1,483

Winchester Highlands Homes

Section Image
    • 39 Swanton St, Winchester, MA 01890
      39 Swanton St, Winchester, MA 01890
      39 Swanton St, Winchester, MA 01890
      /5

      Est $853,671 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,780 Sq Ft

      39 Swanton St, Winchester, MA 01890

      39 Swanton St, Winchester, MA 01890
    • 33 Irving St, Winchester, MA 01890
      33 Irving St, Winchester, MA 01890
      33 Irving St, Winchester, MA 01890
      /16

      Est $765,349 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,227 Sq Ft

      33 Irving St, Winchester, MA 01890

      33 Irving St, Winchester, MA 01890
    • 43 Chester St Unit A, Winchester, MA 01890
      43 Chester St Unit A, Winchester, MA 01890
      /2

      Est $1,234,316 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,816 Sq Ft

      43 Chester St Unit A, Winchester, MA 01890

      43 Chester St Unit A, Winchester, MA 01890
    • 488 Washington St, Winchester, MA 01890
      488 Washington St, Winchester, MA 01890
      488 Washington St, Winchester, MA 01890
      /29

      Est $1,042,634 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 1,630 Sq Ft

      488 Washington St, Winchester, MA 01890

      488 Washington St, Winchester, MA 01890
    • 23 Nathaniel Rd, Winchester, MA 01890
      23 Nathaniel Rd, Winchester, MA 01890
      23 Nathaniel Rd, Winchester, MA 01890
      /22

      Est $1,278,060 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,003 Sq Ft

      23 Nathaniel Rd, Winchester, MA 01890

      23 Nathaniel Rd, Winchester, MA 01890
    • 29 Nathaniel Rd, Winchester, MA 01890
      29 Nathaniel Rd, Winchester, MA 01890
      29 Nathaniel Rd, Winchester, MA 01890
      /29

      Est $1,368,940 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,349 Sq Ft

      29 Nathaniel Rd, Winchester, MA 01890

      29 Nathaniel Rd, Winchester, MA 01890
    • 36 Nathaniel Rd, Winchester, MA 01890
      36 Nathaniel Rd, Winchester, MA 01890
      36 Nathaniel Rd, Winchester, MA 01890
      /18

      Est $1,291,716 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,074 Sq Ft

      36 Nathaniel Rd, Winchester, MA 01890

      36 Nathaniel Rd, Winchester, MA 01890
    • 18 Nathaniel Rd, Winchester, MA 01890
      18 Nathaniel Rd, Winchester, MA 01890
      18 Nathaniel Rd, Winchester, MA 01890
      /29

      Est $1,246,777 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,187 Sq Ft

      18 Nathaniel Rd, Winchester, MA 01890

      18 Nathaniel Rd, Winchester, MA 01890
    • 16 Nathaniel Rd, Winchester, MA 01890
      16 Nathaniel Rd, Winchester, MA 01890
      16 Nathaniel Rd, Winchester, MA 01890
      /30

      Est $1,288,572 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,754 Sq Ft

      16 Nathaniel Rd, Winchester, MA 01890

      16 Nathaniel Rd, Winchester, MA 01890
    • 35 Tufts Rd, Winchester, MA 01890
      35 Tufts Rd, Winchester, MA 01890
      35 Tufts Rd, Winchester, MA 01890
      /18

      Est $1,134,049 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,650 Sq Ft

      35 Tufts Rd, Winchester, MA 01890

      35 Tufts Rd, Winchester, MA 01890
    • 20 Tufts Rd, Winchester, MA 01890
      20 Tufts Rd, Winchester, MA 01890
      20 Tufts Rd, Winchester, MA 01890
      /26

      Est $1,411,984 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,574 Sq Ft

      20 Tufts Rd, Winchester, MA 01890

      20 Tufts Rd, Winchester, MA 01890
    • 16 Tufts Rd, Winchester, MA 01890
      16 Tufts Rd, Winchester, MA 01890
      16 Tufts Rd, Winchester, MA 01890
      /22

      Est $1,444,754 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,644 Sq Ft

      16 Tufts Rd, Winchester, MA 01890

      16 Tufts Rd, Winchester, MA 01890
    • 398 Washington St, Winchester, MA 01890
      398 Washington St, Winchester, MA 01890
      398 Washington St, Winchester, MA 01890
      /6

      Est $1,250,462 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,196 Sq Ft

      398 Washington St, Winchester, MA 01890

      398 Washington St, Winchester, MA 01890
    • 7 Irving St, Winchester, MA 01890
      7 Irving St, Winchester, MA 01890
      7 Irving St, Winchester, MA 01890
      /23

      Est $1,565,433 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,669 Sq Ft

      7 Irving St, Winchester, MA 01890

      7 Irving St, Winchester, MA 01890
    • 43 Irving St Unit 45, Winchester, MA 01890
      43 Irving St Unit 45, Winchester, MA 01890
      43 Irving St Unit 45, Winchester, MA 01890
      /30

      Est $1,231,245 Not Listed For Sale

      • 6 Beds
      • 3 Baths
      • 3,019 Sq Ft

      43 Irving St Unit 45, Winchester, MA 01890

      43 Irving St Unit 45, Winchester, MA 01890
    • 77 Irving St, Winchester, MA 01890
      77 Irving St, Winchester, MA 01890
      77 Irving St, Winchester, MA 01890
      /12

      Est $1,909,723 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,000 Sq Ft

      77 Irving St, Winchester, MA 01890

      77 Irving St, Winchester, MA 01890
    • 69 Florence St, Winchester, MA 01890
      69 Florence St, Winchester, MA 01890
      69 Florence St, Winchester, MA 01890
      /20

      Est $1,280,364 Not Listed For Sale

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

      69 Florence St, Winchester, MA 01890

      69 Florence St, Winchester, MA 01890
    • 44 Irving St, Winchester, MA 01890
      44 Irving St, Winchester, MA 01890
      44 Irving St, Winchester, MA 01890
      /20

      Est $1,214,348 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,560 Sq Ft

      44 Irving St, Winchester, MA 01890

      44 Irving St, Winchester, MA 01890
    • 73 Chester St, Winchester, MA 01890
      73 Chester St, Winchester, MA 01890
      /2

      Est $1,184,466 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,938 Sq Ft

      73 Chester St, Winchester, MA 01890

      73 Chester St, Winchester, MA 01890
    • 8 Irving St, Winchester, MA 01890
      8 Irving St, Winchester, MA 01890
      8 Irving St, Winchester, MA 01890
      /12

      Est $1,230,627 Not Listed For Sale

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

      8 Irving St, Winchester, MA 01890

      8 Irving St, Winchester, MA 01890
    • 5 Harvard St, Winchester, MA 01890
      5 Harvard St, Winchester, MA 01890
      5 Harvard St, Winchester, MA 01890
      /29

      Est $1,118,060 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,769 Sq Ft

      5 Harvard St, Winchester, MA 01890

      5 Harvard St, Winchester, MA 01890
    • 33 Harvard St, Winchester, MA 01890
      33 Harvard St, Winchester, MA 01890
      33 Harvard St, Winchester, MA 01890
      /29

      Est $1,086,758 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,165 Sq Ft

      33 Harvard St, Winchester, MA 01890

      33 Harvard St, Winchester, MA 01890
    • 39 Harvard St, Winchester, MA 01890
      39 Harvard St, Winchester, MA 01890
      39 Harvard St, Winchester, MA 01890
      /16

      Est $1,314,757 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 3,087 Sq Ft

      39 Harvard St, Winchester, MA 01890

      39 Harvard St, Winchester, MA 01890
    • 47 Harvard St, Winchester, MA 01890
      47 Harvard St, Winchester, MA 01890
      47 Harvard St, Winchester, MA 01890
      /24

      Est $1,354,229 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 1,774 Sq Ft

      47 Harvard St, Winchester, MA 01890

      47 Harvard St, Winchester, MA 01890
    • 348 Washington St, Winchester, MA 01890
      348 Washington St, Winchester, MA 01890
      348 Washington St, Winchester, MA 01890
      /21

      Est $1,628,877 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 3,181 Sq Ft

      348 Washington St, Winchester, MA 01890

      348 Washington St, Winchester, MA 01890
    • 320 Washington St, Winchester, MA 01890
      320 Washington St, Winchester, MA 01890
      320 Washington St, Winchester, MA 01890
      /26

      Est $1,107,041 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,666 Sq Ft

      320 Washington St, Winchester, MA 01890

      320 Washington St, Winchester, MA 01890
    • 312 Washington St, Winchester, MA 01890
      312 Washington St, Winchester, MA 01890
      312 Washington St, Winchester, MA 01890
      /26

      Est $1,343,833 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,920 Sq Ft

      312 Washington St, Winchester, MA 01890

      312 Washington St, Winchester, MA 01890
    • 1 Chester St, Winchester, MA 01890
      1 Chester St, Winchester, MA 01890
      1 Chester St, Winchester, MA 01890
      /30

      Est $1,371,991 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,493 Sq Ft

      1 Chester St, Winchester, MA 01890

      1 Chester St, Winchester, MA 01890
    • 31 Chester St, Winchester, MA 01890
      31 Chester St, Winchester, MA 01890
      31 Chester St, Winchester, MA 01890
      /23

      Est $1,735,788 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,784 Sq Ft

      31 Chester St, Winchester, MA 01890

      31 Chester St, Winchester, MA 01890
    • 41 Chester St Unit 43, Winchester, MA 01890
      41 Chester St Unit 43, Winchester, MA 01890
      41 Chester St Unit 43, Winchester, MA 01890
      /14

      Est $689,519 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,456 Sq Ft

      41 Chester St Unit 43, Winchester, MA 01890

      41 Chester St Unit 43, Winchester, MA 01890
    • 3 Raymond Place, Winchester, MA 01890
      3 Raymond Place, Winchester, MA 01890
      3 Raymond Place, Winchester, MA 01890
      /23

      Est $1,614,020 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,944 Sq Ft

      3 Raymond Place, Winchester, MA 01890

      3 Raymond Place, Winchester, MA 01890
    • 18 Chester St, Winchester, MA 01890
      18 Chester St, Winchester, MA 01890
      18 Chester St, Winchester, MA 01890
      /29

      Est $1,788,788 Not Listed For Sale

      • 6 Beds
      • 4 Baths
      • 2,943 Sq Ft

      18 Chester St, Winchester, MA 01890

      18 Chester St, Winchester, MA 01890
    • 5 Emerson Ct, Winchester, MA 01890
      5 Emerson Ct, Winchester, MA 01890
      5 Emerson Ct, Winchester, MA 01890
      /25

      Est $1,341,880 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 2,200 Sq Ft

      5 Emerson Ct, Winchester, MA 01890

      5 Emerson Ct, Winchester, MA 01890
    • 49 Swanton St, Winchester, MA 01890
      49 Swanton St, Winchester, MA 01890
      49 Swanton St, Winchester, MA 01890
      /12

      Est $1,017,320 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,500 Sq Ft

      49 Swanton St, Winchester, MA 01890

      49 Swanton St, Winchester, MA 01890
    • 53 Swanton St Unit 55, Winchester, MA 01890
      53 Swanton St Unit 55, Winchester, MA 01890
      /2

      Est $1,164,246 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 950 Sq Ft

      53 Swanton St Unit 55, Winchester, MA 01890

      53 Swanton St Unit 55, Winchester, MA 01890
    • 17 Florence St, Winchester, MA 01890
      17 Florence St, Winchester, MA 01890
      17 Florence St, Winchester, MA 01890
      /23

      Est $1,312,702 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,912 Sq Ft

      17 Florence St, Winchester, MA 01890

      17 Florence St, Winchester, MA 01890
    • 5 Columbus Rd, Winchester, MA 01890
      5 Columbus Rd, Winchester, MA 01890
      5 Columbus Rd, Winchester, MA 01890
      /13

      Est $1,090,098 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 2,035 Sq Ft

      5 Columbus Rd, Winchester, MA 01890

      5 Columbus Rd, Winchester, MA 01890
    • 24 Raymond Place, Winchester, MA 01890
      24 Raymond Place, Winchester, MA 01890
      24 Raymond Place, Winchester, MA 01890
      /24

      Est $1,341,590 Not Listed For Sale

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

      24 Raymond Place, Winchester, MA 01890

      24 Raymond Place, Winchester, MA 01890
    • 35 Florence St Unit 37, Winchester, MA 01890
      35 Florence St Unit 37, Winchester, MA 01890
      /2

      Est $1,084,479 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 994 Sq Ft

      35 Florence St Unit 37, Winchester, MA 01890

      35 Florence St Unit 37, Winchester, MA 01890
    • 94 Irving St, Winchester, MA 01890
      94 Irving St, Winchester, MA 01890
      94 Irving St, Winchester, MA 01890
      /29

      Est $1,447,225 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,503 Sq Ft

      94 Irving St, Winchester, MA 01890

      94 Irving St, Winchester, MA 01890

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