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