80 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
$3,350,000
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
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
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
$2,795,000
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
5
Beds
3/1
Baths
5,230
Sqft
78 Bacon Street
Winchester, MA 01890
Year Built:
1910
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
$2,295,000
5
Beds
3/1
Baths
4,591
Sqft
21 Willowdale Road
Winchester, MA 01890
Year Built:
2019
HOA:
None
$2,195,000
5
Beds
3/1
Baths
5,006
Sqft
276 High Street
Winchester, MA 01890
Year Built:
1992
HOA:
None
$2,099,000
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
$1,899,000
6
Beds
4/1
Baths
6,900
Sqft
16 & 16a Glenwood Ave
Winchester, MA 01890
Year Built:
1966
HOA:
None
$1,799,000
3
Beds
3/1
Baths
3,010
Sqft
1 Town Way
Winchester, MA 01890
Year Built:
2026
HOA:
None
$1,725,000
5
Beds
3/1
Baths
3,722
Sqft
117 Highland Ave
Winchester, MA 01890
Year Built:
1953
HOA:
None
$1,699,000
3
Beds
3/1
Baths
2,513
Sqft
2 Olde Lyme Road
Winchester, MA 01890
Year Built:
1960
HOA:
None
$1,599,000
4
Beds
2/2
Baths
2,480
Sqft
241 Ridge St
Winchester, MA 01890
Year Built:
2001
HOA:
None
$1,350,000
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
$1,199,000
3
Beds
2/1
Baths
2,235
Sqft
53 Lake Street
Winchester, MA 01890
Year Built:
1864
HOA:
None
$1,175,000
3
Beds
1/2
Bath
1,736
Sqft
38 Robinhood Rd
Winchester, MA 01890
Year Built:
1956
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
2,004
Sqft
52 Salem Street #52
Winchester, MA 01890
Year Built:
1880
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
$1,100,000
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
$1,099,000
4
Beds
1/1
Bath
1,777
Sqft
46 Clark St
Winchester, MA 01890
Year Built:
1921
HOA:
None
$1,099,000
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
$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
$929,900
4
Beds
2
Baths
1,938
Sqft
380 Cross Street
Winchester, MA 01890
Year Built:
1939
HOA:
None
$888,000
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
$729,000
3
Beds
2/1
Baths
1,494
Sqft
247 Washington St #11
Winchester, MA 01890
Year Built:
1975
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
$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
$364,900
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
$15,000/mo
6
Beds
7
Baths
8,866
Sqft
20 Amberwood Dr
Winchester, MA 01890
Year Built:
2024
HOA:
None
$15,000/mo
5
Beds
4/1
Baths
5,820
Sqft
186 Ridge Street
Winchester, MA 01890
Year Built:
2020
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
$12,000/mo
4
Beds
3/1
Baths
4,300
Sqft
59 Wedgemere Avenue
Winchester, MA 01890
Year Built:
1931
HOA:
None
$6,995/mo
4
Beds
2/1
Baths
4,253
Sqft
18 Grant Road
Winchester, MA 01890
Year Built:
2021
HOA:
None
$6,500/mo
4
Beds
2/1
Baths
2,800
Sqft
46 Loring Avenue
Winchester, MA 01890
Year Built:
2008
HOA:
None
$6,000/mo
3
Beds
2
Baths
3,500
Sqft
31 Fells Road
Winchester, MA 01890
Year Built:
--
HOA:
None
$5,750/mo
5
Beds
3/1
Baths
3,404
Sqft
17 Churchill Road
Winchester, MA 01890
Year Built:
1966
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
3
Beds
3/1
Baths
2,420
Sqft
129 Washington St #129
Winchester, MA 01890
Year Built:
--
HOA:
None
$4,800/mo
3
Beds
1/1
Bath
1,657
Sqft
17 Russell Rd
Winchester, MA 01890
Year Built:
--
HOA:
None
$4,700/mo
3
Beds
2
Baths
1,678
Sqft
22 Baldwin St
Winchester, MA 01890
Year Built:
1875
HOA:
None
$4,650/mo
4
Beds
1/1
Bath
1,700
Sqft
488 Washington Street
Winchester, MA 01890
Year Built:
1927
HOA:
None
$4,600/mo
3
Beds
1/1
Bath
2,754
Sqft
16 Nathaniel Rd
Winchester, MA 01890
Year Built:
1950
HOA:
None
$4,550/mo
3
Beds
2/1
Baths
1,826
Sqft
171 Swanton St #77
Winchester, MA 01890
Year Built:
--
HOA:
None
$3,900/mo
4
Beds
2
Baths
1,967
Sqft
10-12 Webster St #1
Winchester, MA 01890
Year Built:
--
HOA:
None
$3,800/mo
2
Beds
1/1
Bath
1,500
Sqft
33 Nelson St
Winchester, MA 01890
Year Built:
1898
HOA:
None
$3,600/mo
3
Beds
2
Baths
2,400
Sqft
16-18 Richardson St #16
Winchester, MA 01890
Year Built:
1930
HOA:
None
$3,500/mo
2
Beds
1
Bath
1,000
Sqft
63 Holland St #63
Winchester, MA 01890
Year Built:
--
HOA:
None
$3,300/mo
3
Beds
2
Baths
1,200
Sqft
63-65 Harvard Street #2
Winchester, MA 01890
Year Built:
1880
HOA:
None
$3,200/mo
2
Beds
1/1
Bath
1,460
Sqft
60 Lake St #D
Winchester, MA 01890
Year Built:
--
HOA:
None
$2,800/mo
2
Beds
1
Bath
810
Sqft
200 Swanton Street #T35
Winchester, MA 01890
Year Built:
1966
HOA:
None
$2,675/mo
2
Beds
1
Bath
850
Sqft
200 Swanton St #T37
Winchester, MA 01890
Year Built:
1966
HOA:
None
$2,495/mo
2
Beds
1
Bath
833
Sqft
200 Swanton Street #507
Winchester, MA 01890
Year Built:
--
HOA:
None
$2,250/mo
1
Bed
1
Bath
606
Sqft
200 Swanton St #318
Winchester, MA 01890
Year Built:
1966
HOA:
None
$2,250/mo
1
Bed
1
Bath
606
Sqft
200 Swanton St #222
Winchester, MA 01890
Year Built:
1966
HOA:
None
$2,150/mo
1
Bed
1
Bath
606
Sqft
200 Swanton St #412
Winchester, MA 01890
Year Built:
1966
HOA:
None
$1,950/mo
1
Bed
1
Bath
606
Sqft
200 Swanton Street #416
Winchester, MA 01890
Year Built:
1995
HOA:
None
$1,800/mo
1
Bed
1
Bath
450
Sqft
200 Swanton St #T34
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
Showing 1 - 80 of 80 Results
Listing Saved!
Get alerts on new listings and listing updates that match below search criteria
Add to Collection
Organize and manage your saved listings by addint it to a collection
