104 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
$3,799,000
8
Beds
4/2
Baths
7,081
Sqft
15 Foxcroft Rd
Winchester, MA 01890
Year Built:
1880
HOA:
None
$3,600,000
7
Beds
7/1
Baths
7,429
Sqft
11 Viking Road
Winchester, MA 01890
Year Built:
2026
HOA:
None
$3,299,000
7
Beds
7/1
Baths
7,226
Sqft
1 Plymouth Rd
Winchester, MA 01890
Year Built:
2025
HOA:
None
$3,295,000
6
Beds
4/1
Baths
5,735
Sqft
7 Hutchinson Road
Winchester, MA 01890
Year Built:
2026
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
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
$2,999,000
5
Beds
4/1
Baths
4,900
Sqft
5 Forest Cir
Winchester, MA 01890
Year Built:
2026
HOA:
None
$2,995,000
6
Beds
5/1
Baths
6,100
Sqft
9 Albamont Road
Winchester, MA 01890
Year Built:
2026
HOA:
None
$2,950,000
6
Beds
4
Baths
4,752
Sqft
18 Surrey Road
Winchester, MA 01890
Year Built:
1983
HOA:
None
$2,750,000
6
Beds
5/2
Baths
6,968
Sqft
14 Nassau Drive
Winchester, MA 01890
Year Built:
2002
HOA:
None
$2,650,000
4
Beds
4/1
Baths
5,233
Sqft
18 Middlesex St
Winchester, MA 01890
Year Built:
2004
HOA:
None
$2,650,000
4
Beds
4/1
Baths
5,233
Sqft
18 Middlesex St
Winchester, MA 01890
Year Built:
2004
HOA:
None
$2,400,000
6
Beds
2/2
Baths
3,534
Sqft
7 Lakeview Terrace
Winchester, MA 01890
Year Built:
1910
HOA:
None
$2,299,000
4
Beds
4/1
Baths
4,450
Sqft
54 Squire Road
Winchester, MA 01890
Year Built:
2016
HOA:
None
$2,195,000
5
Beds
3/1
Baths
5,006
Sqft
276 High Street
Winchester, MA 01890
Year Built:
1992
HOA:
None
$2,175,000
5
Beds
3
Baths
4,071
Sqft
9 Plymouth Rd
Winchester, MA 01890
Year Built:
1959
HOA:
None
$2,149,000
4
Beds
3/1
Baths
3,570
Sqft
19 Hancock Street
Winchester, MA 01890
Year Built:
2026
HOA:
None
$2,100,000
6
Beds
3/2
Baths
3,403
Sqft
6 Ivy Circle
Winchester, MA 01890
Year Built:
1966
HOA:
None
$1,999,000
5
Beds
3/1
Baths
4,063
Sqft
21 Amberwood Dr
Winchester, MA 01890
Year Built:
1973
HOA:
None
$1,899,000
4
Beds
2/1
Baths
3,757
Sqft
85 High St
Winchester, MA 01890
Year Built:
1931
HOA:
None
$1,749,000
5
Beds
3/1
Baths
3,508
Sqft
17 Churchill Rd
Winchester, MA 01890
Year Built:
1966
HOA:
None
$1,749,000
4
Beds
2/1
Baths
3,757
Sqft
85 High Street
Winchester, MA 01890
Year Built:
1931
HOA:
None
$1,744,000
3
Beds
3/1
Baths
3,010
Sqft
1 Town Way
Winchester, MA 01890
Year Built:
2026
HOA:
None
$1,650,000
4
Beds
2/1
Baths
3,604
Sqft
1 Overlook Way
Winchester, MA 01890
Year Built:
1941
HOA:
None
$1,650,000
5
Beds
3/1
Baths
3,722
Sqft
117 Highland Ave
Winchester, MA 01890
Year Built:
1953
HOA:
None
$1,599,000
3
Beds
2/1
Baths
1,920
Sqft
9 Watson Pl
Winchester, MA 01890
Year Built:
2027
HOA:
None
$1,549,000
3
Beds
2/1
Baths
2,640
Sqft
50 Holland Street
Winchester, MA 01890
Year Built:
1960
HOA:
None
$1,495,000
4
Beds
2/1
Baths
2,973
Sqft
7 Sherman Place #7
Winchester, MA 01890
Year Built:
2005
HOA:
None
$1,449,000
4
Beds
2/1
Baths
2,855
Sqft
15 Madison Ave W Ave
Winchester, MA 01890
Year Built:
1924
HOA:
None
$1,399,000
3
Beds
2/1
Baths
1,975
Sqft
6 Aricia Ln
Winchester, MA 01890
Year Built:
1976
HOA:
None
$1,350,000
4
Beds
3
Baths
2,690
Sqft
423 Washington St
Winchester, MA 01890
Year Built:
1850
HOA:
None
$1,350,000
2
Beds
2/1
Baths
1,573
Sqft
36 Elmwood Ave #11
Winchester, MA 01890
Year Built:
2020
HOA:
None
$1,325,000
4
Beds
2
Baths
1,922
Sqft
9 Priscilla Ln
Winchester, MA 01890
Year Built:
1942
HOA:
None
$1,250,000
4
Beds
2/1
Baths
2,666
Sqft
465 Washington Street
Winchester, MA 01890
Year Built:
2017
HOA:
None
$1,250,000
4
Beds
2/1
Baths
2,666
Sqft
465 Washington Street #465
Winchester, MA 01890
Year Built:
2017
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
$1,050,000
5
Beds
2/1
Baths
2,801
Sqft
257 Cross Street
Winchester, MA 01890
Year Built:
1960
HOA:
None
$1,049,900
3
Beds
2
Baths
1,783
Sqft
28 Olive St
Winchester, MA 01890
Year Built:
1963
HOA:
None
$1,049,000
4
Beds
2/1
Baths
2,411
Sqft
24 Richardson St
Winchester, MA 01890
Year Built:
2003
HOA:
None
$999,000
3
Beds
2/1
Baths
2,235
Sqft
53 Lake Street
Winchester, MA 01890
Year Built:
1864
HOA:
None
$919,999
4
Beds
2
Baths
2,326
Sqft
96 Loring Ave
Winchester, MA 01890
Year Built:
1951
HOA:
None
$919,000
4
Beds
2/1
Baths
1,719
Sqft
258 Cross St
Winchester, MA 01890
Year Built:
1860
HOA:
None
$850,000
3
Beds
1
Bath
1,313
Sqft
39 Henry Street
Winchester, MA 01890
Year Built:
1955
HOA:
None
$815,000
2
Beds
1
Bath
1,489
Sqft
80 Nelson St
Winchester, MA 01890
Year Built:
1880
HOA:
None
$799,000
3
Beds
1/1
Bath
1,340
Sqft
15 Clark St
Winchester, MA 01890
Year Built:
1880
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
$749,000
2
Beds
2
Baths
1,036
Sqft
50 Middlesex Street #50
Winchester, MA 01890
Year Built:
1920
HOA:
None
$700,000
2
Beds
2
Baths
1,240
Sqft
666 Main Street #217
Winchester, MA 01890
Year Built:
1982
HOA:
None
$675,000
3
Beds
1
Bath
1,524
Sqft
419 Washington Street #419
Winchester, MA 01890
Year Built:
1910
HOA:
None
$664,000
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
$649,000
3
Beds
1
Bath
1,422
Sqft
421 Washington Street #421
Winchester, MA 01890
Year Built:
1910
HOA:
None
$600,000
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
$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
$288,750
1
Bed
1
Bath
388
Sqft
200 Swanton St #L8
Winchester, MA 01890
Year Built:
1964
HOA:
None
$11,500/mo
5
Beds
3
Baths
4,132
Sqft
10 Bellevue Avenue
Winchester, MA 01890
Year Built:
--
HOA:
None
$8,000/mo
4
Beds
4/1
Baths
3,881
Sqft
14a Hillside Ave
Winchester, MA 01890
Year Built:
1870
HOA:
None
$7,500/mo
6
Beds
2/2
Baths
3,000
Sqft
161 Highland Ave #n/a
Winchester, MA 01890
Year Built:
1880
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
$4,850/mo
5
Beds
2
Baths
2,174
Sqft
79 Bacon St #79
Winchester, MA 01890
Year Built:
1910
HOA:
None
$4,500/mo
3
Beds
3/1
Baths
1,520
Sqft
5A Euclid Ave #5A
Winchester, MA 01890
Year Built:
1896
HOA:
None
$4,500/mo
4
Beds
2/1
Baths
1,719
Sqft
258 Cross Street
Winchester, MA 01890
Year Built:
1860
HOA:
None
$4,200/mo
3
Beds
1/1
Bath
2,000
Sqft
79 Church Street #1-1
Winchester, MA 01890
Year Built:
--
HOA:
None
$4,200/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
2/1
Baths
1,835
Sqft
171 Swanton St #79
Winchester, MA 01890
Year Built:
1985
HOA:
None
$4,000/mo
3
Beds
1/1
Bath
1,657
Sqft
17 Russell Rd
Winchester, MA 01890
Year Built:
--
HOA:
None
$3,950/mo
3
Beds
1/1
Bath
2,754
Sqft
16 Nathaniel Rd
Winchester, MA 01890
Year Built:
1950
HOA:
None
$3,900/mo
2
Beds
2
Baths
1,170
Sqft
666 Main St #310
Winchester, MA 01890
Year Built:
1982
HOA:
None
$3,900/mo
3
Beds
1/1
Bath
2,030
Sqft
2 Wyman Ct #1
Winchester, MA 01890
Year Built:
1912
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
$3,650/mo
3
Beds
2/1
Baths
1,367
Sqft
52 Sheridan Circle #52
Winchester, MA 01890
Year Built:
1997
HOA:
None
$3,600/mo
3
Beds
2
Baths
1,600
Sqft
38-40 Florence Street #2
Winchester, MA 01890
Year Built:
1915
HOA:
None
$3,500/mo
2
Beds
2
Baths
1,150
Sqft
7 Conant Rd #19
Winchester, MA 01890
Year Built:
--
HOA:
None
$3,500/mo
3
Beds
1/1
Bath
968
Sqft
34 Charles Road #34
Winchester, MA 01890
Year Built:
1963
HOA:
None
$3,350/mo
3
Beds
2
Baths
1,620
Sqft
28 East St #28
Winchester, MA 01890
Year Built:
1961
HOA:
None
$3,250/mo
2
Beds
2/1
Baths
1,924
Sqft
60 Lake Street #J
Winchester, MA 01890
Year Built:
1976
HOA:
None
$3,200/mo
3
Beds
1/1
Bath
0
Sqft
5 Quigley Court #1
Winchester, MA 01890
Year Built:
--
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
3
Beds
1/1
Bath
0
Sqft
5 Quigley Court #5
Winchester, MA 01890
Year Built:
--
HOA:
None
$3,100/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
1,000
Sqft
63 Holland St #63
Winchester, MA 01890
Year Built:
--
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
2
Beds
2
Baths
1,025
Sqft
666 Main St #208
Winchester, MA 01890
Year Built:
--
HOA:
None
$2,750/mo
2
Beds
1
Bath
1,100
Sqft
238 Washington St #1
Winchester, MA 01890
Year Built:
--
HOA:
None
$2,700/mo
3
Beds
2
Baths
1,200
Sqft
63-65 Harvard Street #2
Winchester, MA 01890
Year Built:
1880
HOA:
None
$2,600/mo
2
Beds
1
Bath
793
Sqft
22 Salem St #1
Winchester, MA 01890
Year Built:
1890
HOA:
None
$2,500/mo
2
Beds
1
Bath
800
Sqft
200 Swanton St #635
Winchester, MA 01890
Year Built:
1966
HOA:
None
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