Recently Viewed Properties
47 Results

Winchester Highlands Real Estate & Homes For Sale

Add

Oops! We need you to add a location.
more
Selecting these elements will cause content on the page to be updated. Near by
NEARBY
    Selecting these elements will cause content on the page to be updated. History
    HISTORY
      Save this Search
      Filters
      Selection will refresh the page with new results. properties
      —
      You’ll get email updates when new properties matching this criteria go on the market. You can also run these searches quickly under “Properties & Searches” at the top of every page.
      Selection will refresh the page with new results.
      Selection will refresh the page with new results. properties
      Property Type
      PRICE
      to
      BEDROOMS
      BATHROOMS
      STATUS (only include)
      Lot Sizeto
      FEATURES

      Add

      Max keywords reached
      Save this Search
      Hide Map
      Order By

      Due to MLS rules, you are able to view 47 of 87 matching properties without signing in. To view all properties please . Not Registered? Sign Up

      Save this Search

      47 Results
      Order By

      Use previous and next buttons to navigate

      247 Washington St, Winchester, MA 01890 - Photo 1 247 Washington St, Winchester, MA 01890 - Photo 2 247 Washington St, Winchester, MA 01890 - Photo 3 247 Washington St, Winchester, MA 01890 - Photo 4 247 Washington St, Winchester, MA 01890 - Photo 5 247 Washington St, Winchester, MA 01890 - Photo 6 247 Washington St, Winchester, MA 01890 - Photo 7 247 Washington St, Winchester, MA 01890 - Photo 8 247 Washington St, Winchester, MA 01890 - Photo 9 247 Washington St, Winchester, MA 01890 - Photo 10 247 Washington St, Winchester, MA 01890 - Photo 11 247 Washington St, Winchester, MA 01890 - Photo 12 247 Washington St, Winchester, MA 01890 - Photo 13 247 Washington St, Winchester, MA 01890 - Photo 14 247 Washington St, Winchester, MA 01890 - Photo 15 247 Washington St, Winchester, MA 01890 - Photo 16 247 Washington St, Winchester, MA 01890 - Photo 17 247 Washington St, Winchester, MA 01890 - Photo 18 247 Washington St, Winchester, MA 01890 - Photo 19 247 Washington St, Winchester, MA 01890 - Photo 20 247 Washington St, Winchester, MA 01890 - Photo 21 247 Washington St, Winchester, MA 01890 - Photo 22 247 Washington St, Winchester, MA 01890 - Photo 23
      Just Listed

      1/23

      Open House
      Fri7/175-6

      247 Washington St  #11  Winchester, MA 01890

      $729,000
      • Townhouse
      • Active
      • MLS # 73549877
      • Updated 1 day ago
      • 3
        Beds
      • 2
        Full Baths
      • 1
        Partial Bath
      • 3
        Total Baths
      • 1,494
        Sq. Ft.
      Listed by Jessie Joo (617) 831-6999

      Use previous and next buttons to navigate

      47 Water St, Winchester, MA 01890 - Photo 1 47 Water St, Winchester, MA 01890 - Photo 2 47 Water St, Winchester, MA 01890 - Photo 3 47 Water St, Winchester, MA 01890 - Photo 4 47 Water St, Winchester, MA 01890 - Photo 5 47 Water St, Winchester, MA 01890 - Photo 6 47 Water St, Winchester, MA 01890 - Photo 7 47 Water St, Winchester, MA 01890 - Photo 8 47 Water St, Winchester, MA 01890 - Photo 9 47 Water St, Winchester, MA 01890 - Photo 10 47 Water St, Winchester, MA 01890 - Photo 11 47 Water St, Winchester, MA 01890 - Photo 12 47 Water St, Winchester, MA 01890 - Photo 13 47 Water St, Winchester, MA 01890 - Photo 14 47 Water St, Winchester, MA 01890 - Photo 15 47 Water St, Winchester, MA 01890 - Photo 16 47 Water St, Winchester, MA 01890 - Photo 17 47 Water St, Winchester, MA 01890 - Photo 18 47 Water St, Winchester, MA 01890 - Photo 19 47 Water St, Winchester, MA 01890 - Photo 20 47 Water St, Winchester, MA 01890 - Photo 21 47 Water St, Winchester, MA 01890 - Photo 22 47 Water St, Winchester, MA 01890 - Photo 23 47 Water St, Winchester, MA 01890 - Photo 24 47 Water St, Winchester, MA 01890 - Photo 25 47 Water St, Winchester, MA 01890 - Photo 26 47 Water St, Winchester, MA 01890 - Photo 27 47 Water St, Winchester, MA 01890 - Photo 28 47 Water St, Winchester, MA 01890 - Photo 29 47 Water St, Winchester, MA 01890 - Photo 30
      Just Listed

      1/30

      Open House
      Sat7/1811-1

      47 Water St  Winchester, MA 01890

      $950,000
      • Single Family
      • Active
      • MLS # 73549935
      • Updated 1 day ago
      • 3
        Beds
      • 1
        Full Bath
      • 1
        Total Bath
      • 1,356
        Sq. Ft.
      • 2
        Car Garage

      Use previous and next buttons to navigate

      52 Salem St, Winchester, MA 01890 - Photo 1 52 Salem St, Winchester, MA 01890 - Photo 2 52 Salem St, Winchester, MA 01890 - Photo 3 52 Salem St, Winchester, MA 01890 - Photo 4 52 Salem St, Winchester, MA 01890 - Photo 5 52 Salem St, Winchester, MA 01890 - Photo 6 52 Salem St, Winchester, MA 01890 - Photo 7 52 Salem St, Winchester, MA 01890 - Photo 8 52 Salem St, Winchester, MA 01890 - Photo 9 52 Salem St, Winchester, MA 01890 - Photo 10 52 Salem St, Winchester, MA 01890 - Photo 11 52 Salem St, Winchester, MA 01890 - Photo 12 52 Salem St, Winchester, MA 01890 - Photo 13 52 Salem St, Winchester, MA 01890 - Photo 14 52 Salem St, Winchester, MA 01890 - Photo 15 52 Salem St, Winchester, MA 01890 - Photo 16 52 Salem St, Winchester, MA 01890 - Photo 17 52 Salem St, Winchester, MA 01890 - Photo 18 52 Salem St, Winchester, MA 01890 - Photo 19 52 Salem St, Winchester, MA 01890 - Photo 20 52 Salem St, Winchester, MA 01890 - Photo 21 52 Salem St, Winchester, MA 01890 - Photo 22 52 Salem St, Winchester, MA 01890 - Photo 23 52 Salem St, Winchester, MA 01890 - Photo 24 52 Salem St, Winchester, MA 01890 - Photo 25 52 Salem St, Winchester, MA 01890 - Photo 26 52 Salem St, Winchester, MA 01890 - Photo 27 52 Salem St, Winchester, MA 01890 - Photo 28
      Just Listed

      1/28

      Open House
      Sat7/1812-1:30

      52 Salem St  #52  Winchester, MA 01890

      $1,150,000
      • Single Family
      • Active
      • MLS # 73549499
      • Updated 2 days ago
      • 3
        Beds
      • 2
        Full Baths
      • 1
        Partial Bath
      • 3
        Total Baths
      • 2,004
        Sq. Ft.

      Use previous and next buttons to navigate

      52 Salem St, Winchester, MA 01890 - Photo 1 52 Salem St, Winchester, MA 01890 - Photo 2 52 Salem St, Winchester, MA 01890 - Photo 3 52 Salem St, Winchester, MA 01890 - Photo 4 52 Salem St, Winchester, MA 01890 - Photo 5 52 Salem St, Winchester, MA 01890 - Photo 6 52 Salem St, Winchester, MA 01890 - Photo 7 52 Salem St, Winchester, MA 01890 - Photo 8 52 Salem St, Winchester, MA 01890 - Photo 9 52 Salem St, Winchester, MA 01890 - Photo 10 52 Salem St, Winchester, MA 01890 - Photo 11 52 Salem St, Winchester, MA 01890 - Photo 12 52 Salem St, Winchester, MA 01890 - Photo 13 52 Salem St, Winchester, MA 01890 - Photo 14 52 Salem St, Winchester, MA 01890 - Photo 15 52 Salem St, Winchester, MA 01890 - Photo 16 52 Salem St, Winchester, MA 01890 - Photo 17 52 Salem St, Winchester, MA 01890 - Photo 18 52 Salem St, Winchester, MA 01890 - Photo 19 52 Salem St, Winchester, MA 01890 - Photo 20 52 Salem St, Winchester, MA 01890 - Photo 21 52 Salem St, Winchester, MA 01890 - Photo 22 52 Salem St, Winchester, MA 01890 - Photo 23 52 Salem St, Winchester, MA 01890 - Photo 24 52 Salem St, Winchester, MA 01890 - Photo 25 52 Salem St, Winchester, MA 01890 - Photo 26 52 Salem St, Winchester, MA 01890 - Photo 27 52 Salem St, Winchester, MA 01890 - Photo 28
      Just Listed

      1/28

      Open House
      Sat7/1812-1:30

      52 Salem St  #52  Winchester, MA 01890

      $1,150,000
      • Townhouse
      • Active
      • MLS # 73549484
      • Updated 2 days ago
      • 3
        Beds
      • 2
        Full Baths
      • 1
        Partial Bath
      • 3
        Total Baths
      • 2,004
        Sq. Ft.

      Use previous and next buttons to navigate

      2 Olde Lyme Rd, Winchester, MA 01890 - Photo 1 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 2 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 3 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 4 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 5 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 6 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 7 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 8 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 9 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 10 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 11 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 12 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 13 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 14 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 15 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 16 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 17 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 18 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 19 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 20 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 21 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 22 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 23 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 24 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 25 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 26 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 27 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 28 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 29 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 30 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 31 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 32 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 33 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 34 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 35 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 36 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 37 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 38 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 39 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 40 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 41 2 Olde Lyme Rd, Winchester, MA 01890 - Photo 42
      Just Listed

      1/42

      Open House
      Sat7/1811-12:30

      2 Olde Lyme Rd  Winchester, MA 01890

      $1,699,000
      • Single Family
      • Active
      • MLS # 73549106
      • Updated 2 days ago
      • 3
        Beds
      • 3
        Full Baths
      • 1
        Partial Bath
      • 4
        Total Baths
      • 2,513
        Sq. Ft.
      • 2
        Car Garage

      Use previous and next buttons to navigate

      200 Swanton, Winchester, MA 01890 - Photo 1 200 Swanton, Winchester, MA 01890 - Photo 2 200 Swanton, Winchester, MA 01890 - Photo 3 200 Swanton, Winchester, MA 01890 - Photo 4 200 Swanton, Winchester, MA 01890 - Photo 5 200 Swanton, Winchester, MA 01890 - Photo 6 200 Swanton, Winchester, MA 01890 - Photo 7 200 Swanton, Winchester, MA 01890 - Photo 8 200 Swanton, Winchester, MA 01890 - Photo 9 200 Swanton, Winchester, MA 01890 - Photo 10 200 Swanton, Winchester, MA 01890 - Photo 11 200 Swanton, Winchester, MA 01890 - Photo 12 200 Swanton, Winchester, MA 01890 - Photo 13 200 Swanton, Winchester, MA 01890 - Photo 14 200 Swanton, Winchester, MA 01890 - Photo 15 200 Swanton, Winchester, MA 01890 - Photo 16 200 Swanton, Winchester, MA 01890 - Photo 17 200 Swanton, Winchester, MA 01890 - Photo 18 200 Swanton, Winchester, MA 01890 - Photo 19 200 Swanton, Winchester, MA 01890 - Photo 20 200 Swanton, Winchester, MA 01890 - Photo 21 200 Swanton, Winchester, MA 01890 - Photo 22 200 Swanton, Winchester, MA 01890 - Photo 23 200 Swanton, Winchester, MA 01890 - Photo 24 200 Swanton, Winchester, MA 01890 - Photo 25 200 Swanton, Winchester, MA 01890 - Photo 26 200 Swanton, Winchester, MA 01890 - Photo 27 200 Swanton, Winchester, MA 01890 - Photo 28
      Just Listed

      1/28

      200 Swanton  #L8  Winchester, MA 01890

      $288,750
      • Condo
      • Active
      • MLS # 73548413
      • Updated 1 day ago
      • 1
        Full Bath
      • 1
        Total Bath
      • 388
        Sq. Ft.

      Use previous and next buttons to navigate

      10 Dartmouth St, Winchester, MA 01890 - Photo 1 10 Dartmouth St, Winchester, MA 01890 - Photo 2 10 Dartmouth St, Winchester, MA 01890 - Photo 3 10 Dartmouth St, Winchester, MA 01890 - Photo 4 10 Dartmouth St, Winchester, MA 01890 - Photo 5 10 Dartmouth St, Winchester, MA 01890 - Photo 6 10 Dartmouth St, Winchester, MA 01890 - Photo 7 10 Dartmouth St, Winchester, MA 01890 - Photo 8 10 Dartmouth St, Winchester, MA 01890 - Photo 9 10 Dartmouth St, Winchester, MA 01890 - Photo 10 10 Dartmouth St, Winchester, MA 01890 - Photo 11 10 Dartmouth St, Winchester, MA 01890 - Photo 12 10 Dartmouth St, Winchester, MA 01890 - Photo 13 10 Dartmouth St, Winchester, MA 01890 - Photo 14 10 Dartmouth St, Winchester, MA 01890 - Photo 15 10 Dartmouth St, Winchester, MA 01890 - Photo 16 10 Dartmouth St, Winchester, MA 01890 - Photo 17 10 Dartmouth St, Winchester, MA 01890 - Photo 18 10 Dartmouth St, Winchester, MA 01890 - Photo 19 10 Dartmouth St, Winchester, MA 01890 - Photo 20 10 Dartmouth St, Winchester, MA 01890 - Photo 21 10 Dartmouth St, Winchester, MA 01890 - Photo 22 10 Dartmouth St, Winchester, MA 01890 - Photo 23 10 Dartmouth St, Winchester, MA 01890 - Photo 24 10 Dartmouth St, Winchester, MA 01890 - Photo 25 10 Dartmouth St, Winchester, MA 01890 - Photo 26 10 Dartmouth St, Winchester, MA 01890 - Photo 27 10 Dartmouth St, Winchester, MA 01890 - Photo 28 10 Dartmouth St, Winchester, MA 01890 - Photo 29 10 Dartmouth St, Winchester, MA 01890 - Photo 30 10 Dartmouth St, Winchester, MA 01890 - Photo 31 10 Dartmouth St, Winchester, MA 01890 - Photo 32 10 Dartmouth St, Winchester, MA 01890 - Photo 33 10 Dartmouth St, Winchester, MA 01890 - Photo 34 10 Dartmouth St, Winchester, MA 01890 - Photo 35 10 Dartmouth St, Winchester, MA 01890 - Photo 36 10 Dartmouth St, Winchester, MA 01890 - Photo 37 10 Dartmouth St, Winchester, MA 01890 - Photo 38 10 Dartmouth St, Winchester, MA 01890 - Photo 39 10 Dartmouth St, Winchester, MA 01890 - Photo 40 10 Dartmouth St, Winchester, MA 01890 - Photo 41 10 Dartmouth St, Winchester, MA 01890 - Photo 42
      Just Listed

      1/42

      Open House
      Sun7/1911-12:30

      10 Dartmouth St  Winchester, MA 01890

      $2,999,000
      • Single Family
      • Active
      • MLS # 73548103
      • Updated 2 days ago
      • 5
        Beds
      • 2
        Full Baths
      • 2
        Partial Baths
      • 4
        Total Baths
      • 4,028
        Sq. Ft.
      • 2
        Car Garage

      Use previous and next buttons to navigate

      46 Clark St, Winchester, MA 01890 - Photo 1 46 Clark St, Winchester, MA 01890 - Photo 2 46 Clark St, Winchester, MA 01890 - Photo 3 46 Clark St, Winchester, MA 01890 - Photo 4 46 Clark St, Winchester, MA 01890 - Photo 5 46 Clark St, Winchester, MA 01890 - Photo 6 46 Clark St, Winchester, MA 01890 - Photo 7 46 Clark St, Winchester, MA 01890 - Photo 8 46 Clark St, Winchester, MA 01890 - Photo 9 46 Clark St, Winchester, MA 01890 - Photo 10 46 Clark St, Winchester, MA 01890 - Photo 11 46 Clark St, Winchester, MA 01890 - Photo 12 46 Clark St, Winchester, MA 01890 - Photo 13 46 Clark St, Winchester, MA 01890 - Photo 14 46 Clark St, Winchester, MA 01890 - Photo 15 46 Clark St, Winchester, MA 01890 - Photo 16 46 Clark St, Winchester, MA 01890 - Photo 17 46 Clark St, Winchester, MA 01890 - Photo 18 46 Clark St, Winchester, MA 01890 - Photo 19 46 Clark St, Winchester, MA 01890 - Photo 20 46 Clark St, Winchester, MA 01890 - Photo 21 46 Clark St, Winchester, MA 01890 - Photo 22 46 Clark St, Winchester, MA 01890 - Photo 23 46 Clark St, Winchester, MA 01890 - Photo 24 46 Clark St, Winchester, MA 01890 - Photo 25 46 Clark St, Winchester, MA 01890 - Photo 26 46 Clark St, Winchester, MA 01890 - Photo 27 46 Clark St, Winchester, MA 01890 - Photo 28 46 Clark St, Winchester, MA 01890 - Photo 29 46 Clark St, Winchester, MA 01890 - Photo 30 46 Clark St, Winchester, MA 01890 - Photo 31 46 Clark St, Winchester, MA 01890 - Photo 32 46 Clark St, Winchester, MA 01890 - Photo 33 46 Clark St, Winchester, MA 01890 - Photo 34 46 Clark St, Winchester, MA 01890 - Photo 35 46 Clark St, Winchester, MA 01890 - Photo 36

      1/36

      Open House
      Sat7/1812:30-1:30

      46 Clark St  Winchester, MA 01890

      $1,099,000
      • Single Family
      • Active
      • MLS # 73547513
      • Updated 1 day ago
      • 4
        Beds
      • 1
        Full Bath
      • 1
        Partial Bath
      • 2
        Total Baths
      • 1,777
        Sq. Ft.

      Use previous and next buttons to navigate

      241 Ridge St, Winchester, MA 01890 - Photo 1 241 Ridge St, Winchester, MA 01890 - Photo 2 241 Ridge St, Winchester, MA 01890 - Photo 3 241 Ridge St, Winchester, MA 01890 - Photo 4 241 Ridge St, Winchester, MA 01890 - Photo 5 241 Ridge St, Winchester, MA 01890 - Photo 6 241 Ridge St, Winchester, MA 01890 - Photo 7 241 Ridge St, Winchester, MA 01890 - Photo 8 241 Ridge St, Winchester, MA 01890 - Photo 9 241 Ridge St, Winchester, MA 01890 - Photo 10 241 Ridge St, Winchester, MA 01890 - Photo 11 241 Ridge St, Winchester, MA 01890 - Photo 12 241 Ridge St, Winchester, MA 01890 - Photo 13 241 Ridge St, Winchester, MA 01890 - Photo 14 241 Ridge St, Winchester, MA 01890 - Photo 15 241 Ridge St, Winchester, MA 01890 - Photo 16 241 Ridge St, Winchester, MA 01890 - Photo 17 241 Ridge St, Winchester, MA 01890 - Photo 18 241 Ridge St, Winchester, MA 01890 - Photo 19 241 Ridge St, Winchester, MA 01890 - Photo 20 241 Ridge St, Winchester, MA 01890 - Photo 21 241 Ridge St, Winchester, MA 01890 - Photo 22 241 Ridge St, Winchester, MA 01890 - Photo 23 241 Ridge St, Winchester, MA 01890 - Photo 24 241 Ridge St, Winchester, MA 01890 - Photo 25 241 Ridge St, Winchester, MA 01890 - Photo 26 241 Ridge St, Winchester, MA 01890 - Photo 27 241 Ridge St, Winchester, MA 01890 - Photo 28 241 Ridge St, Winchester, MA 01890 - Photo 29 241 Ridge St, Winchester, MA 01890 - Photo 30 241 Ridge St, Winchester, MA 01890 - Photo 31 241 Ridge St, Winchester, MA 01890 - Photo 32 241 Ridge St, Winchester, MA 01890 - Photo 33 241 Ridge St, Winchester, MA 01890 - Photo 34 241 Ridge St, Winchester, MA 01890 - Photo 35 241 Ridge St, Winchester, MA 01890 - Photo 36 241 Ridge St, Winchester, MA 01890 - Photo 37 241 Ridge St, Winchester, MA 01890 - Photo 38 241 Ridge St, Winchester, MA 01890 - Photo 39

      1/39

      241 Ridge St  Winchester, MA 01890

      $1,599,000
      • Single Family
      • Active
      • MLS # 73546455
      • Updated 4 days ago
      • 4
        Beds
      • 2
        Full Baths
      • 2
        Partial Baths
      • 4
        Total Baths
      • 2,480
        Sq. Ft.

      Use previous and next buttons to navigate

      79 Grove St, Winchester, MA 01890 - Photo 1 79 Grove St, Winchester, MA 01890 - Photo 2 79 Grove St, Winchester, MA 01890 - Photo 3 79 Grove St, Winchester, MA 01890 - Photo 4 79 Grove St, Winchester, MA 01890 - Photo 5 79 Grove St, Winchester, MA 01890 - Photo 6 79 Grove St, Winchester, MA 01890 - Photo 7 79 Grove St, Winchester, MA 01890 - Photo 8 79 Grove St, Winchester, MA 01890 - Photo 9 79 Grove St, Winchester, MA 01890 - Photo 10 79 Grove St, Winchester, MA 01890 - Photo 11 79 Grove St, Winchester, MA 01890 - Photo 12 79 Grove St, Winchester, MA 01890 - Photo 13 79 Grove St, Winchester, MA 01890 - Photo 14 79 Grove St, Winchester, MA 01890 - Photo 15 79 Grove St, Winchester, MA 01890 - Photo 16 79 Grove St, Winchester, MA 01890 - Photo 17 79 Grove St, Winchester, MA 01890 - Photo 18 79 Grove St, Winchester, MA 01890 - Photo 19 79 Grove St, Winchester, MA 01890 - Photo 20 79 Grove St, Winchester, MA 01890 - Photo 21 79 Grove St, Winchester, MA 01890 - Photo 22 79 Grove St, Winchester, MA 01890 - Photo 23 79 Grove St, Winchester, MA 01890 - Photo 24 79 Grove St, Winchester, MA 01890 - Photo 25 79 Grove St, Winchester, MA 01890 - Photo 26 79 Grove St, Winchester, MA 01890 - Photo 27 79 Grove St, Winchester, MA 01890 - Photo 28 79 Grove St, Winchester, MA 01890 - Photo 29 79 Grove St, Winchester, MA 01890 - Photo 30 79 Grove St, Winchester, MA 01890 - Photo 31 79 Grove St, Winchester, MA 01890 - Photo 32 79 Grove St, Winchester, MA 01890 - Photo 33 79 Grove St, Winchester, MA 01890 - Photo 34 79 Grove St, Winchester, MA 01890 - Photo 35 79 Grove St, Winchester, MA 01890 - Photo 36 79 Grove St, Winchester, MA 01890 - Photo 37 79 Grove St, Winchester, MA 01890 - Photo 38 79 Grove St, Winchester, MA 01890 - Photo 39 79 Grove St, Winchester, MA 01890 - Photo 40 79 Grove St, Winchester, MA 01890 - Photo 41

      1/41

      Open House
      Sat7/1812-1:30

      79 Grove St  Winchester, MA 01890

      $1,899,000
      • Single Family
      • Active
      • MLS # 73545952
      • Updated 5 days ago
      • 5
        Beds
      • 3
        Full Baths
      • 1
        Partial Bath
      • 4
        Total Baths
      • 3,210
        Sq. Ft.
      • 2
        Car Garage

      Use previous and next buttons to navigate

      52 Middlesex St, Winchester, MA 01890 - Photo 1 52 Middlesex St, Winchester, MA 01890 - Photo 2 52 Middlesex St, Winchester, MA 01890 - Photo 3 52 Middlesex St, Winchester, MA 01890 - Photo 4 52 Middlesex St, Winchester, MA 01890 - Photo 5 52 Middlesex St, Winchester, MA 01890 - Photo 6 52 Middlesex St, Winchester, MA 01890 - Photo 7 52 Middlesex St, Winchester, MA 01890 - Photo 8 52 Middlesex St, Winchester, MA 01890 - Photo 9 52 Middlesex St, Winchester, MA 01890 - Photo 10 52 Middlesex St, Winchester, MA 01890 - Photo 11 52 Middlesex St, Winchester, MA 01890 - Photo 12 52 Middlesex St, Winchester, MA 01890 - Photo 13 52 Middlesex St, Winchester, MA 01890 - Photo 14 52 Middlesex St, Winchester, MA 01890 - Photo 15 52 Middlesex St, Winchester, MA 01890 - Photo 16 52 Middlesex St, Winchester, MA 01890 - Photo 17 52 Middlesex St, Winchester, MA 01890 - Photo 18 52 Middlesex St, Winchester, MA 01890 - Photo 19 52 Middlesex St, Winchester, MA 01890 - Photo 20 52 Middlesex St, Winchester, MA 01890 - Photo 21 52 Middlesex St, Winchester, MA 01890 - Photo 22 52 Middlesex St, Winchester, MA 01890 - Photo 23 52 Middlesex St, Winchester, MA 01890 - Photo 24 52 Middlesex St, Winchester, MA 01890 - Photo 25 52 Middlesex St, Winchester, MA 01890 - Photo 26 52 Middlesex St, Winchester, MA 01890 - Photo 27 52 Middlesex St, Winchester, MA 01890 - Photo 28 52 Middlesex St, Winchester, MA 01890 - Photo 29 52 Middlesex St, Winchester, MA 01890 - Photo 30 52 Middlesex St, Winchester, MA 01890 - Photo 31 52 Middlesex St, Winchester, MA 01890 - Photo 32 52 Middlesex St, Winchester, MA 01890 - Photo 33 52 Middlesex St, Winchester, MA 01890 - Photo 34 52 Middlesex St, Winchester, MA 01890 - Photo 35 52 Middlesex St, Winchester, MA 01890 - Photo 36 52 Middlesex St, Winchester, MA 01890 - Photo 37 52 Middlesex St, Winchester, MA 01890 - Photo 38 52 Middlesex St, Winchester, MA 01890 - Photo 39 52 Middlesex St, Winchester, MA 01890 - Photo 40 52 Middlesex St, Winchester, MA 01890 - Photo 41
      Contingent

      1/41

      52 Middlesex St  #52  Winchester, MA 01890

      $1,195,000
      • Townhouse
      • Contingent
      • MLS # 73546076
      • Updated 1 day ago
      • 4
        Beds
      • 2
        Full Baths
      • 1
        Partial Bath
      • 3
        Total Baths
      • 2,303
        Sq. Ft.

      Use previous and next buttons to navigate

      50 Middlesex St, Winchester, MA 01890 - Photo 1 50 Middlesex St, Winchester, MA 01890 - Photo 2 50 Middlesex St, Winchester, MA 01890 - Photo 3 50 Middlesex St, Winchester, MA 01890 - Photo 4 50 Middlesex St, Winchester, MA 01890 - Photo 5 50 Middlesex St, Winchester, MA 01890 - Photo 6 50 Middlesex St, Winchester, MA 01890 - Photo 7 50 Middlesex St, Winchester, MA 01890 - Photo 8 50 Middlesex St, Winchester, MA 01890 - Photo 9 50 Middlesex St, Winchester, MA 01890 - Photo 10 50 Middlesex St, Winchester, MA 01890 - Photo 11 50 Middlesex St, Winchester, MA 01890 - Photo 12 50 Middlesex St, Winchester, MA 01890 - Photo 13 50 Middlesex St, Winchester, MA 01890 - Photo 14 50 Middlesex St, Winchester, MA 01890 - Photo 15 50 Middlesex St, Winchester, MA 01890 - Photo 16 50 Middlesex St, Winchester, MA 01890 - Photo 17 50 Middlesex St, Winchester, MA 01890 - Photo 18 50 Middlesex St, Winchester, MA 01890 - Photo 19 50 Middlesex St, Winchester, MA 01890 - Photo 20 50 Middlesex St, Winchester, MA 01890 - Photo 21

      1/21

      Open House
      Sat7/1811-12:30

      50 Middlesex St  #50  Winchester, MA 01890

      $799,000
      • Townhouse
      • Active
      • MLS # 73546074
      • Updated 5 days ago
      • 2
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,036
        Sq. Ft.

      Use previous and next buttons to navigate

      9 Plymouth Rd, Winchester, MA 01890 - Photo 1 9 Plymouth Rd, Winchester, MA 01890 - Photo 2 9 Plymouth Rd, Winchester, MA 01890 - Photo 3 9 Plymouth Rd, Winchester, MA 01890 - Photo 4 9 Plymouth Rd, Winchester, MA 01890 - Photo 5 9 Plymouth Rd, Winchester, MA 01890 - Photo 6 9 Plymouth Rd, Winchester, MA 01890 - Photo 7 9 Plymouth Rd, Winchester, MA 01890 - Photo 8 9 Plymouth Rd, Winchester, MA 01890 - Photo 9 9 Plymouth Rd, Winchester, MA 01890 - Photo 10 9 Plymouth Rd, Winchester, MA 01890 - Photo 11 9 Plymouth Rd, Winchester, MA 01890 - Photo 12 9 Plymouth Rd, Winchester, MA 01890 - Photo 13 9 Plymouth Rd, Winchester, MA 01890 - Photo 14 9 Plymouth Rd, Winchester, MA 01890 - Photo 15 9 Plymouth Rd, Winchester, MA 01890 - Photo 16 9 Plymouth Rd, Winchester, MA 01890 - Photo 17 9 Plymouth Rd, Winchester, MA 01890 - Photo 18 9 Plymouth Rd, Winchester, MA 01890 - Photo 19 9 Plymouth Rd, Winchester, MA 01890 - Photo 20 9 Plymouth Rd, Winchester, MA 01890 - Photo 21 9 Plymouth Rd, Winchester, MA 01890 - Photo 22 9 Plymouth Rd, Winchester, MA 01890 - Photo 23 9 Plymouth Rd, Winchester, MA 01890 - Photo 24 9 Plymouth Rd, Winchester, MA 01890 - Photo 25 9 Plymouth Rd, Winchester, MA 01890 - Photo 26 9 Plymouth Rd, Winchester, MA 01890 - Photo 27 9 Plymouth Rd, Winchester, MA 01890 - Photo 28 9 Plymouth Rd, Winchester, MA 01890 - Photo 29 9 Plymouth Rd, Winchester, MA 01890 - Photo 30 9 Plymouth Rd, Winchester, MA 01890 - Photo 31 9 Plymouth Rd, Winchester, MA 01890 - Photo 32 9 Plymouth Rd, Winchester, MA 01890 - Photo 33 9 Plymouth Rd, Winchester, MA 01890 - Photo 34 9 Plymouth Rd, Winchester, MA 01890 - Photo 35 9 Plymouth Rd, Winchester, MA 01890 - Photo 36 9 Plymouth Rd, Winchester, MA 01890 - Photo 37

      1/37

      9 Plymouth Rd  Winchester, MA 01890

      $2,500,000
      • Single Family
      • Active
      • MLS # 73544924
      • Updated 6 days ago
      • 5
        Beds
      • 3
        Full Baths
      • 3
        Total Baths
      • 4,071
        Sq. Ft.
      • 2
        Car Garage

      Use previous and next buttons to navigate

      666 Main St, Winchester, MA 01890 - Photo 1 666 Main St, Winchester, MA 01890 - Photo 2 666 Main St, Winchester, MA 01890 - Photo 3 666 Main St, Winchester, MA 01890 - Photo 4 666 Main St, Winchester, MA 01890 - Photo 5 666 Main St, Winchester, MA 01890 - Photo 6 666 Main St, Winchester, MA 01890 - Photo 7 666 Main St, Winchester, MA 01890 - Photo 8 666 Main St, Winchester, MA 01890 - Photo 9 666 Main St, Winchester, MA 01890 - Photo 10 666 Main St, Winchester, MA 01890 - Photo 11 666 Main St, Winchester, MA 01890 - Photo 12 666 Main St, Winchester, MA 01890 - Photo 13 666 Main St, Winchester, MA 01890 - Photo 14 666 Main St, Winchester, MA 01890 - Photo 15 666 Main St, Winchester, MA 01890 - Photo 16 666 Main St, Winchester, MA 01890 - Photo 17 666 Main St, Winchester, MA 01890 - Photo 18 666 Main St, Winchester, MA 01890 - Photo 19 666 Main St, Winchester, MA 01890 - Photo 20 666 Main St, Winchester, MA 01890 - Photo 21 666 Main St, Winchester, MA 01890 - Photo 22 666 Main St, Winchester, MA 01890 - Photo 23 666 Main St, Winchester, MA 01890 - Photo 24 666 Main St, Winchester, MA 01890 - Photo 25 666 Main St, Winchester, MA 01890 - Photo 26 666 Main St, Winchester, MA 01890 - Photo 27 666 Main St, Winchester, MA 01890 - Photo 28 666 Main St, Winchester, MA 01890 - Photo 29 666 Main St, Winchester, MA 01890 - Photo 30 666 Main St, Winchester, MA 01890 - Photo 31 666 Main St, Winchester, MA 01890 - Photo 32 666 Main St, Winchester, MA 01890 - Photo 33 666 Main St, Winchester, MA 01890 - Photo 34 666 Main St, Winchester, MA 01890 - Photo 35 666 Main St, Winchester, MA 01890 - Photo 36 666 Main St, Winchester, MA 01890 - Photo 37

      1/37

      Open House
      Sat7/1811-12

      666 Main St  #315  Winchester, MA 01890

      $649,900
      • Condo
      • Active
      • MLS # 73543744
      • Updated 11 days ago
      • 2
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,025
        Sq. Ft.

      Use previous and next buttons to navigate

      84 Oak St, Winchester, MA 01890 - Photo 1 84 Oak St, Winchester, MA 01890 - Photo 2 84 Oak St, Winchester, MA 01890 - Photo 3 84 Oak St, Winchester, MA 01890 - Photo 4 84 Oak St, Winchester, MA 01890 - Photo 5 84 Oak St, Winchester, MA 01890 - Photo 6 84 Oak St, Winchester, MA 01890 - Photo 7 84 Oak St, Winchester, MA 01890 - Photo 8 84 Oak St, Winchester, MA 01890 - Photo 9 84 Oak St, Winchester, MA 01890 - Photo 10 84 Oak St, Winchester, MA 01890 - Photo 11 84 Oak St, Winchester, MA 01890 - Photo 12 84 Oak St, Winchester, MA 01890 - Photo 13 84 Oak St, Winchester, MA 01890 - Photo 14 84 Oak St, Winchester, MA 01890 - Photo 15 84 Oak St, Winchester, MA 01890 - Photo 16 84 Oak St, Winchester, MA 01890 - Photo 17 84 Oak St, Winchester, MA 01890 - Photo 18 84 Oak St, Winchester, MA 01890 - Photo 19 84 Oak St, Winchester, MA 01890 - Photo 20 84 Oak St, Winchester, MA 01890 - Photo 21 84 Oak St, Winchester, MA 01890 - Photo 22 84 Oak St, Winchester, MA 01890 - Photo 23 84 Oak St, Winchester, MA 01890 - Photo 24 84 Oak St, Winchester, MA 01890 - Photo 25 84 Oak St, Winchester, MA 01890 - Photo 26 84 Oak St, Winchester, MA 01890 - Photo 27 84 Oak St, Winchester, MA 01890 - Photo 28 84 Oak St, Winchester, MA 01890 - Photo 29 84 Oak St, Winchester, MA 01890 - Photo 30 84 Oak St, Winchester, MA 01890 - Photo 31 84 Oak St, Winchester, MA 01890 - Photo 32 84 Oak St, Winchester, MA 01890 - Photo 33 84 Oak St, Winchester, MA 01890 - Photo 34 84 Oak St, Winchester, MA 01890 - Photo 35 84 Oak St, Winchester, MA 01890 - Photo 36 84 Oak St, Winchester, MA 01890 - Photo 37 84 Oak St, Winchester, MA 01890 - Photo 38

      1/38

      84 Oak St  Winchester, MA 01890

      $900,000
      • Single Family
      • Active
      • MLS # 73542597
      • Updated 2 days ago
      • 4
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 2,083
        Sq. Ft.

      Use previous and next buttons to navigate

      423 Washington St, Winchester, MA 01890 - Photo 1 423 Washington St, Winchester, MA 01890 - Photo 2 423 Washington St, Winchester, MA 01890 - Photo 3 423 Washington St, Winchester, MA 01890 - Photo 4 423 Washington St, Winchester, MA 01890 - Photo 5 423 Washington St, Winchester, MA 01890 - Photo 6 423 Washington St, Winchester, MA 01890 - Photo 7 423 Washington St, Winchester, MA 01890 - Photo 8 423 Washington St, Winchester, MA 01890 - Photo 9 423 Washington St, Winchester, MA 01890 - Photo 10 423 Washington St, Winchester, MA 01890 - Photo 11 423 Washington St, Winchester, MA 01890 - Photo 12 423 Washington St, Winchester, MA 01890 - Photo 13 423 Washington St, Winchester, MA 01890 - Photo 14 423 Washington St, Winchester, MA 01890 - Photo 15 423 Washington St, Winchester, MA 01890 - Photo 16 423 Washington St, Winchester, MA 01890 - Photo 17 423 Washington St, Winchester, MA 01890 - Photo 18 423 Washington St, Winchester, MA 01890 - Photo 19 423 Washington St, Winchester, MA 01890 - Photo 20 423 Washington St, Winchester, MA 01890 - Photo 21 423 Washington St, Winchester, MA 01890 - Photo 22 423 Washington St, Winchester, MA 01890 - Photo 23 423 Washington St, Winchester, MA 01890 - Photo 24 423 Washington St, Winchester, MA 01890 - Photo 25 423 Washington St, Winchester, MA 01890 - Photo 26 423 Washington St, Winchester, MA 01890 - Photo 27 423 Washington St, Winchester, MA 01890 - Photo 28 423 Washington St, Winchester, MA 01890 - Photo 29 423 Washington St, Winchester, MA 01890 - Photo 30 423 Washington St, Winchester, MA 01890 - Photo 31 423 Washington St, Winchester, MA 01890 - Photo 32 423 Washington St, Winchester, MA 01890 - Photo 33 423 Washington St, Winchester, MA 01890 - Photo 34 423 Washington St, Winchester, MA 01890 - Photo 35 423 Washington St, Winchester, MA 01890 - Photo 36 423 Washington St, Winchester, MA 01890 - Photo 37 423 Washington St, Winchester, MA 01890 - Photo 38 423 Washington St, Winchester, MA 01890 - Photo 39 423 Washington St, Winchester, MA 01890 - Photo 40 423 Washington St, Winchester, MA 01890 - Photo 41 423 Washington St, Winchester, MA 01890 - Photo 42

      1/42

      423 Washington St  Winchester, MA 01890

      $1,350,000
      • Single Family
      • Active
      • MLS # 73541775
      • 4
        Beds
      • 3
        Full Baths
      • 3
        Total Baths
      • 2,690
        Sq. Ft.
      • 2
        Car Garage

      Use previous and next buttons to navigate

      14 Hillside Ave, Winchester, MA 01890 - Photo 1 14 Hillside Ave, Winchester, MA 01890 - Photo 2 14 Hillside Ave, Winchester, MA 01890 - Photo 3 14 Hillside Ave, Winchester, MA 01890 - Photo 4 14 Hillside Ave, Winchester, MA 01890 - Photo 5 14 Hillside Ave, Winchester, MA 01890 - Photo 6 14 Hillside Ave, Winchester, MA 01890 - Photo 7 14 Hillside Ave, Winchester, MA 01890 - Photo 8 14 Hillside Ave, Winchester, MA 01890 - Photo 9 14 Hillside Ave, Winchester, MA 01890 - Photo 10 14 Hillside Ave, Winchester, MA 01890 - Photo 11 14 Hillside Ave, Winchester, MA 01890 - Photo 12 14 Hillside Ave, Winchester, MA 01890 - Photo 13 14 Hillside Ave, Winchester, MA 01890 - Photo 14 14 Hillside Ave, Winchester, MA 01890 - Photo 15 14 Hillside Ave, Winchester, MA 01890 - Photo 16 14 Hillside Ave, Winchester, MA 01890 - Photo 17 14 Hillside Ave, Winchester, MA 01890 - Photo 18 14 Hillside Ave, Winchester, MA 01890 - Photo 19 14 Hillside Ave, Winchester, MA 01890 - Photo 20 14 Hillside Ave, Winchester, MA 01890 - Photo 21 14 Hillside Ave, Winchester, MA 01890 - Photo 22 14 Hillside Ave, Winchester, MA 01890 - Photo 23 14 Hillside Ave, Winchester, MA 01890 - Photo 24 14 Hillside Ave, Winchester, MA 01890 - Photo 25 14 Hillside Ave, Winchester, MA 01890 - Photo 26 14 Hillside Ave, Winchester, MA 01890 - Photo 27 14 Hillside Ave, Winchester, MA 01890 - Photo 28 14 Hillside Ave, Winchester, MA 01890 - Photo 29 14 Hillside Ave, Winchester, MA 01890 - Photo 30 14 Hillside Ave, Winchester, MA 01890 - Photo 31 14 Hillside Ave, Winchester, MA 01890 - Photo 32 14 Hillside Ave, Winchester, MA 01890 - Photo 33 14 Hillside Ave, Winchester, MA 01890 - Photo 34 14 Hillside Ave, Winchester, MA 01890 - Photo 35 14 Hillside Ave, Winchester, MA 01890 - Photo 36 14 Hillside Ave, Winchester, MA 01890 - Photo 37 14 Hillside Ave, Winchester, MA 01890 - Photo 38 14 Hillside Ave, Winchester, MA 01890 - Photo 39 14 Hillside Ave, Winchester, MA 01890 - Photo 40

      1/40

      Open House
      Sun7/1912-1:30

      14 Hillside Ave  Winchester, MA 01890

      $2,380,000
      • Single Family
      • Active
      • MLS # 73541163
      • 4
        Beds
      • 4
        Full Baths
      • 1
        Partial Bath
      • 5
        Total Baths
      • 3,881
        Sq. Ft.
      • 1
        Car Garage

      Use previous and next buttons to navigate

      258 Cross St, Winchester, MA 01890 - Photo 1 258 Cross St, Winchester, MA 01890 - Photo 2 258 Cross St, Winchester, MA 01890 - Photo 3 258 Cross St, Winchester, MA 01890 - Photo 4 258 Cross St, Winchester, MA 01890 - Photo 5 258 Cross St, Winchester, MA 01890 - Photo 6 258 Cross St, Winchester, MA 01890 - Photo 7 258 Cross St, Winchester, MA 01890 - Photo 8 258 Cross St, Winchester, MA 01890 - Photo 9 258 Cross St, Winchester, MA 01890 - Photo 10 258 Cross St, Winchester, MA 01890 - Photo 11 258 Cross St, Winchester, MA 01890 - Photo 12 258 Cross St, Winchester, MA 01890 - Photo 13 258 Cross St, Winchester, MA 01890 - Photo 14 258 Cross St, Winchester, MA 01890 - Photo 15 258 Cross St, Winchester, MA 01890 - Photo 16 258 Cross St, Winchester, MA 01890 - Photo 17 258 Cross St, Winchester, MA 01890 - Photo 18 258 Cross St, Winchester, MA 01890 - Photo 19 258 Cross St, Winchester, MA 01890 - Photo 20 258 Cross St, Winchester, MA 01890 - Photo 21 258 Cross St, Winchester, MA 01890 - Photo 22 258 Cross St, Winchester, MA 01890 - Photo 23 258 Cross St, Winchester, MA 01890 - Photo 24 258 Cross St, Winchester, MA 01890 - Photo 25 258 Cross St, Winchester, MA 01890 - Photo 26 258 Cross St, Winchester, MA 01890 - Photo 27 258 Cross St, Winchester, MA 01890 - Photo 28 258 Cross St, Winchester, MA 01890 - Photo 29 258 Cross St, Winchester, MA 01890 - Photo 30 258 Cross St, Winchester, MA 01890 - Photo 31 258 Cross St, Winchester, MA 01890 - Photo 32 258 Cross St, Winchester, MA 01890 - Photo 33 258 Cross St, Winchester, MA 01890 - Photo 34 258 Cross St, Winchester, MA 01890 - Photo 35 258 Cross St, Winchester, MA 01890 - Photo 36 258 Cross St, Winchester, MA 01890 - Photo 37 258 Cross St, Winchester, MA 01890 - Photo 38 258 Cross St, Winchester, MA 01890 - Photo 39 258 Cross St, Winchester, MA 01890 - Photo 40

      1/40

      258 Cross St  Winchester, MA 01890

      $999,900
      • Single Family
      • Active
      • MLS # 73541288
      • Updated 7 days ago
      • 4
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,719
        Sq. Ft.

      Use previous and next buttons to navigate

      150 Cambridge St, Winchester, MA 01890 - Photo 1 150 Cambridge St, Winchester, MA 01890 - Photo 2 150 Cambridge St, Winchester, MA 01890 - Photo 3 150 Cambridge St, Winchester, MA 01890 - Photo 4 150 Cambridge St, Winchester, MA 01890 - Photo 5 150 Cambridge St, Winchester, MA 01890 - Photo 6 150 Cambridge St, Winchester, MA 01890 - Photo 7 150 Cambridge St, Winchester, MA 01890 - Photo 8 150 Cambridge St, Winchester, MA 01890 - Photo 9 150 Cambridge St, Winchester, MA 01890 - Photo 10 150 Cambridge St, Winchester, MA 01890 - Photo 11 150 Cambridge St, Winchester, MA 01890 - Photo 12 150 Cambridge St, Winchester, MA 01890 - Photo 13 150 Cambridge St, Winchester, MA 01890 - Photo 14 150 Cambridge St, Winchester, MA 01890 - Photo 15 150 Cambridge St, Winchester, MA 01890 - Photo 16 150 Cambridge St, Winchester, MA 01890 - Photo 17 150 Cambridge St, Winchester, MA 01890 - Photo 18 150 Cambridge St, Winchester, MA 01890 - Photo 19 150 Cambridge St, Winchester, MA 01890 - Photo 20 150 Cambridge St, Winchester, MA 01890 - Photo 21 150 Cambridge St, Winchester, MA 01890 - Photo 22 150 Cambridge St, Winchester, MA 01890 - Photo 23 150 Cambridge St, Winchester, MA 01890 - Photo 24 150 Cambridge St, Winchester, MA 01890 - Photo 25 150 Cambridge St, Winchester, MA 01890 - Photo 26 150 Cambridge St, Winchester, MA 01890 - Photo 27 150 Cambridge St, Winchester, MA 01890 - Photo 28 150 Cambridge St, Winchester, MA 01890 - Photo 29 150 Cambridge St, Winchester, MA 01890 - Photo 30 150 Cambridge St, Winchester, MA 01890 - Photo 31 150 Cambridge St, Winchester, MA 01890 - Photo 32 150 Cambridge St, Winchester, MA 01890 - Photo 33 150 Cambridge St, Winchester, MA 01890 - Photo 34 150 Cambridge St, Winchester, MA 01890 - Photo 35 150 Cambridge St, Winchester, MA 01890 - Photo 36 150 Cambridge St, Winchester, MA 01890 - Photo 37 150 Cambridge St, Winchester, MA 01890 - Photo 38 150 Cambridge St, Winchester, MA 01890 - Photo 39 150 Cambridge St, Winchester, MA 01890 - Photo 40 150 Cambridge St, Winchester, MA 01890 - Photo 41 150 Cambridge St, Winchester, MA 01890 - Photo 42

      1/42

      Open House
      Sun7/1912-2

      150 Cambridge St  Winchester, MA 01890

      $1,099,000
      • Single Family
      • Active
      • MLS # 73530959
      • Updated 2 hours ago
      • 3
        Beds
      • 1
        Full Bath
      • 1
        Partial Bath
      • 2
        Total Baths
      • 1,711
        Sq. Ft.
      • 2
        Car Garage

      Use previous and next buttons to navigate

      26 N Gateway, Winchester, MA 01890 - Photo 1 26 N Gateway, Winchester, MA 01890 - Photo 2 26 N Gateway, Winchester, MA 01890 - Photo 3 26 N Gateway, Winchester, MA 01890 - Photo 4 26 N Gateway, Winchester, MA 01890 - Photo 5 26 N Gateway, Winchester, MA 01890 - Photo 6 26 N Gateway, Winchester, MA 01890 - Photo 7 26 N Gateway, Winchester, MA 01890 - Photo 8 26 N Gateway, Winchester, MA 01890 - Photo 9 26 N Gateway, Winchester, MA 01890 - Photo 10 26 N Gateway, Winchester, MA 01890 - Photo 11 26 N Gateway, Winchester, MA 01890 - Photo 12 26 N Gateway, Winchester, MA 01890 - Photo 13 26 N Gateway, Winchester, MA 01890 - Photo 14 26 N Gateway, Winchester, MA 01890 - Photo 15 26 N Gateway, Winchester, MA 01890 - Photo 16 26 N Gateway, Winchester, MA 01890 - Photo 17 26 N Gateway, Winchester, MA 01890 - Photo 18 26 N Gateway, Winchester, MA 01890 - Photo 19 26 N Gateway, Winchester, MA 01890 - Photo 20 26 N Gateway, Winchester, MA 01890 - Photo 21 26 N Gateway, Winchester, MA 01890 - Photo 22 26 N Gateway, Winchester, MA 01890 - Photo 23 26 N Gateway, Winchester, MA 01890 - Photo 24 26 N Gateway, Winchester, MA 01890 - Photo 25 26 N Gateway, Winchester, MA 01890 - Photo 26 26 N Gateway, Winchester, MA 01890 - Photo 27 26 N Gateway, Winchester, MA 01890 - Photo 28 26 N Gateway, Winchester, MA 01890 - Photo 29 26 N Gateway, Winchester, MA 01890 - Photo 30 26 N Gateway, Winchester, MA 01890 - Photo 31 26 N Gateway, Winchester, MA 01890 - Photo 32 26 N Gateway, Winchester, MA 01890 - Photo 33 26 N Gateway, Winchester, MA 01890 - Photo 34 26 N Gateway, Winchester, MA 01890 - Photo 35 26 N Gateway, Winchester, MA 01890 - Photo 36

      1/36

      Open House
      Sat7/1811-12

      26 N Gateway  Winchester, MA 01890

      $2,149,000
      • Single Family
      • Active
      • MLS # 73538052
      • Updated 6 days ago
      • 4
        Beds
      • 3
        Full Baths
      • 1
        Partial Bath
      • 4
        Total Baths
      • 3,210
        Sq. Ft.
      • 1
        Car Garage

      Use previous and next buttons to navigate

      117 Highland Ave, Winchester, MA 01890 - Photo 1 117 Highland Ave, Winchester, MA 01890 - Photo 2 117 Highland Ave, Winchester, MA 01890 - Photo 3 117 Highland Ave, Winchester, MA 01890 - Photo 4 117 Highland Ave, Winchester, MA 01890 - Photo 5 117 Highland Ave, Winchester, MA 01890 - Photo 6 117 Highland Ave, Winchester, MA 01890 - Photo 7 117 Highland Ave, Winchester, MA 01890 - Photo 8 117 Highland Ave, Winchester, MA 01890 - Photo 9 117 Highland Ave, Winchester, MA 01890 - Photo 10 117 Highland Ave, Winchester, MA 01890 - Photo 11 117 Highland Ave, Winchester, MA 01890 - Photo 12 117 Highland Ave, Winchester, MA 01890 - Photo 13 117 Highland Ave, Winchester, MA 01890 - Photo 14 117 Highland Ave, Winchester, MA 01890 - Photo 15 117 Highland Ave, Winchester, MA 01890 - Photo 16 117 Highland Ave, Winchester, MA 01890 - Photo 17 117 Highland Ave, Winchester, MA 01890 - Photo 18 117 Highland Ave, Winchester, MA 01890 - Photo 19 117 Highland Ave, Winchester, MA 01890 - Photo 20 117 Highland Ave, Winchester, MA 01890 - Photo 21 117 Highland Ave, Winchester, MA 01890 - Photo 22 117 Highland Ave, Winchester, MA 01890 - Photo 23 117 Highland Ave, Winchester, MA 01890 - Photo 24 117 Highland Ave, Winchester, MA 01890 - Photo 25 117 Highland Ave, Winchester, MA 01890 - Photo 26 117 Highland Ave, Winchester, MA 01890 - Photo 27 117 Highland Ave, Winchester, MA 01890 - Photo 28 117 Highland Ave, Winchester, MA 01890 - Photo 29 117 Highland Ave, Winchester, MA 01890 - Photo 30 117 Highland Ave, Winchester, MA 01890 - Photo 31 117 Highland Ave, Winchester, MA 01890 - Photo 32 117 Highland Ave, Winchester, MA 01890 - Photo 33 117 Highland Ave, Winchester, MA 01890 - Photo 34 117 Highland Ave, Winchester, MA 01890 - Photo 35 117 Highland Ave, Winchester, MA 01890 - Photo 36 117 Highland Ave, Winchester, MA 01890 - Photo 37 117 Highland Ave, Winchester, MA 01890 - Photo 38 117 Highland Ave, Winchester, MA 01890 - Photo 39 117 Highland Ave, Winchester, MA 01890 - Photo 40

      1/40

      Open House
      Sun7/1912-1:30

      117 Highland Ave  Winchester, MA 01890

      $1,725,000
      • Single Family
      • Active
      • MLS # 73538393
      • Updated 7 days ago
      • 5
        Beds
      • 3
        Full Baths
      • 1
        Partial Bath
      • 4
        Total Baths
      • 3,722
        Sq. Ft.
      • 2
        Car Garage

      Use previous and next buttons to navigate

      15 Fieldstone Dr, Winchester, MA 01890 - Photo 1 15 Fieldstone Dr, Winchester, MA 01890 - Photo 2 15 Fieldstone Dr, Winchester, MA 01890 - Photo 3 15 Fieldstone Dr, Winchester, MA 01890 - Photo 4 15 Fieldstone Dr, Winchester, MA 01890 - Photo 5 15 Fieldstone Dr, Winchester, MA 01890 - Photo 6 15 Fieldstone Dr, Winchester, MA 01890 - Photo 7 15 Fieldstone Dr, Winchester, MA 01890 - Photo 8 15 Fieldstone Dr, Winchester, MA 01890 - Photo 9 15 Fieldstone Dr, Winchester, MA 01890 - Photo 10 15 Fieldstone Dr, Winchester, MA 01890 - Photo 11 15 Fieldstone Dr, Winchester, MA 01890 - Photo 12 15 Fieldstone Dr, Winchester, MA 01890 - Photo 13 15 Fieldstone Dr, Winchester, MA 01890 - Photo 14 15 Fieldstone Dr, Winchester, MA 01890 - Photo 15 15 Fieldstone Dr, Winchester, MA 01890 - Photo 16 15 Fieldstone Dr, Winchester, MA 01890 - Photo 17 15 Fieldstone Dr, Winchester, MA 01890 - Photo 18 15 Fieldstone Dr, Winchester, MA 01890 - Photo 19 15 Fieldstone Dr, Winchester, MA 01890 - Photo 20 15 Fieldstone Dr, Winchester, MA 01890 - Photo 21 15 Fieldstone Dr, Winchester, MA 01890 - Photo 22 15 Fieldstone Dr, Winchester, MA 01890 - Photo 23 15 Fieldstone Dr, Winchester, MA 01890 - Photo 24 15 Fieldstone Dr, Winchester, MA 01890 - Photo 25 15 Fieldstone Dr, Winchester, MA 01890 - Photo 26 15 Fieldstone Dr, Winchester, MA 01890 - Photo 27 15 Fieldstone Dr, Winchester, MA 01890 - Photo 28 15 Fieldstone Dr, Winchester, MA 01890 - Photo 29 15 Fieldstone Dr, Winchester, MA 01890 - Photo 30 15 Fieldstone Dr, Winchester, MA 01890 - Photo 31 15 Fieldstone Dr, Winchester, MA 01890 - Photo 32 15 Fieldstone Dr, Winchester, MA 01890 - Photo 33 15 Fieldstone Dr, Winchester, MA 01890 - Photo 34 15 Fieldstone Dr, Winchester, MA 01890 - Photo 35 15 Fieldstone Dr, Winchester, MA 01890 - Photo 36 15 Fieldstone Dr, Winchester, MA 01890 - Photo 37 15 Fieldstone Dr, Winchester, MA 01890 - Photo 38 15 Fieldstone Dr, Winchester, MA 01890 - Photo 39 15 Fieldstone Dr, Winchester, MA 01890 - Photo 40 15 Fieldstone Dr, Winchester, MA 01890 - Photo 41 15 Fieldstone Dr, Winchester, MA 01890 - Photo 42
      Price Reduced

      1/42

      Open House
      Sun7/1911:30-1

      15 Fieldstone Dr  Winchester, MA 01890

      $1,975,000
      -$24,900 (-1.25%)
      • Single Family
      • Active
      • MLS # 73537676
      • Updated 2 days ago
      • 4
        Beds
      • 3
        Full Baths
      • 1
        Partial Bath
      • 4
        Total Baths
      • 3,286
        Sq. Ft.
      • 2
        Car Garage

      Use previous and next buttons to navigate

      38 Robinhood Rd, Winchester, MA 01890 - Photo 1 38 Robinhood Rd, Winchester, MA 01890 - Photo 2 38 Robinhood Rd, Winchester, MA 01890 - Photo 3 38 Robinhood Rd, Winchester, MA 01890 - Photo 4 38 Robinhood Rd, Winchester, MA 01890 - Photo 5 38 Robinhood Rd, Winchester, MA 01890 - Photo 6 38 Robinhood Rd, Winchester, MA 01890 - Photo 7 38 Robinhood Rd, Winchester, MA 01890 - Photo 8 38 Robinhood Rd, Winchester, MA 01890 - Photo 9 38 Robinhood Rd, Winchester, MA 01890 - Photo 10 38 Robinhood Rd, Winchester, MA 01890 - Photo 11 38 Robinhood Rd, Winchester, MA 01890 - Photo 12 38 Robinhood Rd, Winchester, MA 01890 - Photo 13 38 Robinhood Rd, Winchester, MA 01890 - Photo 14 38 Robinhood Rd, Winchester, MA 01890 - Photo 15 38 Robinhood Rd, Winchester, MA 01890 - Photo 16 38 Robinhood Rd, Winchester, MA 01890 - Photo 17 38 Robinhood Rd, Winchester, MA 01890 - Photo 18 38 Robinhood Rd, Winchester, MA 01890 - Photo 19 38 Robinhood Rd, Winchester, MA 01890 - Photo 20 38 Robinhood Rd, Winchester, MA 01890 - Photo 21 38 Robinhood Rd, Winchester, MA 01890 - Photo 22 38 Robinhood Rd, Winchester, MA 01890 - Photo 23 38 Robinhood Rd, Winchester, MA 01890 - Photo 24 38 Robinhood Rd, Winchester, MA 01890 - Photo 25 38 Robinhood Rd, Winchester, MA 01890 - Photo 26 38 Robinhood Rd, Winchester, MA 01890 - Photo 27 38 Robinhood Rd, Winchester, MA 01890 - Photo 28 38 Robinhood Rd, Winchester, MA 01890 - Photo 29 38 Robinhood Rd, Winchester, MA 01890 - Photo 30 38 Robinhood Rd, Winchester, MA 01890 - Photo 31 38 Robinhood Rd, Winchester, MA 01890 - Photo 32
      Price Reduced

      1/32

      Open House
      Sun7/191-2:30

      38 Robinhood Rd  Winchester, MA 01890

      $1,175,000
      -$50,000 (-4.08%)
      • Single Family
      • Active
      • MLS # 73537786
      • Updated 1 day ago
      • 3
        Beds
      • 1
        Full Bath
      • 2
        Partial Baths
      • 3
        Total Baths
      • 1,736
        Sq. Ft.
      • 2
        Car Garage

      Use previous and next buttons to navigate

      10 Rangeley Rd, Winchester, MA 01890 - Photo 1 10 Rangeley Rd, Winchester, MA 01890 - Photo 2 10 Rangeley Rd, Winchester, MA 01890 - Photo 3 10 Rangeley Rd, Winchester, MA 01890 - Photo 4 10 Rangeley Rd, Winchester, MA 01890 - Photo 5 10 Rangeley Rd, Winchester, MA 01890 - Photo 6 10 Rangeley Rd, Winchester, MA 01890 - Photo 7 10 Rangeley Rd, Winchester, MA 01890 - Photo 8 10 Rangeley Rd, Winchester, MA 01890 - Photo 9 10 Rangeley Rd, Winchester, MA 01890 - Photo 10 10 Rangeley Rd, Winchester, MA 01890 - Photo 11 10 Rangeley Rd, Winchester, MA 01890 - Photo 12 10 Rangeley Rd, Winchester, MA 01890 - Photo 13 10 Rangeley Rd, Winchester, MA 01890 - Photo 14 10 Rangeley Rd, Winchester, MA 01890 - Photo 15 10 Rangeley Rd, Winchester, MA 01890 - Photo 16 10 Rangeley Rd, Winchester, MA 01890 - Photo 17 10 Rangeley Rd, Winchester, MA 01890 - Photo 18 10 Rangeley Rd, Winchester, MA 01890 - Photo 19 10 Rangeley Rd, Winchester, MA 01890 - Photo 20 10 Rangeley Rd, Winchester, MA 01890 - Photo 21 10 Rangeley Rd, Winchester, MA 01890 - Photo 22 10 Rangeley Rd, Winchester, MA 01890 - Photo 23 10 Rangeley Rd, Winchester, MA 01890 - Photo 24 10 Rangeley Rd, Winchester, MA 01890 - Photo 25 10 Rangeley Rd, Winchester, MA 01890 - Photo 26 10 Rangeley Rd, Winchester, MA 01890 - Photo 27 10 Rangeley Rd, Winchester, MA 01890 - Photo 28 10 Rangeley Rd, Winchester, MA 01890 - Photo 29 10 Rangeley Rd, Winchester, MA 01890 - Photo 30 10 Rangeley Rd, Winchester, MA 01890 - Photo 31 10 Rangeley Rd, Winchester, MA 01890 - Photo 32 10 Rangeley Rd, Winchester, MA 01890 - Photo 33 10 Rangeley Rd, Winchester, MA 01890 - Photo 34 10 Rangeley Rd, Winchester, MA 01890 - Photo 35 10 Rangeley Rd, Winchester, MA 01890 - Photo 36 10 Rangeley Rd, Winchester, MA 01890 - Photo 37 10 Rangeley Rd, Winchester, MA 01890 - Photo 38 10 Rangeley Rd, Winchester, MA 01890 - Photo 39 10 Rangeley Rd, Winchester, MA 01890 - Photo 40 10 Rangeley Rd, Winchester, MA 01890 - Photo 41 10 Rangeley Rd, Winchester, MA 01890 - Photo 42

      1/42

      10 Rangeley Rd  Winchester, MA 01890

      $3,199,000
      • Single Family
      • Active
      • MLS # 73535697
      • 5
        Beds
      • 4
        Full Baths
      • 1
        Partial Bath
      • 5
        Total Baths
      • 5,406
        Sq. Ft.
      • 2
        Car Garage

      Save this searchYou’ll get email updates when new properties matching this criteria go on the market. You can also run these searches quickly under “Properties & Searches” at the top of every page. and receive alerts when new properties are listed.

      Find Real Estate in Winchester Highlands, MA

      Coldwell Banker Realty can help you find Winchester Highlands homes for sale, rentals and open houses. Refine your Winchester Highlands real estate search results by price, property type, bedrooms, baths and other features. Need more information? View our Winchester Highlands real estate offices and let us help you find the perfect property.

      School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

      Assurant Home Warranty logo

      Protect your home and budget from life’s surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans

      Coldwell Banker Realty and Guaranteed Rate Affinity, LLC share common ownership and because of this relationship the brokerage may receive a financial or other benefit. You are not required to use Guaranteed Rate Affinity, LLC as a condition of purchase or sale of any real estate. Operating in the state of New York as GR Affinity, LLC in lieu of the legal name Guaranteed Rate Affinity, LLC.

      Real estate agents affiliated with Coldwell Banker are independent contractor sales associates and are not employees of Coldwell Banker.

      © 2026 Coldwell Banker. All Rights Reserved. Coldwell Banker and the Coldwell Banker logos are trademarks of Coldwell Banker Real Estate LLC. The Coldwell Banker® System is comprised of company owned offices which are owned by a subsidiary of Anywhere Advisors LLC and franchised offices which are independently owned and operated. The Coldwell Banker System fully supports the principles of the Fair Housing Act and the Equal Opportunity Act.

      Search options

      We can’t map any of the properties in your results.