48 Homes for Sale in Winchester
$4,250,000
5
Beds
3/1
Baths
4,484
Sqft
9 Lakeview Terrace
Winchester, MA 01890
Year Built:
1905
HOA:
None
$3,999,000
6
Beds
4/1
Baths
6,367
Sqft
40 Foxcroft Rd
Winchester, MA 01890
Year Built:
2025
HOA:
None
$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
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
$3,175,000
5
Beds
4/1
Baths
5,386
Sqft
21 Fernway
Winchester, MA 01890
Year Built:
1963
HOA:
None
$3,099,000
6
Beds
3/1
Baths
5,238
Sqft
54 Wedgemere Avenue
Winchester, MA 01890
Year Built:
1915
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
$2,899,000
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
$2,899,000
7
Beds
5/1
Baths
5,864
Sqft
10 Sheffield Road
Winchester, MA 01890
Year Built:
1916
HOA:
None
$2,890,000
5
Beds
4/2
Baths
5,354
Sqft
8 Chestnut St
Winchester, MA 01890
Year Built:
1850
HOA:
None
$2,850,000
6
Beds
5/2
Baths
6,968
Sqft
14 Nassau Drive
Winchester, MA 01890
Year Built:
2002
HOA:
None
$2,650,000
4
Beds
3
Baths
4,276
Sqft
8 Tanglewood Lane
Winchester, MA 01890
Year Built:
1985
HOA:
None
$2,599,000
4
Beds
4/1
Baths
5,501
Sqft
15 Churchill Road
Winchester, MA 01890
Year Built:
2025
HOA:
None
$2,599,000
6
Beds
4/1
Baths
5,824
Sqft
107 Cambridge Street
Winchester, MA 01890
Year Built:
1911
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
$2,499,000
6
Beds
3/2
Baths
3,728
Sqft
6 Ivy Cir
Winchester, MA 01890
Year Built:
2025
HOA:
None
$2,499,000
7
Beds
5/1
Baths
4,829
Sqft
89 Wildwood St
Winchester, MA 01890
Year Built:
2025
HOA:
None
$2,349,000
4
Beds
3/1
Baths
4,959
Sqft
5 Azalea Rd
Winchester, MA 01890
Year Built:
1980
HOA:
None
$2,299,000
6
Beds
3/1
Baths
4,667
Sqft
9 Prospect St
Winchester, MA 01890
Year Built:
1895
HOA:
None
$2,295,000
6
Beds
5/1
Baths
5,791
Sqft
58 Bacon Street
Winchester, MA 01890
Year Built:
1924
HOA:
None
$2,250,000
5
Beds
5
Baths
5,000
Sqft
1 Fox Hunt Ln
Winchester, MA 01890
Year Built:
1968
HOA:
None
$2,190,000
5
Beds
3/1
Baths
4,378
Sqft
4 Fieldstone Dr
Winchester, MA 01890
Year Built:
1987
HOA:
None
$2,000,000
6
Beds
3/1
Baths
4,696
Sqft
5 Squire Rd
Winchester, MA 01890
Year Built:
2016
HOA:
None
$1,999,000
5
Beds
3/1
Baths
3,874
Sqft
4 Worthen Road
Winchester, MA 01890
Year Built:
1932
HOA:
None
$1,799,999
3
Beds
2/1
Baths
3,002
Sqft
44 Amberwood Drive
Winchester, MA 01890
Year Built:
1983
HOA:
None
$1,699,000
5
Beds
4
Baths
2,853
Sqft
32 Oneida Road
Winchester, MA 01890
Year Built:
1930
HOA:
None
$1,499,000
3
Beds
2/1
Baths
2,605
Sqft
14 Hillside Ave
Winchester, MA 01890
Year Built:
1870
HOA:
None
$1,449,900
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
$1,349,000
3
Beds
1/1
Bath
3,335
Sqft
10 Girard Rd
Winchester, MA 01890
Year Built:
1953
HOA:
None
$1,345,000
3
Beds
2
Baths
2,238
Sqft
49 Lincoln Street
Winchester, MA 01890
Year Built:
1905
HOA:
None
$1,329,000
3
Beds
2
Baths
1,884
Sqft
147 Highland Ave
Winchester, MA 01890
Year Built:
1919
HOA:
None
$1,299,000
3
Beds
3/1
Baths
2,136
Sqft
162 Swanton Street #162
Winchester, MA 01890
Year Built:
2025
HOA:
None
$1,295,000
4
Beds
1/1
Bath
2,202
Sqft
71 Woodside Rd
Winchester, MA 01890
Year Built:
1927
HOA:
None
$1,199,900
4
Beds
2/1
Baths
2,302
Sqft
518 Washington St
Winchester, MA 01890
Year Built:
1915
HOA:
None
$1,099,000
3
Beds
2
Baths
1,536
Sqft
8 Garfield Avenue
Winchester, MA 01890
Year Built:
1940
HOA:
None
$959,000
3
Beds
1
Bath
1,425
Sqft
571 Washington St
Winchester, MA 01890
Year Built:
1920
HOA:
None
$859,000
2
Beds
1
Bath
1,123
Sqft
22 Grove Place #4
Winchester, MA 01890
Year Built:
1986
HOA:
None
$799,900
3
Beds
2
Baths
1,441
Sqft
9 Emerson Ct
Winchester, MA 01890
Year Built:
1901
HOA:
None
$679,900
2
Beds
2
Baths
1,168
Sqft
7 Conant Rd #20
Winchester, MA 01890
Year Built:
2000
HOA:
None
$674,900
2
Beds
1
Bath
1,084
Sqft
20 Arthur St #20
Winchester, MA 01890
Year Built:
1897
HOA:
None
$625,000
2
Beds
1/1
Bath
1,554
Sqft
50 Lake St #B
Winchester, MA 01890
Year Built:
1976
HOA:
None
Showing 1 - 48 of 48 Results
Listing Saved!
Get alerts on new listings and listing updates that match below search criteria
Add to Collection
Organize and manage your saved listings by addint it to a collection
