82 Homes for Sale in Winchester
$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
$3,295,000
6
Beds
6/1
Baths
6,100
Sqft
2 Atherton Rd
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
$3,200,000
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
$2,999,000
5
Beds
3/1
Baths
4,500
Sqft
5 Forest Cir
Winchester, MA 01890
Year Built:
2026
HOA:
None
$2,849,000
5
Beds
4/1
Baths
5,058
Sqft
7 Viking Rd
Winchester, MA 01890
Year Built:
1984
HOA:
None
$2,695,000
4
Beds
4/1
Baths
5,233
Sqft
18 Middlesex St
Winchester, MA 01890
Year Built:
2004
HOA:
None
$2,499,000
4
Beds
4/1
Baths
4,450
Sqft
54 Squire Road
Winchester, MA 01890
Year Built:
2016
HOA:
None
$2,400,000
5
Beds
3
Baths
4,071
Sqft
9 Plymouth Rd
Winchester, MA 01890
Year Built:
1959
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
4
Beds
3/1
Baths
3,640
Sqft
7 Wainwright Road #113
Winchester, MA 01890
Year Built:
1995
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
4
Beds
3/1
Baths
3,210
Sqft
26 N Gateway
Winchester, MA 01890
Year Built:
1959
HOA:
None
$1,999,000
4
Beds
2/1
Baths
3,757
Sqft
85 High St
Winchester, MA 01890
Year Built:
1931
HOA:
None
$1,899,000
5
Beds
3/1
Baths
3,210
Sqft
79 Grove St
Winchester, MA 01890
Year Built:
1941
HOA:
None
$1,749,000
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
$1,699,000
3
Beds
2
Baths
2,421
Sqft
4 Churchill Road
Winchester, MA 01890
Year Built:
1954
HOA:
None
$1,679,900
3
Beds
2
Baths
2,483
Sqft
5 Willowdale Rd
Winchester, MA 01890
Year Built:
1953
HOA:
None
$1,549,000
3
Beds
2/1
Baths
2,640
Sqft
50 Holland Street
Winchester, MA 01890
Year Built:
1960
HOA:
None
$1,350,000
4
Beds
3
Baths
2,690
Sqft
423 Washington St
Winchester, MA 01890
Year Built:
1850
HOA:
None
$1,329,000
3
Beds
2/1
Baths
2,459
Sqft
110 Thornberry Road
Winchester, MA 01890
Year Built:
1974
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
$1,099,000
4
Beds
2/1
Baths
2,411
Sqft
24 Richardson St
Winchester, MA 01890
Year Built:
2003
HOA:
None
$1,098,000
3
Beds
1/1
Bath
1,657
Sqft
17 Russell Rd
Winchester, MA 01890
Year Built:
1905
HOA:
None
$1,075,000
3
Beds
2/1
Baths
2,235
Sqft
53 Lake Street
Winchester, MA 01890
Year Built:
1864
HOA:
None
$1,050,000
5
Beds
2/1
Baths
2,801
Sqft
257 Cross Street
Winchester, MA 01890
Year Built:
1960
HOA:
None
$1,050,000
3
Beds
1/1
Bath
1,711
Sqft
150 Cambridge Street
Winchester, MA 01890
Year Built:
1940
HOA:
None
$999,900
4
Beds
2
Baths
1,719
Sqft
258 Cross Street
Winchester, MA 01890
Year Built:
1860
HOA:
None
$975,000
2
Beds
1/1
Bath
1,365
Sqft
83 Church Street #15
Winchester, MA 01890
Year Built:
1983
HOA:
None
$950,000
3
Beds
1/1
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
$849,000
3
Beds
1/1
Bath
1,340
Sqft
15 Clark St
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
$849,000
3
Beds
1/1
Bath
1,340
Sqft
15 Clark St #15
Winchester, MA 01890
Year Built:
1880
HOA:
None
$789,000
2
Beds
2
Baths
1,036
Sqft
50 Middlesex Street #50
Winchester, MA 01890
Year Built:
1920
HOA:
None
$685,000
2
Beds
2
Baths
1,170
Sqft
666 Main Street #211
Winchester, MA 01890
Year Built:
1982
HOA:
None
$675,000
2
Beds
1/1
Bath
1,190
Sqft
60 LakE St #E
Winchester, MA 01890
Year Built:
1976
HOA:
None
$650,000
3
Beds
2/1
Baths
1,494
Sqft
247 Washington St #11
Winchester, MA 01890
Year Built:
1975
HOA:
None
$649,900
2
Beds
2
Baths
1,025
Sqft
666 Main Street #315
Winchester, MA 01890
Year Built:
1982
HOA:
None
$619,000
3
Beds
2/2
Baths
1,225
Sqft
23 Shepard Ct #23
Winchester, MA 01890
Year Built:
1890
HOA:
None
$450,000
2
Beds
1
Bath
810
Sqft
200 Swanton Street #T35
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
$13,000/mo
6
Beds
5/1
Baths
6,400
Sqft
52 North Border Rd
Winchester, MA 01890
Year Built:
2008
HOA:
None
$11,500/mo
5
Beds
3
Baths
4,132
Sqft
10 Bellevue Avenue
Winchester, MA 01890
Year Built:
--
HOA:
None
$7,500/mo
6
Beds
1/2
Bath
3,000
Sqft
161 Highland Ave #n/a
Winchester, MA 01890
Year Built:
1880
HOA:
None
$6,500/mo
3
Beds
2/1
Baths
1,947
Sqft
60 Graystone Cir #60
Winchester, MA 01890
Year Built:
2011
HOA:
None
$6,000/mo
3
Beds
3
Baths
2,443
Sqft
25 Berkshire Dr
Winchester, MA 01890
Year Built:
1970
HOA:
None
$5,500/mo
3
Beds
2/1
Baths
2,632
Sqft
111 Highland Ave
Winchester, MA 01890
Year Built:
1940
HOA:
None
$5,000/mo
4
Beds
3/1
Baths
1,928
Sqft
48 Spruce St #1
Winchester, MA 01890
Year Built:
1940
HOA:
None
$5,000/mo
4
Beds
4
Baths
2,700
Sqft
270 Cross St #SF
Winchester, MA 01890
Year Built:
1955
HOA:
None
$4,950/mo
5
Beds
2
Baths
2,174
Sqft
79 Bacon St #79
Winchester, MA 01890
Year Built:
1910
HOA:
None
$4,800/mo
3
Beds
1/1
Bath
1,657
Sqft
17 Russell Rd
Winchester, MA 01890
Year Built:
--
HOA:
None
$4,400/mo
3
Beds
1/1
Bath
2,000
Sqft
79 Church St #1
Winchester, MA 01890
Year Built:
--
HOA:
None
$4,200/mo
3
Beds
2
Baths
1,678
Sqft
22 Baldwin St
Winchester, MA 01890
Year Built:
1875
HOA:
None
$4,200/mo
3
Beds
1/1
Bath
2,754
Sqft
16 Nathaniel Rd
Winchester, MA 01890
Year Built:
1950
HOA:
None
$4,100/mo
4
Beds
2
Baths
1,100
Sqft
7 Park Ave #7
Winchester, MA 01890
Year Built:
1915
HOA:
None
$3,895/mo
2
Beds
1
Bath
1,320
Sqft
77 Church Street #A
Winchester, MA 01890
Year Built:
--
HOA:
None
$3,700/mo
4
Beds
2
Baths
1,967
Sqft
10-12 Webster St #1
Winchester, MA 01890
Year Built:
1952
HOA:
None
$3,500/mo
3
Beds
1
Bath
1,700
Sqft
303 Washington Street #1
Winchester, MA 01890
Year Built:
--
HOA:
None
$3,500/mo
3
Beds
2
Baths
1,620
Sqft
28 East St #28
Winchester, MA 01890
Year Built:
1961
HOA:
None
$3,500/mo
2
Beds
1
Bath
1,000
Sqft
63 Holland St #63
Winchester, MA 01890
Year Built:
--
HOA:
None
$3,200/mo
2
Beds
2
Baths
1,025
Sqft
666 Main St #208
Winchester, MA 01890
Year Built:
--
HOA:
None
$3,200/mo
3
Beds
1/1
Bath
0
Sqft
5 Quigley Court #5
Winchester, MA 01890
Year Built:
--
HOA:
None
$3,200/mo
2
Beds
2
Baths
1,025
Sqft
666 Main Street #315-3
Winchester, MA 01890
Year Built:
1982
HOA:
None
$3,200/mo
2
Beds
1/1
Bath
1,460
Sqft
60 Lake St #D
Winchester, MA 01890
Year Built:
--
HOA:
None
$3,200/mo
2
Beds
1/1
Bath
1,200
Sqft
7 Ridge Street
Winchester, MA 01890
Year Built:
1975
HOA:
None
$3,000/mo
2
Beds
1
Bath
810
Sqft
200 Swanton Street #T35
Winchester, MA 01890
Year Built:
1966
HOA:
None
$3,000/mo
3
Beds
1
Bath
1,000
Sqft
341 Washington St #2
Winchester, MA 01890
Year Built:
1926
HOA:
None
$2,900/mo
3
Beds
2
Baths
1,200
Sqft
63-65 Harvard Street #2
Winchester, MA 01890
Year Built:
1880
HOA:
None
$2,800/mo
2
Beds
1
Bath
833
Sqft
200 Swanton St #705
Winchester, MA 01890
Year Built:
1966
HOA:
None
$2,700/mo
1
Bed
1
Bath
842
Sqft
115 Washington St #1B
Winchester, MA 01890
Year Built:
--
HOA:
None
$2,600/mo
2
Beds
1/1
Bath
1,120
Sqft
16 Lochwan Street #16
Winchester, MA 01890
Year Built:
1910
HOA:
None
$2,500/mo
2
Beds
1
Bath
1,100
Sqft
24 Lebanon St #1
Winchester, MA 01890
Year Built:
1928
HOA:
None
$1,950/mo
1
Bed
1
Bath
606
Sqft
200 Swanton Street #416
Winchester, MA 01890
Year Built:
1995
HOA:
None
$1,880/mo
0
Beds
1
Bath
350
Sqft
200 Swanton St #738
Winchester, MA 01890
Year Built:
--
HOA:
None
$1,800/mo
0
Beds
1
Bath
515
Sqft
200 Swanton St #T30
Winchester, MA 01890
Year Built:
1966
HOA:
None
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