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Winchester Homes for Sale

Winchester Homes for Sale

42 Homes for Sale in Winchester

26 Swan Road 1
42 Photos
$3,989,000
6 Beds 6/1 Baths 8,463 Sqft
26 Swan Road Winchester, MA 01890
Year Built:
2006
HOA:
None
View Details
11 Viking Rd 1
3 Photos
$3,799,900
7 Beds 7/1 Baths 7,429 Sqft
11 Viking Rd Winchester, MA 01890
Year Built:
2025
HOA:
None
View Details
54 Johnson Road 1
42 Photos
$3,699,000
7 Beds 7/1 Baths 7,982 Sqft
54 Johnson Road Winchester, MA 01890
Year Built:
2024
HOA:
None
View Details
20 Amberwood Dr 1
34 Photos
$3,698,000
6 Beds 7 Baths 8,866 Sqft
20 Amberwood Dr Winchester, MA 01890
Year Built:
2024
HOA:
None
View Details
27 Everett Ave 1
41 Photos
$3,599,000
6 Beds 5/1 Baths 7,431 Sqft
27 Everett Ave Winchester, MA 01890
Year Built:
1905
HOA:
None
View Details
21 Sheffield West 1
42 Photos
$3,199,000
6 Beds 3/2 Baths 5,198 Sqft
21 Sheffield West Winchester, MA 01890
Year Built:
1910
HOA:
None
View Details
Open House, Sat 12:00-1:00
10 Sheffield Road 1
40 Photos
$3,149,000
7 Beds 5/1 Baths 6,200 Sqft
10 Sheffield Road Winchester, MA 01890
Year Built:
1916
HOA:
None
View Details
Lot 3 Abby Road 1
13 Photos
$2,999,999
5 Beds 4/1 Baths 5,716 Sqft
Lot 3 Abby Road Winchester, MA 01890
Year Built:
2025
HOA:
None
View Details
8 Chestnut St 1
42 Photos
$2,999,000
5 Beds 4/2 Baths 5,354 Sqft
8 Chestnut St Winchester, MA 01890
Year Built:
1850
HOA:
None
View Details
14 Nassau Drive 1
42 Photos
$2,950,000
6 Beds 5/2 Baths 6,968 Sqft
14 Nassau Drive Winchester, MA 01890
Year Built:
2002
HOA:
None
View Details
NEW CONSTRUCTION
11 Taft Dr 1
5 Photos
$2,899,000
5 Beds 5/1 Baths 4,627 Sqft
11 Taft Dr Winchester, MA 01890
Year Built:
2025
HOA:
None
View Details
Open House, Thu 5:30-6:30
11 Fieldstone Drive 1
41 Photos
$2,899,000
5 Beds 4/1 Baths 6,904 Sqft
11 Fieldstone Drive Winchester, MA 01890
Year Built:
1989
HOA:
None
View Details
8 Tanglewood Lane 1
42 Photos
$2,850,000
4 Beds 3 Baths 4,276 Sqft
8 Tanglewood Lane Winchester, MA 01890
Year Built:
1985
HOA:
None
View Details
18 Middlesex St 1
35 Photos
$2,695,000
4 Beds 4/1 Baths 5,233 Sqft
18 Middlesex St Winchester, MA 01890
Year Built:
2004
HOA:
None
View Details
NEW CONSTRUCTION
Open House, Sat 2:00-3:30
89 Wildwood St 1
9 Photos
$2,599,000
7 Beds 5/1 Baths 4,829 Sqft
89 Wildwood St Winchester, MA 01890
Year Built:
2025
HOA:
None
View Details
15 Churchill Road 1
42 Photos
$2,599,000
4 Beds 4/1 Baths 5,501 Sqft
15 Churchill Road Winchester, MA 01890
Year Built:
2024
HOA:
None
View Details
19 Yale St 1
42 Photos
$2,499,000
6 Beds 3/1 Baths 4,212 Sqft
19 Yale St Winchester, MA 01890
Year Built:
1880
HOA:
None
View Details
9 Prospect St 1
39 Photos
$2,499,000
6 Beds 3/1 Baths 4,667 Sqft
9 Prospect St Winchester, MA 01890
Year Built:
1895
HOA:
None
View Details
17 Wagon Wheel Rd 1
41 Photos
$2,450,000
5 Beds 5 Baths 3,940 Sqft
17 Wagon Wheel Rd Winchester, MA 01890
Year Built:
1983
HOA:
None
View Details
5 Azalea Rd 1
19 Photos
$2,449,000
4 Beds 3/1 Baths 4,959 Sqft
5 Azalea Rd Winchester, MA 01890
Year Built:
1980
HOA:
None
View Details
Open House, Sat 2:00-3:00
276 High Street 1
42 Photos
$2,399,000
5 Beds 3/1 Baths 5,077 Sqft
276 High Street Winchester, MA 01890
Year Built:
1992
HOA:
None
View Details
Open House, Thu 5:30-6:30
17 Harrison Street 1
42 Photos
$2,250,000
5 Beds 3/1 Baths 3,719 Sqft
17 Harrison Street Winchester, MA 01890
Year Built:
1952
HOA:
None
View Details
Open House, Sat 12:30-2:00
5 Squire Rd 1
40 Photos
$2,099,000
6 Beds 3/1 Baths 4,696 Sqft
5 Squire Rd Winchester, MA 01890
Year Built:
2016
HOA:
None
View Details
20 Seneca Road 1
40 Photos
$1,995,000
3 Beds 2 Baths 2,813 Sqft
20 Seneca Road Winchester, MA 01890
Year Built:
1930
HOA:
None
View Details
10 Olde Lyme Road 1
37 Photos
$1,949,000
5 Beds 3/1 Baths 3,478 Sqft
10 Olde Lyme Road Winchester, MA 01890
Year Built:
1960
HOA:
None
View Details
Open House, Sat 11:00-1:00
14 Hillside Ave 1
42 Photos
$1,650,000
3 Beds 2/1 Baths 2,605 Sqft
14 Hillside Ave Winchester, MA 01890
Year Built:
1870
HOA:
None
View Details
Open House, Thu 5:00-6:30
189 Mystic Valley Pkwy 1
35 Photos
$1,599,000
6 Beds 2/1 Baths 3,543 Sqft
189 Mystic Valley Pkwy Winchester, MA 01890
Year Built:
1850
HOA:
None
View Details
Open House, Thu 5:00-7:00
195 Mystic Valley Parkway 1
38 Photos
$1,500,000
4 Beds 1/2 Bath 2,897 Sqft
195 Mystic Valley Parkway Winchester, MA 01890
Year Built:
1934
HOA:
None
View Details
7 Thornberry Road 1
34 Photos
$1,499,900
5 Beds 2 Baths 3,033 Sqft
7 Thornberry Road Winchester, MA 01890
Year Built:
1957
HOA:
None
View Details
19 Cox Road 1
40 Photos
$1,499,000
3 Beds 1/1 Bath 2,351 Sqft
19 Cox Road Winchester, MA 01890
Year Built:
1956
HOA:
None
View Details
Open House, Sat 12:00-1:00
34 Fells Road 1
42 Photos
$1,499,000
3 Beds 2/2 Baths 3,351 Sqft
34 Fells Road Winchester, MA 01890
Year Built:
1946
HOA:
None
View Details
Open House, Thu 5:30-7:00
117 Mount Vernon Street 1
42 Photos
$1,399,000
3 Beds 2/1 Baths 2,141 Sqft
117 Mount Vernon Street Winchester, MA 01890
Year Built:
1880
HOA:
None
View Details
Open House, Fri 11:00-12:00
147 Highland Ave 1
37 Photos
$1,399,000
3 Beds 2 Baths 1,884 Sqft
147 Highland Ave Winchester, MA 01890
Year Built:
1919
HOA:
None
View Details
71 Woodside Rd 1
22 Photos
$1,295,000
4 Beds 1/1 Bath 2,202 Sqft
71 Woodside Rd Winchester, MA 01890
Year Built:
1927
HOA:
None
View Details
61 Westland Avenue 1
16 Photos
$1,199,000
4 Beds 2 Baths 2,621 Sqft
61 Westland Avenue Winchester, MA 01890
Year Built:
1952
HOA:
None
View Details
44 Forest Street 1
42 Photos
$1,199,000
3 Beds 1/1 Bath 1,906 Sqft
44 Forest Street Winchester, MA 01890
Year Built:
1926
HOA:
None
View Details
Open House, Sat 12:00-1:30
10 Allen Rd 1
23 Photos
$1,199,000
3 Beds 1/1 Bath 1,520 Sqft
10 Allen Rd Winchester, MA 01890
Year Built:
1929
HOA:
None
View Details
48 Tremont Street 1
15 Photos
$998,000
4 Beds 3 Baths 2,333 Sqft
48 Tremont Street Winchester, MA 01890
Year Built:
1959
HOA:
None
View Details
Open House, Sat 11:30-1:00
235 Cross Street 1
32 Photos
$749,900
3 Beds 1/1 Bath 1,931 Sqft
235 Cross Street Winchester, MA 01890
Year Built:
1956
HOA:
None
View Details
7 Conant Rd #34 1
36 Photos
$749,900
2 Beds 2 Baths 1,545 Sqft
7 Conant Rd #34 Winchester, MA 01890
Year Built:
1999
HOA:
None
View Details
7 Conant Rd #20 1
37 Photos
$699,900
2 Beds 2 Baths 1,168 Sqft
7 Conant Rd #20 Winchester, MA 01890
Year Built:
2000
HOA:
None
View Details
200 Swanton St #722 1
31 Photos
$385,000
1 Bed 1 Bath 613 Sqft
200 Swanton St #722 Winchester, MA 01890
Year Built:
1966
HOA:
None
View Details

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