60 Homes for Sale in Winchester
$3,600,000
6
Beds
7
Baths
8,866
Sqft
20 Amberwood Dr
Winchester, MA 01890
Year Built:
2024
HOA:
None
$3,600,000
7
Beds
7/1
Baths
7,429
Sqft
11 Viking Road
Winchester, MA 01890
Year Built:
2026
HOA:
None
$3,450,000
6
Beds
4/1
Baths
5,735
Sqft
7 Hutchinson Road
Winchester, MA 01890
Year Built:
2026
HOA:
None
$3,350,000
6
Beds
6/1
Baths
7,400
Sqft
2 Atherton Rd
Winchester, MA 01890
Year Built:
2025
HOA:
None
$3,299,000
7
Beds
7/1
Baths
7,226
Sqft
1 Plymouth Rd
Winchester, MA 01890
Year Built:
2025
HOA:
None
$3,200,000
5
Beds
5/1
Baths
5,295
Sqft
18 Ridge St
Winchester, MA 01890
Year Built:
2026
HOA:
None
$3,200,000
6
Beds
5/1
Baths
6,100
Sqft
9 Albamont Road
Winchester, MA 01890
Year Built:
2026
HOA:
None
$3,199,000
5
Beds
4/1
Baths
5,406
Sqft
10 Rangeley Road
Winchester, MA 01890
Year Built:
1911
HOA:
None
$3,179,000
7
Beds
7/1
Baths
8,540
Sqft
37 Mayflower Road
Winchester, MA 01890
Year Built:
2009
HOA:
None
$3,149,000
5
Beds
5/1
Baths
6,500
Sqft
8 Priscilla Ln
Winchester, MA 01890
Year Built:
2025
HOA:
None
$2,999,000
4
Beds
3/1
Baths
4,500
Sqft
5 Forest Cir
Winchester, MA 01890
Year Built:
2026
HOA:
None
$2,999,000
5
Beds
2/2
Baths
4,028
Sqft
10 Dartmouth Street
Winchester, MA 01890
Year Built:
1964
HOA:
None
$2,799,000
6
Beds
5/2
Baths
6,968
Sqft
14 Nassau Drive
Winchester, MA 01890
Year Built:
2002
HOA:
None
$2,695,000
4
Beds
4/1
Baths
5,233
Sqft
18 Middlesex St
Winchester, MA 01890
Year Built:
2004
HOA:
None
$2,500,000
5
Beds
3
Baths
4,071
Sqft
9 Plymouth Rd
Winchester, MA 01890
Year Built:
1959
HOA:
None
$2,499,000
4
Beds
4/1
Baths
4,450
Sqft
54 Squire Road
Winchester, MA 01890
Year Built:
2016
HOA:
None
$2,399,000
5
Beds
4
Baths
5,083
Sqft
53 Winford Way
Winchester, MA 01890
Year Built:
2025
HOA:
None
$2,300,000
4
Beds
4/1
Baths
3,881
Sqft
14 Hillside Ave
Winchester, MA 01890
Year Built:
1870
HOA:
None
$2,195,000
5
Beds
3/1
Baths
5,006
Sqft
276 High Street
Winchester, MA 01890
Year Built:
1992
HOA:
None
$2,100,000
4
Beds
3/1
Baths
3,640
Sqft
7 Wainwright Road #113
Winchester, MA 01890
Year Built:
1995
HOA:
None
$2,099,000
4
Beds
3/1
Baths
3,210
Sqft
26 N Gateway
Winchester, MA 01890
Year Built:
1959
HOA:
None
$1,925,000
4
Beds
3/1
Baths
3,286
Sqft
15 Fieldstone Dr
Winchester, MA 01890
Year Built:
1989
HOA:
None
$1,899,000
4
Beds
2/1
Baths
3,091
Sqft
9 Brookside Place
Winchester, MA 01890
Year Built:
1920
HOA:
None
$1,899,000
5
Beds
3/1
Baths
3,210
Sqft
79 Grove St
Winchester, MA 01890
Year Built:
1941
HOA:
None
$1,799,000
3
Beds
3/1
Baths
3,010
Sqft
1 Town Way
Winchester, MA 01890
Year Built:
2026
HOA:
None
$1,794,000
3
Beds
3/1
Baths
3,010
Sqft
1 Town Way
Winchester, MA 01890
Year Built:
2026
HOA:
None
$1,675,000
5
Beds
3/1
Baths
3,722
Sqft
117 Highland Ave
Winchester, MA 01890
Year Built:
1953
HOA:
None
$1,599,000
4
Beds
2/2
Baths
2,480
Sqft
241 Ridge St
Winchester, MA 01890
Year Built:
2001
HOA:
None
$1,599,000
4
Beds
2/2
Baths
2,480
Sqft
241 Ridge St
Winchester, MA 01890
Year Built:
2001
HOA:
None
$1,549,000
3
Beds
2/1
Baths
2,640
Sqft
50 Holland Street
Winchester, MA 01890
Year Built:
1960
HOA:
None
$1,499,995
3
Beds
2/1
Baths
2,459
Sqft
110 Thornberry Road
Winchester, MA 01890
Year Built:
1974
HOA:
None
$1,350,000
4
Beds
3
Baths
2,690
Sqft
423 Washington St
Winchester, MA 01890
Year Built:
1850
HOA:
None
$1,299,000
3
Beds
3
Baths
2,145
Sqft
7 Wainwright Road #47
Winchester, MA 01890
Year Built:
1987
HOA:
None
$1,150,000
3
Beds
2/1
Baths
2,004
Sqft
52 Salem Street #52
Winchester, MA 01890
Year Built:
1880
HOA:
None
$1,150,000
3
Beds
2/1
Baths
2,235
Sqft
53 Lake Street
Winchester, MA 01890
Year Built:
1864
HOA:
None
$1,149,000
5
Beds
2/1
Baths
2,578
Sqft
7-9 Cleveland Rd
Winchester, MA 01890
Year Built:
1976
HOA:
None
$1,125,000
3
Beds
1/2
Bath
1,736
Sqft
38 Robinhood Rd
Winchester, MA 01890
Year Built:
1956
HOA:
None
$1,100,000
4
Beds
2
Baths
2,085
Sqft
41 Cross St
Winchester, MA 01890
Year Built:
1860
HOA:
None
$1,099,000
3
Beds
3/1
Baths
2,420
Sqft
129 Washington St #129
Winchester, MA 01890
Year Built:
1890
HOA:
None
$1,064,000
4
Beds
1/1
Bath
1,777
Sqft
46 Clark St
Winchester, MA 01890
Year Built:
1921
HOA:
None
$999,900
4
Beds
2
Baths
1,719
Sqft
258 Cross Street
Winchester, MA 01890
Year Built:
1860
HOA:
None
$999,000
2
Beds
1/1
Bath
1,365
Sqft
83 Church Street #15
Winchester, MA 01890
Year Built:
1983
HOA:
None
$950,000
3
Beds
1
Bath
1,356
Sqft
47 Water Street
Winchester, MA 01890
Year Built:
1940
HOA:
None
$949,999
4
Beds
2
Baths
2,326
Sqft
96 Loring Ave
Winchester, MA 01890
Year Built:
1951
HOA:
None
$929,900
4
Beds
2
Baths
1,938
Sqft
380 Cross Street
Winchester, MA 01890
Year Built:
1939
HOA:
None
$849,000
3
Beds
1/1
Bath
1,340
Sqft
15 Clark St
Winchester, MA 01890
Year Built:
1880
HOA:
None
$849,000
3
Beds
1/1
Bath
1,340
Sqft
15 Clark St #15
Winchester, MA 01890
Year Built:
1880
HOA:
None
$849,000
4
Beds
2
Baths
2,083
Sqft
84 Oak Street
Winchester, MA 01890
Year Built:
1962
HOA:
None
$799,000
2
Beds
2
Baths
1,036
Sqft
50 Middlesex Street #50
Winchester, MA 01890
Year Built:
1920
HOA:
None
$719,000
3
Beds
2/1
Baths
1,494
Sqft
247 Washington St #11
Winchester, MA 01890
Year Built:
1975
HOA:
None
$700,000
2
Beds
2
Baths
1,170
Sqft
666 Main St #211
Winchester, MA 01890
Year Built:
1982
HOA:
None
$699,900
3
Beds
2/2
Baths
1,380
Sqft
23 Shepard Ct #U23
Winchester, MA 01890
Year Built:
1890
HOA:
None
$699,000
3
Beds
2/2
Baths
1,380
Sqft
23 Shepard Ct #U23
Winchester, MA 01890
Year Built:
1890
HOA:
None
$649,900
2
Beds
2
Baths
1,025
Sqft
666 Main Street #315
Winchester, MA 01890
Year Built:
1982
HOA:
None
$499,999
2
Beds
1
Bath
822
Sqft
200 Swanton St #303
Winchester, MA 01890
Year Built:
1966
HOA:
None
$400,000
2
Beds
1
Bath
810
Sqft
200 Swanton Street #T35
Winchester, MA 01890
Year Built:
1966
HOA:
None
$374,900
1
Bed
1
Bath
606
Sqft
200 Swanton St #412
Winchester, MA 01890
Year Built:
1966
HOA:
None
$349,900
1
Bed
1
Bath
613
Sqft
200 Swanton St #717
Winchester, MA 01890
Year Built:
1966
HOA:
None
$288,750
1
Bed
1
Bath
388
Sqft
200 Swanton St #L8
Winchester, MA 01890
Year Built:
1964
HOA:
None
$8,500
6
Beds
1/2
Bath
3,000
Sqft
161 Highland Ave
Winchester, MA 01890
Year Built:
1880
HOA:
None
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