1,483

Winchester Highlands Homes

Section Image
    • 21 Prince Ave, Winchester, MA 01890
      21 Prince Ave, Winchester, MA 01890
      21 Prince Ave, Winchester, MA 01890
      /41

      Est $1,412,870 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,301 Sq Ft

      21 Prince Ave, Winchester, MA 01890

      21 Prince Ave, Winchester, MA 01890
    • 27 Governors Ave, Winchester, MA 01890
      27 Governors Ave, Winchester, MA 01890
      27 Governors Ave, Winchester, MA 01890
      /33

      Est $1,327,030 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,093 Sq Ft

      27 Governors Ave, Winchester, MA 01890

      27 Governors Ave, Winchester, MA 01890
    • 64 Highland Ave Unit 11, Winchester, MA 01890
      64 Highland Ave Unit 11, Winchester, MA 01890
      64 Highland Ave Unit 11, Winchester, MA 01890
      /23

      Est $935,919 Not Listed For Sale

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

      64 Highland Ave Unit 11, Winchester, MA 01890

      64 Highland Ave Unit 11, Winchester, MA 01890
    • 64 Highland Ave Unit 5, Winchester, MA 01890
      64 Highland Ave Unit 5, Winchester, MA 01890
      64 Highland Ave Unit 5, Winchester, MA 01890
      /42

      Est $484,577 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 734 Sq Ft

      64 Highland Ave Unit 5, Winchester, MA 01890

      64 Highland Ave Unit 5, Winchester, MA 01890
    • 24 Hillcrest Pkwy, Winchester, MA 01890
      24 Hillcrest Pkwy, Winchester, MA 01890
      24 Hillcrest Pkwy, Winchester, MA 01890
      /38

      Est $1,562,229 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,147 Sq Ft

      24 Hillcrest Pkwy, Winchester, MA 01890

      24 Hillcrest Pkwy, Winchester, MA 01890
    • 5 Ainsworth Rd, Winchester, MA 01890
      5 Ainsworth Rd, Winchester, MA 01890
      5 Ainsworth Rd, Winchester, MA 01890
      /28

      Est $2,036,455 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,288 Sq Ft

      5 Ainsworth Rd, Winchester, MA 01890

      5 Ainsworth Rd, Winchester, MA 01890
    • 11 Dana Ave, Winchester, MA 01890
      11 Dana Ave, Winchester, MA 01890
      11 Dana Ave, Winchester, MA 01890
      /42

      Est $1,672,130 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,624 Sq Ft

      11 Dana Ave, Winchester, MA 01890

      11 Dana Ave, Winchester, MA 01890
    • 7 Chisholm Rd, Winchester, MA 01890
      7 Chisholm Rd, Winchester, MA 01890
      7 Chisholm Rd, Winchester, MA 01890
      /31

      Est $969,243 Not Listed For Sale

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

      7 Chisholm Rd, Winchester, MA 01890

      7 Chisholm Rd, Winchester, MA 01890
    • 9 Valley Rd, Winchester, MA 01890
      9 Valley Rd, Winchester, MA 01890
      9 Valley Rd, Winchester, MA 01890
      /30

      Est $1,290,440 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,941 Sq Ft

      9 Valley Rd, Winchester, MA 01890

      9 Valley Rd, Winchester, MA 01890
    • 1 Orient St, Winchester, MA 01890
      1 Orient St, Winchester, MA 01890
      1 Orient St, Winchester, MA 01890
      /42

      Est $1,434,620 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,664 Sq Ft

      1 Orient St, Winchester, MA 01890

      1 Orient St, Winchester, MA 01890
    • 29 Kenwin Rd, Winchester, MA 01890
      29 Kenwin Rd, Winchester, MA 01890
      29 Kenwin Rd, Winchester, MA 01890
      /35

      Est $1,450,536 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,132 Sq Ft

      29 Kenwin Rd, Winchester, MA 01890

      29 Kenwin Rd, Winchester, MA 01890
    • 32 Grayson Rd, Winchester, MA 01890
      32 Grayson Rd, Winchester, MA 01890
      32 Grayson Rd, Winchester, MA 01890
      /42

      Est $1,467,039 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,996 Sq Ft

      32 Grayson Rd, Winchester, MA 01890

      32 Grayson Rd, Winchester, MA 01890
    • 4 Bonad Rd, Winchester, MA 01890
      4 Bonad Rd, Winchester, MA 01890
      4 Bonad Rd, Winchester, MA 01890
      /39

      Est $1,361,541 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,240 Sq Ft

      4 Bonad Rd, Winchester, MA 01890

      4 Bonad Rd, Winchester, MA 01890
    • 14 Bonad Rd, Winchester, MA 01890
      14 Bonad Rd, Winchester, MA 01890
      14 Bonad Rd, Winchester, MA 01890
      /42

      Est $1,732,611 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,516 Sq Ft

      14 Bonad Rd, Winchester, MA 01890

      14 Bonad Rd, Winchester, MA 01890
    • 12 Keenan Dr, Winchester, MA 01890
      12 Keenan Dr, Winchester, MA 01890
      12 Keenan Dr, Winchester, MA 01890
      /37

      Est $2,154,584 Not Listed For Sale

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

      12 Keenan Dr, Winchester, MA 01890

      12 Keenan Dr, Winchester, MA 01890
    • 10 Ware Rd, Winchester, MA 01890
      10 Ware Rd, Winchester, MA 01890
      10 Ware Rd, Winchester, MA 01890
      /42

      Est $1,498,480 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,265 Sq Ft

      10 Ware Rd, Winchester, MA 01890

      10 Ware Rd, Winchester, MA 01890
    • 4 Ware Rd, Winchester, MA 01890
      4 Ware Rd, Winchester, MA 01890
      4 Ware Rd, Winchester, MA 01890
      /21

      Est $1,112,921 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,085 Sq Ft

      4 Ware Rd, Winchester, MA 01890

      4 Ware Rd, Winchester, MA 01890
    • 11 Polk Rd, Winchester, MA 01890
      11 Polk Rd, Winchester, MA 01890
      11 Polk Rd, Winchester, MA 01890
      /29

      Est $2,067,272 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,525 Sq Ft

      11 Polk Rd, Winchester, MA 01890

      11 Polk Rd, Winchester, MA 01890
    • 17 Bellevue Ave, Winchester, MA 01890
      17 Bellevue Ave, Winchester, MA 01890
      17 Bellevue Ave, Winchester, MA 01890
      /33

      Est $1,158,078 Not Listed For Sale

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

      17 Bellevue Ave, Winchester, MA 01890

      17 Bellevue Ave, Winchester, MA 01890
    • 16 Bellevue Ave, Winchester, MA 01890
      16 Bellevue Ave, Winchester, MA 01890
      16 Bellevue Ave, Winchester, MA 01890
      /31

      Est $1,138,055 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,791 Sq Ft

      16 Bellevue Ave, Winchester, MA 01890

      16 Bellevue Ave, Winchester, MA 01890
    • 19 Churchill Rd, Winchester, MA 01890
      19 Churchill Rd, Winchester, MA 01890
      19 Churchill Rd, Winchester, MA 01890
      /37

      Est $1,197,273 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,295 Sq Ft

      19 Churchill Rd, Winchester, MA 01890

      19 Churchill Rd, Winchester, MA 01890
    • 7 Grant Rd, Winchester, MA 01890
      7 Grant Rd, Winchester, MA 01890
      7 Grant Rd, Winchester, MA 01890
      /39

      Est $1,147,176 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,034 Sq Ft

      7 Grant Rd, Winchester, MA 01890

      7 Grant Rd, Winchester, MA 01890
    • 41 Sunset Rd, Winchester, MA 01890
      41 Sunset Rd, Winchester, MA 01890
      41 Sunset Rd, Winchester, MA 01890
      /39

      Est $1,400,472 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,544 Sq Ft

      41 Sunset Rd, Winchester, MA 01890

      41 Sunset Rd, Winchester, MA 01890
    • 156 Forest St, Winchester, MA 01890
      156 Forest St, Winchester, MA 01890
      156 Forest St, Winchester, MA 01890
      /38

      Est $1,405,149 Not Listed For Sale

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

      156 Forest St, Winchester, MA 01890

      156 Forest St, Winchester, MA 01890
    • 18 Royalston Ave, Winchester, MA 01890
      18 Royalston Ave, Winchester, MA 01890
      18 Royalston Ave, Winchester, MA 01890
      /42

      Est $2,689,945 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 5,535 Sq Ft

      18 Royalston Ave, Winchester, MA 01890

      18 Royalston Ave, Winchester, MA 01890
    • 23 Sunset Rd, Winchester, MA 01890
      23 Sunset Rd, Winchester, MA 01890
      23 Sunset Rd, Winchester, MA 01890
      /25

      Est $2,261,682 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 3,988 Sq Ft

      23 Sunset Rd, Winchester, MA 01890

      23 Sunset Rd, Winchester, MA 01890
    • 124 Forest St, Winchester, MA 01890
      124 Forest St, Winchester, MA 01890
      124 Forest St, Winchester, MA 01890
      /42

      Est $1,508,324 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,534 Sq Ft

      124 Forest St, Winchester, MA 01890

      124 Forest St, Winchester, MA 01890
    • 120 Forest St, Winchester, MA 01890
      120 Forest St, Winchester, MA 01890
      120 Forest St, Winchester, MA 01890
      /40

      Est $1,629,608 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,613 Sq Ft

      120 Forest St, Winchester, MA 01890

      120 Forest St, Winchester, MA 01890
    • 116 Forest St, Winchester, MA 01890
      116 Forest St, Winchester, MA 01890
      116 Forest St, Winchester, MA 01890
      /38

      Est $1,052,854 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,106 Sq Ft

      116 Forest St, Winchester, MA 01890

      116 Forest St, Winchester, MA 01890
    • 501 Washington St Unit A, Winchester, MA 01890
      501 Washington St Unit A, Winchester, MA 01890
      501 Washington St Unit A, Winchester, MA 01890
      /31

      Est $826,640 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,360 Sq Ft

      501 Washington St Unit A, Winchester, MA 01890

      501 Washington St Unit A, Winchester, MA 01890
    • 4 Abby Rd, Winchester, MA 01890
      4 Abby Rd, Winchester, MA 01890
      4 Abby Rd, Winchester, MA 01890
      /38

      Est $2,934,094 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 5,471 Sq Ft

      4 Abby Rd, Winchester, MA 01890

      4 Abby Rd, Winchester, MA 01890
    • 11 Irving St, Winchester, MA 01890
      11 Irving St, Winchester, MA 01890
      11 Irving St, Winchester, MA 01890
      /10

      Not Listed For Sale

      • 8 Beds
      • 6 Baths
      • 4,535 Sq Ft

      11 Irving St, Winchester, MA 01890

      11 Irving St, Winchester, MA 01890
    • 6 Cross St, Winchester, MA 01890
      6 Cross St, Winchester, MA 01890
      6 Cross St, Winchester, MA 01890
      /41

      Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 2,652 Sq Ft

      6 Cross St, Winchester, MA 01890

      6 Cross St, Winchester, MA 01890
    • 2 Reservoir St, Winchester, MA 01890
      2 Reservoir St, Winchester, MA 01890
      2 Reservoir St, Winchester, MA 01890
      /39

      Est $2,316,968 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 4,267 Sq Ft

      2 Reservoir St, Winchester, MA 01890

      2 Reservoir St, Winchester, MA 01890
    • 67 Florence St Unit 67, Winchester, MA 01890
      67 Florence St Unit 67, Winchester, MA 01890
      67 Florence St Unit 67, Winchester, MA 01890
      /17

      Est $728,601 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,077 Sq Ft

      67 Florence St Unit 67, Winchester, MA 01890

      67 Florence St Unit 67, Winchester, MA 01890
    • 23 Garfield Ave, Winchester, MA 01890
      23 Garfield Ave, Winchester, MA 01890
      23 Garfield Ave, Winchester, MA 01890
      /38

      Est $1,209,546 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,012 Sq Ft

      23 Garfield Ave, Winchester, MA 01890

      23 Garfield Ave, Winchester, MA 01890
    • 9 Governors Ave Unit 2, Winchester, MA 01890
      9 Governors Ave Unit 2, Winchester, MA 01890
      9 Governors Ave Unit 2, Winchester, MA 01890
      /30

      Est $817,389 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,667 Sq Ft

      9 Governors Ave Unit 2, Winchester, MA 01890

      9 Governors Ave Unit 2, Winchester, MA 01890
    • 8 Cardinal St, Winchester, MA 01890
      8 Cardinal St, Winchester, MA 01890
      8 Cardinal St, Winchester, MA 01890
      /25

      Est $1,704,673 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,668 Sq Ft

      8 Cardinal St, Winchester, MA 01890

      8 Cardinal St, Winchester, MA 01890
    • 44 Brookside Ave, Winchester, MA 01890
      44 Brookside Ave, Winchester, MA 01890
      44 Brookside Ave, Winchester, MA 01890
      /42

      Est $1,822,711 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,845 Sq Ft

      44 Brookside Ave, Winchester, MA 01890

      44 Brookside Ave, Winchester, MA 01890
    • 27 Garfield Ave, Winchester, MA 01890
      27 Garfield Ave, Winchester, MA 01890
      27 Garfield Ave, Winchester, MA 01890
      /36

      Est $974,119 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,288 Sq Ft

      27 Garfield Ave, Winchester, MA 01890

      27 Garfield Ave, Winchester, MA 01890

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