74 Homes for Sale in Winchester
$4,174,000
7
Beds
3/3
Baths
7,043
Sqft
2 Everett Ave
Winchester, MA 01890
Year Built:
1916
HOA:
None
$3,989,000
6
Beds
7/1
Baths
7,330
Sqft
6 Ledgewood Road
Winchester, MA 01890
Year Built:
2019
HOA:
None
$3,899,000
6
Beds
4/1
Baths
6,367
Sqft
40 Foxcroft Road
Winchester, MA 01890
Year Built:
2025
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
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
$3,499,000
5
Beds
5/2
Baths
7,101
Sqft
257 High Street
Winchester, MA 01890
Year Built:
1994
HOA:
None
$3,199,000
6
Beds
6/1
Baths
8,463
Sqft
26 Swan Road
Winchester, MA 01890
Year Built:
2006
HOA:
None
$3,099,000
6
Beds
6/1
Baths
6,028
Sqft
44 Cabot Street
Winchester, MA 01890
Year Built:
2025
HOA:
None
$2,999,999
5
Beds
4/1
Baths
5,716
Sqft
6 Abby Road
Winchester, MA 01890
Year Built:
2025
HOA:
None
$2,975,000
6
Beds
3/1
Baths
5,238
Sqft
54 Wedgemere Avenue
Winchester, MA 01890
Year Built:
1915
HOA:
None
$2,849,000
5
Beds
5/1
Baths
4,627
Sqft
11 Taft Ln
Winchester, MA 01890
Year Built:
2025
HOA:
None
$2,799,000
7
Beds
5/1
Baths
5,864
Sqft
10 Sheffield Road
Winchester, MA 01890
Year Built:
1916
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 Road
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
$2,399,000
6
Beds
4/1
Baths
4,200
Sqft
14 Grant Rd
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
$2,245,000
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
$2,049,000
4
Beds
3/2
Baths
3,716
Sqft
64 Westland Ave
Winchester, MA 01890
Year Built:
1931
HOA:
None
$2,000,000
6
Beds
3/1
Baths
4,696
Sqft
5 Squire Rd
Winchester, MA 01890
Year Built:
2016
HOA:
None
$1,990,000
4
Beds
4/1
Baths
4,474
Sqft
4 Chestnut St
Winchester, MA 01890
Year Built:
1959
HOA:
None
$1,950,000
4
Beds
4/1
Baths
3,512
Sqft
7 Wainwright Rd #72
Winchester, MA 01890
Year Built:
1989
HOA:
None
$1,900,000
4
Beds
3/2
Baths
5,361
Sqft
4 Aricia Ln
Winchester, MA 01890
Year Built:
1984
HOA:
None
$1,649,000
5
Beds
3/2
Baths
3,508
Sqft
166 Forest St
Winchester, MA 01890
Year Built:
2002
HOA:
None
$1,599,000
3
Beds
2
Baths
2,368
Sqft
4 Oakland Cir
Winchester, MA 01890
Year Built:
1951
HOA:
None
$1,599,000
5
Beds
3/1
Baths
2,718
Sqft
77 Washington St
Winchester, MA 01890
Year Built:
1910
HOA:
None
$1,550,000
5
Beds
3
Baths
2,995
Sqft
205 Ridge St
Winchester, MA 01890
Year Built:
1960
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
4
Beds
4/1
Baths
2,500
Sqft
4 Wyman Court #4
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
$1,125,000
3
Beds
2/1
Baths
2,648
Sqft
89 Main St
Winchester, MA 01890
Year Built:
1932
HOA:
None
$1,050,000
4
Beds
2
Baths
1,938
Sqft
380 Cross St
Winchester, MA 01890
Year Built:
1939
HOA:
None
$999,999
3
Beds
2
Baths
1,535
Sqft
16 Park Ave #1
Winchester, MA 01890
Year Built:
1915
HOA:
None
$959,000
3
Beds
1
Bath
1,425
Sqft
571 Washington St
Winchester, MA 01890
Year Built:
1920
HOA:
None
$662,500
3
Beds
2
Baths
1,232
Sqft
2 George Road #2
Winchester, MA 01890
Year Built:
1962
HOA:
None
$409,900
1
Bed
1
Bath
634
Sqft
200 Swanton St #T11
Winchester, MA 01890
Year Built:
1966
HOA:
None
$399,900
2
Beds
1
Bath
1,084
Sqft
20 Arthur St #20
Winchester, MA 01890
Year Built:
1897
HOA:
None
$13,500/mo
6
Beds
3/1
Baths
4,300
Sqft
54 Wedgemere Avenue
Winchester, MA 01890
Year Built:
1915
HOA:
None
$11,000/mo
6
Beds
4/1
Baths
5,000
Sqft
52 North Border Rd. #52
Winchester, MA 01890
Year Built:
2008
HOA:
None
$10,000/mo
5
Beds
3/1
Baths
3,474
Sqft
211 Forest St
Winchester, MA 01890
Year Built:
--
HOA:
None
$8,500/mo
4
Beds
3/1
Baths
3,500
Sqft
35 Thornberry Road
Winchester, MA 01890
Year Built:
2010
HOA:
None
$8,000/mo
4
Beds
3
Baths
2,666
Sqft
10 Hillcrest Parkway
Winchester, MA 01890
Year Built:
1920
HOA:
None
$7,750/mo
4
Beds
3/1
Baths
3,500
Sqft
10 Farrow Street
Winchester, MA 01890
Year Built:
1955
HOA:
None
$7,500/mo
3
Beds
2/1
Baths
2,900
Sqft
846 Main Street #III
Winchester, MA 01890
Year Built:
2020
HOA:
None
$7,500/mo
3
Beds
2/1
Baths
2,900
Sqft
846 Main Street #IV
Winchester, MA 01890
Year Built:
2020
HOA:
None
$7,500/mo
3
Beds
3/1
Baths
3,218
Sqft
29 Wainwright Rd
Winchester, MA 01890
Year Built:
1978
HOA:
None
$7,000/mo
3
Beds
3
Baths
2,443
Sqft
25 Berkshire Dr
Winchester, MA 01890
Year Built:
1970
HOA:
None
$6,900/mo
4
Beds
4
Baths
3,639
Sqft
31 Coolidge Rd #31
Winchester, MA 01890
Year Built:
1980
HOA:
None
$6,000/mo
4
Beds
3/1
Baths
3,516
Sqft
192 Cross St #192
Winchester, MA 01890
Year Built:
2006
HOA:
None
$4,800/mo
3
Beds
2/1
Baths
2,339
Sqft
12 Trinity Road
Winchester, MA 01890
Year Built:
1963
HOA:
None
$4,400/mo
3
Beds
2/1
Baths
1,830
Sqft
171 Swanton St #65
Winchester, MA 01890
Year Built:
1985
HOA:
None
$4,200/mo
3
Beds
2/1
Baths
1,835
Sqft
171 Swanton St #79
Winchester, MA 01890
Year Built:
1985
HOA:
None
$3,900/mo
3
Beds
1/1
Bath
1,542
Sqft
104 Wendell Street
Winchester, MA 01890
Year Built:
1951
HOA:
None
$3,200/mo
2
Beds
1/1
Bath
1,464
Sqft
60 Lake St #I
Winchester, MA 01890
Year Built:
1976
HOA:
None
$3,200/mo
2
Beds
1/1
Bath
1,331
Sqft
29 Vine Street #3
Winchester, MA 01890
Year Built:
--
HOA:
None
$2,575/mo
2
Beds
2
Baths
900
Sqft
35 Vine Street #306
Winchester, MA 01890
Year Built:
--
HOA:
None
$2,500/mo
2
Beds
1
Bath
950
Sqft
343 Washington Street #343
Winchester, MA 01890
Year Built:
1926
HOA:
None
$2,450/mo
2
Beds
1
Bath
700
Sqft
6 Skillings #2
Winchester, MA 01890
Year Built:
--
HOA:
None
$2,200/mo
1
Bed
1
Bath
613
Sqft
200 Swanton St #713
Winchester, MA 01890
Year Built:
--
HOA:
None
$1,890/mo
1
Bed
1
Bath
380
Sqft
200 Swanton St #708
Winchester, MA 01890
Year Built:
--
HOA:
None
$1,800/mo
1
Bed
1
Bath
385
Sqft
200 Swanton #L6
Winchester, MA 01890
Year Built:
1966
HOA:
None
$1,780/mo
0
Beds
1
Bath
350
Sqft
200 Swanton #738
Winchester, MA 01890
Year Built:
--
HOA:
None
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