1,482

Winchester Highlands Homes

Section Image
    • 26 Forest St, Winchester, MA 01890
      26 Forest St, Winchester, MA 01890
      26 Forest St, Winchester, MA 01890
      /30

      Est $1,356,220 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,325 Sq Ft

      26 Forest St, Winchester, MA 01890

      26 Forest St, Winchester, MA 01890
    • 21 Forest St, Winchester, MA 01890
      21 Forest St, Winchester, MA 01890
      21 Forest St, Winchester, MA 01890
      /42

      Est $891,893 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,120 Sq Ft

      21 Forest St, Winchester, MA 01890

      21 Forest St, Winchester, MA 01890
    • 15 Nathaniel Rd, Winchester, MA 01890
      15 Nathaniel Rd, Winchester, MA 01890
      15 Nathaniel Rd, Winchester, MA 01890
      /35

      Est $1,614,574 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,115 Sq Ft

      15 Nathaniel Rd, Winchester, MA 01890

      15 Nathaniel Rd, Winchester, MA 01890
    • 35 Nathaniel Rd, Winchester, MA 01890
      35 Nathaniel Rd, Winchester, MA 01890
      35 Nathaniel Rd, Winchester, MA 01890
      /41

      Est $1,384,841 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,583 Sq Ft

      35 Nathaniel Rd, Winchester, MA 01890

      35 Nathaniel Rd, Winchester, MA 01890
    • 434 Washington St Unit 436, Winchester, MA 01890
      434 Washington St Unit 436, Winchester, MA 01890
      434 Washington St Unit 436, Winchester, MA 01890
      /39

      Est $1,101,359 Not Listed For Sale

      • 6 Beds
      • 4 Baths
      • 2,230 Sq Ft

      434 Washington St Unit 436, Winchester, MA 01890

      434 Washington St Unit 436, Winchester, MA 01890
    • 5 Tufts Rd, Winchester, MA 01890
      5 Tufts Rd, Winchester, MA 01890
      5 Tufts Rd, Winchester, MA 01890
      /40

      Est $1,356,155 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,492 Sq Ft

      5 Tufts Rd, Winchester, MA 01890

      5 Tufts Rd, Winchester, MA 01890
    • 43 Nathaniel Rd, Winchester, MA 01890
      43 Nathaniel Rd, Winchester, MA 01890
      43 Nathaniel Rd, Winchester, MA 01890
      /41

      Est $1,325,324 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,009 Sq Ft

      43 Nathaniel Rd, Winchester, MA 01890

      43 Nathaniel Rd, Winchester, MA 01890
    • 22 Tufts Rd, Winchester, MA 01890
      22 Tufts Rd, Winchester, MA 01890
      22 Tufts Rd, Winchester, MA 01890
      /29

      Est $1,251,097 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,716 Sq Ft

      22 Tufts Rd, Winchester, MA 01890

      22 Tufts Rd, Winchester, MA 01890
    • 41 Irving St, Winchester, MA 01890
      41 Irving St, Winchester, MA 01890
      41 Irving St, Winchester, MA 01890
      /25

      Est $1,124,895 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,633 Sq Ft

      41 Irving St, Winchester, MA 01890

      41 Irving St, Winchester, MA 01890
    • 74 Chester St, Winchester, MA 01890
      74 Chester St, Winchester, MA 01890
      74 Chester St, Winchester, MA 01890
      /34

      Est $1,228,202 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,880 Sq Ft

      74 Chester St, Winchester, MA 01890

      74 Chester St, Winchester, MA 01890
    • 15 Chester St, Winchester, MA 01890
      15 Chester St, Winchester, MA 01890
      15 Chester St, Winchester, MA 01890
      /27

      Est $1,514,886 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,371 Sq Ft

      15 Chester St, Winchester, MA 01890

      15 Chester St, Winchester, MA 01890
    • 49 Florence St, Winchester, MA 01890
      49 Florence St, Winchester, MA 01890
      49 Florence St, Winchester, MA 01890
      /22

      Est $1,831,055 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,742 Sq Ft

      49 Florence St, Winchester, MA 01890

      49 Florence St, Winchester, MA 01890
    • 36 Chester St, Winchester, MA 01890
      36 Chester St, Winchester, MA 01890
      36 Chester St, Winchester, MA 01890
      /6

      Est $2,134,699 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 4,078 Sq Ft

      36 Chester St, Winchester, MA 01890

      36 Chester St, Winchester, MA 01890
    • 66 Irving St, Winchester, MA 01890
      66 Irving St, Winchester, MA 01890
      66 Irving St, Winchester, MA 01890
      /19

      Est $1,105,450 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,585 Sq Ft

      66 Irving St, Winchester, MA 01890

      66 Irving St, Winchester, MA 01890
    • 22 Olive St, Winchester, MA 01890
      22 Olive St, Winchester, MA 01890
      22 Olive St, Winchester, MA 01890
      /35

      Est $1,225,421 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,464 Sq Ft

      22 Olive St, Winchester, MA 01890

      22 Olive St, Winchester, MA 01890
    • 309 Washington St, Winchester, MA 01890
      309 Washington St, Winchester, MA 01890
      309 Washington St, Winchester, MA 01890
      /37

      Est $997,401 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,325 Sq Ft

      309 Washington St, Winchester, MA 01890

      309 Washington St, Winchester, MA 01890
    • 28 Fells Rd, Winchester, MA 01890
      28 Fells Rd, Winchester, MA 01890
      28 Fells Rd, Winchester, MA 01890
      /42

      Est $3,224,726 Not Listed For Sale

      • 6 Beds
      • 7 Baths
      • 6,033 Sq Ft

      28 Fells Rd, Winchester, MA 01890

      28 Fells Rd, Winchester, MA 01890
    • 124 Highland Ave, Winchester, MA 01890
      124 Highland Ave, Winchester, MA 01890
      124 Highland Ave, Winchester, MA 01890
      /42

      Est $2,363,777 Not Listed For Sale

      • 6 Beds
      • 4 Baths
      • 3,422 Sq Ft

      124 Highland Ave, Winchester, MA 01890

      124 Highland Ave, Winchester, MA 01890
    • 3 Wilson St, Winchester, MA 01890
      3 Wilson St, Winchester, MA 01890
      3 Wilson St, Winchester, MA 01890
      /35

      Est $1,750,276 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,308 Sq Ft

      3 Wilson St, Winchester, MA 01890

      3 Wilson St, Winchester, MA 01890
    • 423 Washington St, Winchester, MA 01890
      423 Washington St, Winchester, MA 01890
      423 Washington St, Winchester, MA 01890
      /37

      Est $1,438,748 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,560 Sq Ft

      423 Washington St, Winchester, MA 01890

      423 Washington St, Winchester, MA 01890
    • 9 Englewood Rd, Winchester, MA 01890
      9 Englewood Rd, Winchester, MA 01890
      9 Englewood Rd, Winchester, MA 01890
      /21

      Est $1,523,177 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,936 Sq Ft

      9 Englewood Rd, Winchester, MA 01890

      9 Englewood Rd, Winchester, MA 01890
    • 31 Englewood Rd, Winchester, MA 01890
      31 Englewood Rd, Winchester, MA 01890
      31 Englewood Rd, Winchester, MA 01890
      /32

      Est $1,486,414 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,438 Sq Ft

      31 Englewood Rd, Winchester, MA 01890

      31 Englewood Rd, Winchester, MA 01890
    • 101 Highland Ave, Winchester, MA 01890
      101 Highland Ave, Winchester, MA 01890
      101 Highland Ave, Winchester, MA 01890
      /28

      Est $1,621,957 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,514 Sq Ft

      101 Highland Ave, Winchester, MA 01890

      101 Highland Ave, Winchester, MA 01890
    • 6 Stone Ave, Winchester, MA 01890
      6 Stone Ave, Winchester, MA 01890
      6 Stone Ave, Winchester, MA 01890
      /26

      Est $1,213,694 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,890 Sq Ft

      6 Stone Ave, Winchester, MA 01890

      6 Stone Ave, Winchester, MA 01890
    • 12 Prince Ave, Winchester, MA 01890
      12 Prince Ave, Winchester, MA 01890
      12 Prince Ave, Winchester, MA 01890
      /27

      Est $1,383,582 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 2,725 Sq Ft

      12 Prince Ave, Winchester, MA 01890

      12 Prince Ave, Winchester, MA 01890
    • 4 Prince Ave, Winchester, MA 01890
      4 Prince Ave, Winchester, MA 01890
      4 Prince Ave, Winchester, MA 01890
      /28

      Est $1,453,914 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,680 Sq Ft

      4 Prince Ave, Winchester, MA 01890

      4 Prince Ave, Winchester, MA 01890
    • 157 Highland Ave, Winchester, MA 01890
      157 Highland Ave, Winchester, MA 01890
      157 Highland Ave, Winchester, MA 01890
      /41

      Est $1,986,783 Not Listed For Sale

      • 6 Beds
      • 4 Baths
      • 3,839 Sq Ft

      157 Highland Ave, Winchester, MA 01890

      157 Highland Ave, Winchester, MA 01890
    • 64 Highland Ave Unit 15, Winchester, MA 01890
      64 Highland Ave Unit 15, Winchester, MA 01890
      64 Highland Ave Unit 15, Winchester, MA 01890
      /24

      Est $521,044 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 840 Sq Ft

      64 Highland Ave Unit 15, Winchester, MA 01890

      64 Highland Ave Unit 15, Winchester, MA 01890
    • 64 Highland Ave Unit 14, Winchester, MA 01890
      64 Highland Ave Unit 14, Winchester, MA 01890
      64 Highland Ave Unit 14, Winchester, MA 01890
      /37

      Est $944,726 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 3,101 Sq Ft

      64 Highland Ave Unit 14, Winchester, MA 01890

      64 Highland Ave Unit 14, Winchester, MA 01890
    • 64 Highland Ave Unit 2, Winchester, MA 01890
      64 Highland Ave Unit 2, Winchester, MA 01890
      64 Highland Ave Unit 2, Winchester, MA 01890
      /21

      Est $755,281 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,712 Sq Ft

      64 Highland Ave Unit 2, Winchester, MA 01890

      64 Highland Ave Unit 2, Winchester, MA 01890
    • 64 Highland Ave Unit 1, Winchester, MA 01890
      64 Highland Ave Unit 1, Winchester, MA 01890
      64 Highland Ave Unit 1, Winchester, MA 01890
      /28

      Est $731,938 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,610 Sq Ft

      64 Highland Ave Unit 1, Winchester, MA 01890

      64 Highland Ave Unit 1, Winchester, MA 01890
    • 35 Grayson Rd, Winchester, MA 01890
      35 Grayson Rd, Winchester, MA 01890
      35 Grayson Rd, Winchester, MA 01890
      /22

      Est $1,309,698 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 2,289 Sq Ft

      35 Grayson Rd, Winchester, MA 01890

      35 Grayson Rd, Winchester, MA 01890
    • 34 N Border Rd, Winchester, MA 01890
      34 N Border Rd, Winchester, MA 01890
      34 N Border Rd, Winchester, MA 01890
      /40

      Est $1,714,124 Not Listed For Sale

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

      34 N Border Rd, Winchester, MA 01890

      34 N Border Rd, Winchester, MA 01890
    • 2 Maple Rd, Winchester, MA 01890
      2 Maple Rd, Winchester, MA 01890
      2 Maple Rd, Winchester, MA 01890
      /40

      Est $2,343,264 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 4,030 Sq Ft

      2 Maple Rd, Winchester, MA 01890

      2 Maple Rd, Winchester, MA 01890
    • 7 Maple Rd, Winchester, MA 01890
      7 Maple Rd, Winchester, MA 01890
      7 Maple Rd, Winchester, MA 01890
      /38

      Est $2,056,781 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,778 Sq Ft

      7 Maple Rd, Winchester, MA 01890

      7 Maple Rd, Winchester, MA 01890
    • 119 Forest St, Winchester, MA 01890
      119 Forest St, Winchester, MA 01890
      119 Forest St, Winchester, MA 01890
      /41

      Est $2,556,424 Not Listed For Sale

      • 5 Beds
      • 6 Baths
      • 6,635 Sq Ft

      119 Forest St, Winchester, MA 01890

      119 Forest St, Winchester, MA 01890
    • 5 Orient St, Winchester, MA 01890
      5 Orient St, Winchester, MA 01890
      5 Orient St, Winchester, MA 01890
      /42

      Est $1,645,620 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,178 Sq Ft

      5 Orient St, Winchester, MA 01890

      5 Orient St, Winchester, MA 01890
    • 65 Highland Ave, Winchester, MA 01890
      65 Highland Ave, Winchester, MA 01890
      65 Highland Ave, Winchester, MA 01890
      /28

      Est $1,815,921 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,107 Sq Ft

      65 Highland Ave, Winchester, MA 01890

      65 Highland Ave, Winchester, MA 01890
    • 30 Kenwin Rd, Winchester, MA 01890
      30 Kenwin Rd, Winchester, MA 01890
      30 Kenwin Rd, Winchester, MA 01890
      /40

      Est $1,370,183 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,100 Sq Ft

      30 Kenwin Rd, Winchester, MA 01890

      30 Kenwin Rd, Winchester, MA 01890
    • 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

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