Ave, Winchester, MA 01890
    • 21 Laurel Hill Ln, Winchester, MA 01890
      21 Laurel Hill Ln, Winchester, MA 01890
      21 Laurel Hill Ln, Winchester, MA 01890
      /30

      Est $3,063,295 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 5,600 Sq Ft

      21 Laurel Hill Ln, Winchester, MA 01890

      21 Laurel Hill Ln, Winchester, MA 01890
    • 5 Grant Rd, Winchester, MA 01890
      5 Grant Rd, Winchester, MA 01890
      5 Grant Rd, Winchester, MA 01890
      /24

      Est $1,798,968 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,592 Sq Ft

      5 Grant Rd, Winchester, MA 01890

      5 Grant Rd, Winchester, MA 01890
    • 4 Hinds Rd, Winchester, MA 01890
      4 Hinds Rd, Winchester, MA 01890
      4 Hinds Rd, Winchester, MA 01890
      /37

      Est $1,237,766 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,970 Sq Ft

      4 Hinds Rd, Winchester, MA 01890

      4 Hinds Rd, Winchester, MA 01890
    • 8 Sunset Rd, Winchester, MA 01890
      8 Sunset Rd, Winchester, MA 01890
      8 Sunset Rd, Winchester, MA 01890
      /42

      Est $1,599,709 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,029 Sq Ft

      8 Sunset Rd, Winchester, MA 01890

      8 Sunset Rd, Winchester, MA 01890
    • 148 Forest St, Winchester, MA 01890
      148 Forest St, Winchester, MA 01890
      148 Forest St, Winchester, MA 01890
      /38

      Est $1,954,233 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 4,225 Sq Ft

      148 Forest St, Winchester, MA 01890

      148 Forest St, Winchester, MA 01890
    • 525 Washington St Unit 525, Winchester, MA 01890
      525 Washington St Unit 525, Winchester, MA 01890
      525 Washington St Unit 525, Winchester, MA 01890
      /31

      Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,119 Sq Ft

      525 Washington St Unit 525, Winchester, MA 01890

      525 Washington St Unit 525, Winchester, MA 01890
    • 87 Harvard St Unit 87, Winchester, MA 01890
      87 Harvard St Unit 87, Winchester, MA 01890
      87 Harvard St Unit 87, Winchester, MA 01890
      /38

      Est $1,085,853 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,280 Sq Ft

      87 Harvard St Unit 87, Winchester, MA 01890

      87 Harvard St Unit 87, Winchester, MA 01890
    • 31 Irving St Unit 31, Winchester, MA 01890
      31 Irving St Unit 31, Winchester, MA 01890
      31 Irving St Unit 31, Winchester, MA 01890
      /23

      Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,262 Sq Ft

      31 Irving St Unit 31, Winchester, MA 01890

      31 Irving St Unit 31, Winchester, MA 01890
    • 2 Grayson Rd Unit 2, Winchester, MA 01890
      2 Grayson Rd Unit 2, Winchester, MA 01890
      2 Grayson Rd Unit 2, Winchester, MA 01890
      /36

      Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,446 Sq Ft

      2 Grayson Rd Unit 2, Winchester, MA 01890

      2 Grayson Rd Unit 2, Winchester, MA 01890
    • 252 Forest St, Winchester, MA 01890
      252 Forest St, Winchester, MA 01890
      252 Forest St, Winchester, MA 01890
      /6

      Est $2,377,115 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 4,208 Sq Ft

      252 Forest St, Winchester, MA 01890

      252 Forest St, Winchester, MA 01890
    • 256 Forest St, Winchester, MA 01890
      256 Forest St, Winchester, MA 01890
      256 Forest St, Winchester, MA 01890
      /42

      Est $2,352,105 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 4,334 Sq Ft

      256 Forest St, Winchester, MA 01890

      256 Forest St, Winchester, MA 01890
    • 248 Forest St, Winchester, MA 01890
      248 Forest St, Winchester, MA 01890
      248 Forest St, Winchester, MA 01890
      /42

      Est $2,566,397 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 5,200 Sq Ft

      248 Forest St, Winchester, MA 01890

      248 Forest St, Winchester, MA 01890
    • 37 Swanton St Unit 1, Winchester, MA 01890
      37 Swanton St Unit 1, Winchester, MA 01890
      37 Swanton St Unit 1, Winchester, MA 01890
      /34

      Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,272 Sq Ft

      37 Swanton St Unit 1, Winchester, MA 01890

      37 Swanton St Unit 1, Winchester, MA 01890
    • 15 Governors Ave Unit 1, Winchester, MA 01890
      15 Governors Ave Unit 1, Winchester, MA 01890
      15 Governors Ave Unit 1, Winchester, MA 01890
      /27

      Est $719,560 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,300 Sq Ft

      15 Governors Ave Unit 1, Winchester, MA 01890

      15 Governors Ave Unit 1, Winchester, MA 01890
    • 34 Irving St Unit 1, Winchester, MA 01890
      34 Irving St Unit 1, Winchester, MA 01890
      /2

      Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 600 Sq Ft

      34 Irving St Unit 1, Winchester, MA 01890

      34 Irving St Unit 1, Winchester, MA 01890
    • 60 Sunset Rd, Winchester, MA 01890
      60 Sunset Rd, Winchester, MA 01890
      60 Sunset Rd, Winchester, MA 01890
      /27

      Est $2,420,901 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 3,973 Sq Ft

      60 Sunset Rd, Winchester, MA 01890

      60 Sunset Rd, Winchester, MA 01890
    • 21 Brookside Ave, Winchester, MA 01890
      21 Brookside Ave, Winchester, MA 01890
      21 Brookside Ave, Winchester, MA 01890
      /15

      Est $791,614 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,566 Sq Ft

      21 Brookside Ave, Winchester, MA 01890

      21 Brookside Ave, Winchester, MA 01890
    • 14 Park Ave Unit 2, Winchester, MA 01890
      14 Park Ave Unit 2, Winchester, MA 01890
      14 Park Ave Unit 2, Winchester, MA 01890
      /20

      Est $944,896 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,861 Sq Ft

      14 Park Ave Unit 2, Winchester, MA 01890

      14 Park Ave Unit 2, Winchester, MA 01890
    • 8 Bates Rd Unit 1, Winchester, MA 01890
      8 Bates Rd Unit 1, Winchester, MA 01890
      8 Bates Rd Unit 1, Winchester, MA 01890
      /30

      Est $1,536,559 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 2,971 Sq Ft

      8 Bates Rd Unit 1, Winchester, MA 01890

      8 Bates Rd Unit 1, Winchester, MA 01890
    • 11 Tufts Rd Unit 11, Winchester, MA 01890
      11 Tufts Rd Unit 11, Winchester, MA 01890
      /2

      Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,230 Sq Ft

      11 Tufts Rd Unit 11, Winchester, MA 01890

      11 Tufts Rd Unit 11, Winchester, MA 01890

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