66 Homes for Sale in Winchester
$18,000,000
6
Beds
6/1
Baths
10,000
Sqft
15 Vinson Circle
Winchester, MA 01890
Year Built:
2026
HOA:
None
$4,299,000
5
Beds
5/1
Baths
6,526
Sqft
4 Dartmouth St
Winchester, MA 01890
Year Built:
1935
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
$3,299,000
7
Beds
7/1
Baths
7,226
Sqft
1 Plymouth Rd
Winchester, MA 01890
Year Built:
2025
HOA:
None
$3,200,000
8
Beds
6/1
Baths
5,750
Sqft
30 Willowdale Rd
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
$3,200,000
5
Beds
5/1
Baths
5,295
Sqft
18 Ridge St
Winchester, MA 01890
Year Built:
2026
HOA:
None
$3,149,000
7
Beds
7/1
Baths
8,540
Sqft
37 Mayflower Road
Winchester, MA 01890
Year Built:
2009
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
$2,600,000
6
Beds
2/2
Baths
3,534
Sqft
7 Lakeview Terrace
Winchester, MA 01890
Year Built:
1910
HOA:
None
$2,399,000
4
Beds
2/2
Baths
3,550
Sqft
63 Wedgemere Avenue
Winchester, MA 01890
Year Built:
1947
HOA:
None
$2,399,000
4
Beds
4/1
Baths
4,450
Sqft
54 Squire Road
Winchester, MA 01890
Year Built:
2016
HOA:
None
$2,250,000
5
Beds
3
Baths
4,071
Sqft
9 Plymouth Rd
Winchester, MA 01890
Year Built:
1959
HOA:
None
$2,199,000
6
Beds
3/2
Baths
4,947
Sqft
42 Everett Ave
Winchester, MA 01890
Year Built:
1910
HOA:
None
$2,199,000
4
Beds
3/1
Baths
3,570
Sqft
19 Hancock Street
Winchester, MA 01890
Year Built:
2026
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
6
Beds
3/2
Baths
3,403
Sqft
6 Ivy Circle
Winchester, MA 01890
Year Built:
1966
HOA:
None
$2,049,000
5
Beds
3/1
Baths
4,063
Sqft
21 Amberwood Dr
Winchester, MA 01890
Year Built:
1973
HOA:
None
$1,999,000
4
Beds
3/1
Baths
3,640
Sqft
7 Wainwright Road #113
Winchester, MA 01890
Year Built:
1995
HOA:
None
$1,899,000
4
Beds
2/1
Baths
3,757
Sqft
85 High St
Winchester, MA 01890
Year Built:
1931
HOA:
None
$1,850,000
4
Beds
2/1
Baths
3,604
Sqft
1 Overlook Way
Winchester, MA 01890
Year Built:
1941
HOA:
None
$1,749,000
3
Beds
3/1
Baths
3,010
Sqft
1 Town Way
Winchester, MA 01890
Year Built:
2026
HOA:
None
$1,749,000
5
Beds
3/1
Baths
3,508
Sqft
17 Churchill Rd
Winchester, MA 01890
Year Built:
1966
HOA:
None
$1,650,000
5
Beds
3/1
Baths
3,722
Sqft
117 Highland Ave
Winchester, MA 01890
Year Built:
1953
HOA:
None
$1,649,000
3
Beds
2
Baths
2,421
Sqft
4 Churchill Road
Winchester, MA 01890
Year Built:
1954
HOA:
None
$1,549,000
3
Beds
2/1
Baths
2,640
Sqft
50 Holland Street
Winchester, MA 01890
Year Built:
1960
HOA:
None
$1,529,000
4
Beds
3/1
Baths
2,709
Sqft
25 Arlington St
Winchester, MA 01890
Year Built:
1953
HOA:
None
$1,495,000
4
Beds
2/1
Baths
2,973
Sqft
7 Sherman Place #7
Winchester, MA 01890
Year Built:
2005
HOA:
None
$1,399,000
5
Beds
1/1
Bath
2,071
Sqft
15 Lloyd Street
Winchester, MA 01890
Year Built:
1900
HOA:
None
$1,350,000
4
Beds
3
Baths
2,690
Sqft
423 Washington St
Winchester, MA 01890
Year Built:
1850
HOA:
None
$1,325,000
4
Beds
2
Baths
1,922
Sqft
9 Priscilla Ln
Winchester, MA 01890
Year Built:
1942
HOA:
None
$1,300,000
4
Beds
2/1
Baths
2,666
Sqft
465 Washington Street #465
Winchester, MA 01890
Year Built:
2017
HOA:
None
$1,300,000
4
Beds
2/1
Baths
2,666
Sqft
465 Washington Street
Winchester, MA 01890
Year Built:
2017
HOA:
None
$1,299,000
3
Beds
2
Baths
2,350
Sqft
39 Forest St
Winchester, MA 01890
Year Built:
1900
HOA:
None
$1,289,000
3
Beds
2/1
Baths
2,459
Sqft
110 Thornberry Road
Winchester, MA 01890
Year Built:
1974
HOA:
None
$1,195,000
3
Beds
1/1
Bath
2,239
Sqft
4 Stone Ave
Winchester, MA 01890
Year Built:
1920
HOA:
None
$1,098,000
3
Beds
1/1
Bath
1,657
Sqft
17 Russell Rd
Winchester, MA 01890
Year Built:
1905
HOA:
None
$1,080,000
3
Beds
1
Bath
1,382
Sqft
6 Reservoir Street
Winchester, MA 01890
Year Built:
1900
HOA:
None
$1,069,000
4
Beds
2/1
Baths
2,411
Sqft
24 Richardson St
Winchester, MA 01890
Year Built:
2003
HOA:
None
$1,050,000
5
Beds
2/1
Baths
2,801
Sqft
257 Cross Street
Winchester, MA 01890
Year Built:
1960
HOA:
None
$1,025,000
3
Beds
2/1
Baths
2,235
Sqft
53 Lake Street
Winchester, MA 01890
Year Built:
1864
HOA:
None
$974,900
3
Beds
2/1
Baths
1,719
Sqft
258 Cross St
Winchester, MA 01890
Year Built:
1860
HOA:
None
$950,000
2
Beds
1/1
Bath
1,365
Sqft
83 Church Street #15
Winchester, MA 01890
Year Built:
1983
HOA:
None
$919,999
4
Beds
2
Baths
2,326
Sqft
96 Loring Ave
Winchester, MA 01890
Year Built:
1951
HOA:
None
$899,000
3
Beds
1
Bath
1,313
Sqft
39 Henry Street
Winchester, MA 01890
Year Built:
1955
HOA:
None
$899,000
3
Beds
1/1
Bath
1,356
Sqft
47 Water Street
Winchester, MA 01890
Year Built:
1940
HOA:
None
$799,000
3
Beds
1/1
Bath
1,340
Sqft
15 Clark St
Winchester, MA 01890
Year Built:
1880
HOA:
None
$799,000
3
Beds
1/1
Bath
1,340
Sqft
15 Clark St #15
Winchester, MA 01890
Year Built:
1880
HOA:
None
$774,900
2
Beds
2
Baths
1,036
Sqft
50 Middlesex Street #50
Winchester, MA 01890
Year Built:
1920
HOA:
None
$769,000
2
Beds
2
Baths
1,170
Sqft
666 Main St #310
Winchester, MA 01890
Year Built:
1982
HOA:
None
$765,000
3
Beds
2
Baths
1,643
Sqft
189 Washington St #2
Winchester, MA 01890
Year Built:
1860
HOA:
None
$700,000
2
Beds
2
Baths
1,240
Sqft
666 Main Street #217
Winchester, MA 01890
Year Built:
1982
HOA:
None
$685,000
2
Beds
2
Baths
1,170
Sqft
666 Main Street #211
Winchester, MA 01890
Year Built:
1982
HOA:
None
$660,000
2
Beds
1/1
Bath
1,190
Sqft
60 LakE St #E
Winchester, MA 01890
Year Built:
1976
HOA:
None
$649,900
2
Beds
2
Baths
1,025
Sqft
666 Main Street #315
Winchester, MA 01890
Year Built:
1982
HOA:
None
$610,000
3
Beds
2/1
Baths
1,494
Sqft
247 Washington St #11
Winchester, MA 01890
Year Built:
1975
HOA:
None
$495,000
2
Beds
1
Bath
822
Sqft
200 Swanton St #303
Winchester, MA 01890
Year Built:
1966
HOA:
None
$450,000
2
Beds
1
Bath
810
Sqft
200 Swanton Street #T35
Winchester, MA 01890
Year Built:
1966
HOA:
None
$399,000
1
Bed
1
Bath
613
Sqft
200 Swanton St #727
Winchester, MA 01890
Year Built:
1966
HOA:
None
$359,900
2
Beds
1
Bath
1,084
Sqft
20 Arthur St #20
Winchester, MA 01890
Year Built:
1897
HOA:
None
$349,900
1
Bed
1
Bath
613
Sqft
200 Swanton St #717
Winchester, MA 01890
Year Built:
1966
HOA:
None
$329,900
2
Beds
1
Bath
1,084
Sqft
20 Arthur St #20
Winchester, MA 01890
Year Built:
1897
HOA:
None
$319,000
1
Bed
1
Bath
602
Sqft
200 Swanton St #T14
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
Showing 1 - 66 of 66 Results
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