
35 Homes for Sale in Winchester
$3,999,000
6
Beds
4/1
Baths
6,367
Sqft
40 Foxcroft Road
Winchester, MA 01890
Year Built:
2025
HOA:
None
$3,989,000
6
Beds
7/1
Baths
7,330
Sqft
6 Ledgewood Road
Winchester, MA 01890
Year Built:
2019
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
$3,600,000
6
Beds
7/1
Baths
8,866
Sqft
20 Amberwood Dr
Winchester, MA 01890
Year Built:
2024
HOA:
None
$3,599,000
6
Beds
4/1
Baths
5,876
Sqft
5 Stratford Road
Winchester, MA 01890
Year Built:
1870
HOA:
None
$3,475,000
5
Beds
3/1
Baths
5,632
Sqft
80 Arlington Street
Winchester, MA 01890
Year Built:
1973
HOA:
None
$3,249,000
6
Beds
6/1
Baths
6,028
Sqft
44 Cabot Street
Winchester, MA 01890
Year Built:
2025
HOA:
None
$3,199,000
6
Beds
6/1
Baths
8,463
Sqft
26 Swan Road
Winchester, MA 01890
Year Built:
2006
HOA:
None
$2,849,000
5
Beds
5/1
Baths
4,627
Sqft
11 Taft Ln
Winchester, MA 01890
Year Built:
2025
HOA:
None
$2,750,000
5
Beds
3/1
Baths
4,779
Sqft
48 Salisbury Street
Winchester, MA 01890
Year Built:
1938
HOA:
None
$2,689,000
6
Beds
5/1
Baths
4,563
Sqft
382 S Border Rd
Winchester, MA 01890
Year Built:
2025
HOA:
None
$2,550,000
5
Beds
4/1
Baths
3,800
Sqft
19 Laurel Hill Ln
Winchester, MA 01890
Year Built:
1954
HOA:
None
$2,399,000
7
Beds
5/1
Baths
4,829
Sqft
89 Wildwood St
Winchester, MA 01890
Year Built:
2025
HOA:
None
$2,350,000
5
Beds
3/1
Baths
5,006
Sqft
276 High Street
Winchester, MA 01890
Year Built:
1992
HOA:
None
$2,299,900
6
Beds
4
Baths
4,385
Sqft
5 Bacon St
Winchester, MA 01890
Year Built:
1910
HOA:
None
$2,239,000
5
Beds
4/1
Baths
4,798
Sqft
61 Grove Street
Winchester, MA 01890
Year Built:
2017
HOA:
None
$2,199,000
5
Beds
3/1
Baths
6,232
Sqft
5 Azalea Rd
Winchester, MA 01890
Year Built:
1980
HOA:
None
$2,195,000
6
Beds
5/1
Baths
5,791
Sqft
58 Bacon Street
Winchester, MA 01890
Year Built:
1924
HOA:
None
$2,099,000
6
Beds
3/1
Baths
3,521
Sqft
19 Glengarry Road
Winchester, MA 01890
Year Built:
1897
HOA:
None
$1,990,000
4
Beds
4/1
Baths
4,474
Sqft
4 Chestnut St
Winchester, MA 01890
Year Built:
1959
HOA:
None
$1,900,000
4
Beds
3/2
Baths
5,361
Sqft
4 Aricia Ln
Winchester, MA 01890
Year Built:
1984
HOA:
None
$1,879,000
5
Beds
3/1
Baths
3,294
Sqft
20 Grove Pl
Winchester, MA 01890
Year Built:
1910
HOA:
None
$1,500,000
4
Beds
2/1
Baths
2,765
Sqft
7 Sherman Place #7
Winchester, MA 01890
Year Built:
2005
HOA:
None
$1,500,000
4
Beds
2/1
Baths
2,765
Sqft
7 Sherman Place #7
Winchester, MA 01890
Year Built:
2005
HOA:
None
$1,399,000
3
Beds
4/1
Baths
2,722
Sqft
6 Wyman Court #6
Winchester, MA 01890
Year Built:
2025
HOA:
None
$1,379,000
5
Beds
2
Baths
3,033
Sqft
7 Thornberry Road
Winchester, MA 01890
Year Built:
1957
HOA:
None
$1,349,900
5
Beds
2
Baths
1,706
Sqft
35 Harvard Street
Winchester, MA 01890
Year Built:
1880
HOA:
None
$1,275,000
3
Beds
3/1
Baths
2,459
Sqft
162 Swanton Street #162
Winchester, MA 01890
Year Built:
2025
HOA:
None
$1,275,000
3
Beds
3/1
Baths
2,459
Sqft
162 Swanton Street #162
Winchester, MA 01890
Year Built:
2025
HOA:
None
$1,249,900
3
Beds
2/1
Baths
2,458
Sqft
59 Johnson Rd
Winchester, MA 01890
Year Built:
1958
HOA:
None
$1,049,000
2
Beds
2
Baths
1,296
Sqft
36 Elmwood Ave #4
Winchester, MA 01890
Year Built:
2021
HOA:
None
$799,900
2
Beds
2
Baths
1,545
Sqft
62 Vine Street #62
Winchester, MA 01890
Year Built:
1982
HOA:
None
$662,500
3
Beds
2
Baths
1,232
Sqft
2 George Road #2
Winchester, MA 01890
Year Built:
1962
HOA:
None
$650,000
3
Beds
2/1
Baths
1,824
Sqft
171 Swanton St #60
Winchester, MA 01890
Year Built:
1985
HOA:
None
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