1,483

Winchester Highlands Homes

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    • 64 Highland Ave Unit 6, Winchester, MA 01890
      64 Highland Ave Unit 6, Winchester, MA 01890
      64 Highland Ave Unit 6, Winchester, MA 01890
      /26

      Est $681,331 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,215 Sq Ft

      64 Highland Ave Unit 6, Winchester, MA 01890

      64 Highland Ave Unit 6, Winchester, MA 01890
    • 64 Highland Ave Unit 4, Winchester, MA 01890
      64 Highland Ave Unit 4, Winchester, MA 01890
      64 Highland Ave Unit 4, Winchester, MA 01890
      /12

      Est $454,367 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 782 Sq Ft

      64 Highland Ave Unit 4, Winchester, MA 01890

      64 Highland Ave Unit 4, Winchester, MA 01890
    • 6 Reservoir St, Winchester, MA 01890
      6 Reservoir St, Winchester, MA 01890
      6 Reservoir St, Winchester, MA 01890
      /20

      Est $1,311,804 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,382 Sq Ft

      6 Reservoir St, Winchester, MA 01890

      6 Reservoir St, Winchester, MA 01890
    • 7 Appalachian Rd, Winchester, MA 01890
      7 Appalachian Rd, Winchester, MA 01890
      7 Appalachian Rd, Winchester, MA 01890
      /18

      Est $1,963,172 Not Listed For Sale

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

      7 Appalachian Rd, Winchester, MA 01890

      7 Appalachian Rd, Winchester, MA 01890
    • 6 Hillcrest Pkwy, Winchester, MA 01890
      6 Hillcrest Pkwy, Winchester, MA 01890
      6 Hillcrest Pkwy, Winchester, MA 01890
      /30

      Est $1,955,862 Not Listed For Sale

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

      6 Hillcrest Pkwy, Winchester, MA 01890

      6 Hillcrest Pkwy, Winchester, MA 01890
    • 10 Hillcrest Pkwy, Winchester, MA 01890
      10 Hillcrest Pkwy, Winchester, MA 01890
      10 Hillcrest Pkwy, Winchester, MA 01890
      /30

      Est $1,898,774 Not Listed For Sale

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

      10 Hillcrest Pkwy, Winchester, MA 01890

      10 Hillcrest Pkwy, Winchester, MA 01890
    • 10 Fells Rd, Winchester, MA 01890
      10 Fells Rd, Winchester, MA 01890
      10 Fells Rd, Winchester, MA 01890
      /23

      Est $2,325,928 Not Listed For Sale

      • 6 Beds
      • 3 Baths
      • 3,122 Sq Ft

      10 Fells Rd, Winchester, MA 01890

      10 Fells Rd, Winchester, MA 01890
    • 94 Highland Ave, Winchester, MA 01890
      94 Highland Ave, Winchester, MA 01890
      94 Highland Ave, Winchester, MA 01890
      /30

      Est $2,487,755 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 4,343 Sq Ft

      94 Highland Ave, Winchester, MA 01890

      94 Highland Ave, Winchester, MA 01890
    • 8 Ainsworth Rd, Winchester, MA 01890
      8 Ainsworth Rd, Winchester, MA 01890
      8 Ainsworth Rd, Winchester, MA 01890
      /29

      Est $1,913,585 Not Listed For Sale

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

      8 Ainsworth Rd, Winchester, MA 01890

      8 Ainsworth Rd, Winchester, MA 01890
    • 2 Ainsworth Rd, Winchester, MA 01890
      2 Ainsworth Rd, Winchester, MA 01890
      2 Ainsworth Rd, Winchester, MA 01890
      /22

      Est $1,639,538 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,896 Sq Ft

      2 Ainsworth Rd, Winchester, MA 01890

      2 Ainsworth Rd, Winchester, MA 01890
    • 36 Highland Ave, Winchester, MA 01890
      36 Highland Ave, Winchester, MA 01890
      /2

      Est $1,092,809 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,601 Sq Ft

      36 Highland Ave, Winchester, MA 01890

      36 Highland Ave, Winchester, MA 01890
    • 11 Chisholm Rd, Winchester, MA 01890
      11 Chisholm Rd, Winchester, MA 01890
      11 Chisholm Rd, Winchester, MA 01890
      /29

      Est $1,483,975 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,048 Sq Ft

      11 Chisholm Rd, Winchester, MA 01890

      11 Chisholm Rd, Winchester, MA 01890
    • 2 Highland Ave, Winchester, MA 01890
      2 Highland Ave, Winchester, MA 01890
      2 Highland Ave, Winchester, MA 01890
      /23

      Est $2,357,219 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,014 Sq Ft

      2 Highland Ave, Winchester, MA 01890

      2 Highland Ave, Winchester, MA 01890
    • 6 Dana Ave, Winchester, MA 01890
      6 Dana Ave, Winchester, MA 01890
      6 Dana Ave, Winchester, MA 01890
      /30

      Est $1,518,005 Not Listed For Sale

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

      6 Dana Ave, Winchester, MA 01890

      6 Dana Ave, Winchester, MA 01890
    • 4 Highland Terrace, Winchester, MA 01890
      4 Highland Terrace, Winchester, MA 01890
      4 Highland Terrace, Winchester, MA 01890
      /22

      Est $1,349,798 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,338 Sq Ft

      4 Highland Terrace, Winchester, MA 01890

      4 Highland Terrace, Winchester, MA 01890
    • 3 Valley Rd, Winchester, MA 01890
      3 Valley Rd, Winchester, MA 01890
      3 Valley Rd, Winchester, MA 01890
      /26

      Est $1,429,741 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,016 Sq Ft

      3 Valley Rd, Winchester, MA 01890

      3 Valley Rd, Winchester, MA 01890
    • 7 Valley Rd, Winchester, MA 01890
      7 Valley Rd, Winchester, MA 01890
      7 Valley Rd, Winchester, MA 01890
      /23

      Est $1,483,098 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,599 Sq Ft

      7 Valley Rd, Winchester, MA 01890

      7 Valley Rd, Winchester, MA 01890
    • 11 Valley Rd, Winchester, MA 01890
      11 Valley Rd, Winchester, MA 01890
      11 Valley Rd, Winchester, MA 01890
      /26

      Est $1,540,243 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,327 Sq Ft

      11 Valley Rd, Winchester, MA 01890

      11 Valley Rd, Winchester, MA 01890
    • 149 Forest St, Winchester, MA 01890
      149 Forest St, Winchester, MA 01890
      149 Forest St, Winchester, MA 01890
      /23

      Est $1,245,364 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,480 Sq Ft

      149 Forest St, Winchester, MA 01890

      149 Forest St, Winchester, MA 01890
    • 125 Forest St, Winchester, MA 01890
      125 Forest St, Winchester, MA 01890
      125 Forest St, Winchester, MA 01890
      /11

      Est $1,947,877 Not Listed For Sale

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

      125 Forest St, Winchester, MA 01890

      125 Forest St, Winchester, MA 01890
    • 4 Orient St, Winchester, MA 01890
      4 Orient St, Winchester, MA 01890
      4 Orient St, Winchester, MA 01890
      /29

      Est $1,360,924 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,146 Sq Ft

      4 Orient St, Winchester, MA 01890

      4 Orient St, Winchester, MA 01890
    • 3 Orient St, Winchester, MA 01890
      3 Orient St, Winchester, MA 01890
      3 Orient St, Winchester, MA 01890
      /24

      Est $1,249,283 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,708 Sq Ft

      3 Orient St, Winchester, MA 01890

      3 Orient St, Winchester, MA 01890
    • 525 Washington St Unit 527, Winchester, MA 01890
      525 Washington St Unit 527, Winchester, MA 01890
      525 Washington St Unit 527, Winchester, MA 01890
      /28

      Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,263 Sq Ft

      525 Washington St Unit 527, Winchester, MA 01890

      525 Washington St Unit 527, Winchester, MA 01890
    • 21 Fairmount St, Winchester, MA 01890
      21 Fairmount St, Winchester, MA 01890
      21 Fairmount St, Winchester, MA 01890
      /29

      Est $1,632,597 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,188 Sq Ft

      21 Fairmount St, Winchester, MA 01890

      21 Fairmount St, Winchester, MA 01890
    • 25 Fairmount St, Winchester, MA 01890
      25 Fairmount St, Winchester, MA 01890
      25 Fairmount St, Winchester, MA 01890
      /24

      Est $1,633,560 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,188 Sq Ft

      25 Fairmount St, Winchester, MA 01890

      25 Fairmount St, Winchester, MA 01890
    • 27 Fairmount St, Winchester, MA 01890
      27 Fairmount St, Winchester, MA 01890
      /2

      Est $1,367,939 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,672 Sq Ft

      27 Fairmount St, Winchester, MA 01890

      27 Fairmount St, Winchester, MA 01890
    • 26 Kenwin Rd, Winchester, MA 01890
      26 Kenwin Rd, Winchester, MA 01890
      26 Kenwin Rd, Winchester, MA 01890
      /18

      Est $1,357,692 Not Listed For Sale

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

      26 Kenwin Rd, Winchester, MA 01890

      26 Kenwin Rd, Winchester, MA 01890
    • 18 Kenwin Rd, Winchester, MA 01890
      18 Kenwin Rd, Winchester, MA 01890
      18 Kenwin Rd, Winchester, MA 01890
      /30

      Est $1,474,531 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,105 Sq Ft

      18 Kenwin Rd, Winchester, MA 01890

      18 Kenwin Rd, Winchester, MA 01890
    • 23 Kenwin Rd, Winchester, MA 01890
      23 Kenwin Rd, Winchester, MA 01890
      23 Kenwin Rd, Winchester, MA 01890
      /20

      Est $1,594,981 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,166 Sq Ft

      23 Kenwin Rd, Winchester, MA 01890

      23 Kenwin Rd, Winchester, MA 01890
    • 27 Kenwin Rd, Winchester, MA 01890
      27 Kenwin Rd, Winchester, MA 01890
      27 Kenwin Rd, Winchester, MA 01890
      /12

      Est $1,391,993 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,399 Sq Ft

      27 Kenwin Rd, Winchester, MA 01890

      27 Kenwin Rd, Winchester, MA 01890
    • 35 Kenwin Rd, Winchester, MA 01890
      35 Kenwin Rd, Winchester, MA 01890
      35 Kenwin Rd, Winchester, MA 01890
      /12

      Est $1,340,520 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,922 Sq Ft

      35 Kenwin Rd, Winchester, MA 01890

      35 Kenwin Rd, Winchester, MA 01890
    • 37 Kenwin Rd, Winchester, MA 01890
      37 Kenwin Rd, Winchester, MA 01890
      37 Kenwin Rd, Winchester, MA 01890
      /31

      Est $1,364,726 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,779 Sq Ft

      37 Kenwin Rd, Winchester, MA 01890

      37 Kenwin Rd, Winchester, MA 01890
    • 34 Grayson Rd, Winchester, MA 01890
      34 Grayson Rd, Winchester, MA 01890
      34 Grayson Rd, Winchester, MA 01890
      /24

      Est $1,345,502 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,550 Sq Ft

      34 Grayson Rd, Winchester, MA 01890

      34 Grayson Rd, Winchester, MA 01890
    • 18 Grayson Rd, Winchester, MA 01890
      18 Grayson Rd, Winchester, MA 01890
      18 Grayson Rd, Winchester, MA 01890
      /19

      Est $1,511,714 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,204 Sq Ft

      18 Grayson Rd, Winchester, MA 01890

      18 Grayson Rd, Winchester, MA 01890
    • 10 Bonad Rd, Winchester, MA 01890
      10 Bonad Rd, Winchester, MA 01890
      10 Bonad Rd, Winchester, MA 01890
      /22

      Est $1,223,789 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 1,566 Sq Ft

      10 Bonad Rd, Winchester, MA 01890

      10 Bonad Rd, Winchester, MA 01890
    • 38 Englewood Rd, Winchester, MA 01890
      38 Englewood Rd, Winchester, MA 01890
      38 Englewood Rd, Winchester, MA 01890
      /33

      Est $1,314,817 Not Listed For Sale

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

      38 Englewood Rd, Winchester, MA 01890

      38 Englewood Rd, Winchester, MA 01890
    • 85 Highland Ave, Winchester, MA 01890
      85 Highland Ave, Winchester, MA 01890
      85 Highland Ave, Winchester, MA 01890
      /41

      Est $1,594,988 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,158 Sq Ft

      85 Highland Ave, Winchester, MA 01890

      85 Highland Ave, Winchester, MA 01890
    • 15 Bonad Rd, Winchester, MA 01890
      15 Bonad Rd, Winchester, MA 01890
      15 Bonad Rd, Winchester, MA 01890
      /33

      Est $1,492,761 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,837 Sq Ft

      15 Bonad Rd, Winchester, MA 01890

      15 Bonad Rd, Winchester, MA 01890
    • 1 Andrea Cir, Winchester, MA 01890
      1 Andrea Cir, Winchester, MA 01890
      1 Andrea Cir, Winchester, MA 01890
      /28

      Est $1,999,267 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,822 Sq Ft

      1 Andrea Cir, Winchester, MA 01890

      1 Andrea Cir, Winchester, MA 01890
    • 2 Magnolia Way, Winchester, MA 01890
      2 Magnolia Way, Winchester, MA 01890
      2 Magnolia Way, Winchester, MA 01890
      /30

      Est $2,506,708 Not Listed For Sale

      • 4 Beds
      • 5 Baths
      • 6,220 Sq Ft

      2 Magnolia Way, Winchester, MA 01890

      2 Magnolia Way, Winchester, MA 01890

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