68 Homes for Sale in Winchester
$4,100,000
7
Beds
5/3
Baths
7,587
Sqft
25 Wedgemere Ave
Winchester, MA 01890
Year Built:
2010
HOA:
None
$3,989,000
6
Beds
6/1
Baths
8,463
Sqft
26 Swan Road
Winchester, MA 01890
Year Built:
2006
HOA:
None
$3,799,900
7
Beds
7/1
Baths
7,429
Sqft
11 Viking Rd
Winchester, MA 01890
Year Built:
2025
HOA:
None
$3,699,000
7
Beds
7/1
Baths
7,982
Sqft
54 Johnson Road
Winchester, MA 01890
Year Built:
2024
HOA:
None
$3,698,000
6
Beds
7
Baths
8,866
Sqft
20 Amberwood Dr
Winchester, MA 01890
Year Built:
2024
HOA:
None
$3,599,000
6
Beds
5/1
Baths
7,431
Sqft
27 Everett Ave
Winchester, MA 01890
Year Built:
1905
HOA:
None
$3,199,000
6
Beds
3/1
Baths
5,238
Sqft
54 Wedgemere Avenue
Winchester, MA 01890
Year Built:
1915
HOA:
None
$3,199,000
6
Beds
3/2
Baths
5,198
Sqft
21 Sheffield West
Winchester, MA 01890
Year Built:
1910
HOA:
None
$3,149,000
7
Beds
5/1
Baths
6,200
Sqft
10 Sheffield Road
Winchester, MA 01890
Year Built:
1916
HOA:
None
$2,999,999
5
Beds
4/1
Baths
5,716
Sqft
Lot 3 Abby Road
Winchester, MA 01890
Year Built:
2025
HOA:
None
$2,999,000
5
Beds
4/2
Baths
5,354
Sqft
8 Chestnut St
Winchester, MA 01890
Year Built:
1850
HOA:
None
$2,950,000
6
Beds
5/2
Baths
6,968
Sqft
14 Nassau Drive
Winchester, MA 01890
Year Built:
2002
HOA:
None
$2,899,000
5
Beds
5/1
Baths
4,627
Sqft
11 Taft Dr
Winchester, MA 01890
Year Built:
2025
HOA:
None
$2,899,000
5
Beds
4/1
Baths
6,904
Sqft
11 Fieldstone Drive
Winchester, MA 01890
Year Built:
1989
HOA:
None
$2,850,000
4
Beds
3
Baths
4,276
Sqft
8 Tanglewood Lane
Winchester, MA 01890
Year Built:
1985
HOA:
None
$2,749,000
6
Beds
4/1
Baths
5,824
Sqft
107 Cambridge Street
Winchester, MA 01890
Year Built:
1911
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
4
Beds
2/2
Baths
4,704
Sqft
34 Swan Road
Winchester, MA 01890
Year Built:
1954
HOA:
None
$2,599,000
4
Beds
4/1
Baths
5,501
Sqft
15 Churchill Road
Winchester, MA 01890
Year Built:
2024
HOA:
None
$2,499,000
6
Beds
3/1
Baths
4,667
Sqft
9 Prospect St
Winchester, MA 01890
Year Built:
1895
HOA:
None
$2,450,000
5
Beds
5
Baths
3,940
Sqft
17 Wagon Wheel Rd
Winchester, MA 01890
Year Built:
1983
HOA:
None
$2,449,000
4
Beds
3/1
Baths
4,959
Sqft
5 Azalea Rd
Winchester, MA 01890
Year Built:
1980
HOA:
None
$2,399,000
5
Beds
3/1
Baths
5,077
Sqft
276 High Street
Winchester, MA 01890
Year Built:
1992
HOA:
None
$2,099,000
6
Beds
3/1
Baths
4,696
Sqft
5 Squire Rd
Winchester, MA 01890
Year Built:
2016
HOA:
None
$1,995,000
3
Beds
2
Baths
2,813
Sqft
20 Seneca Road
Winchester, MA 01890
Year Built:
1930
HOA:
None
$1,899,000
5
Beds
3/1
Baths
3,478
Sqft
10 Olde Lyme Road
Winchester, MA 01890
Year Built:
1960
HOA:
None
$1,599,000
6
Beds
2/1
Baths
3,543
Sqft
189 Mystic Valley Pkwy
Winchester, MA 01890
Year Built:
1850
HOA:
None
$1,599,000
3
Beds
2/1
Baths
2,605
Sqft
14 Hillside Ave
Winchester, MA 01890
Year Built:
1870
HOA:
None
$1,500,000
4
Beds
1/2
Bath
2,897
Sqft
195 Mystic Valley Parkway
Winchester, MA 01890
Year Built:
1934
HOA:
None
$1,499,900
5
Beds
2
Baths
3,033
Sqft
7 Thornberry Road
Winchester, MA 01890
Year Built:
1957
HOA:
None
$1,449,900
4
Beds
2/1
Baths
3,157
Sqft
63 Church Street #63
Winchester, MA 01890
Year Built:
1866
HOA:
None
$1,449,000
3
Beds
2/1
Baths
2,282
Sqft
20 Fletcher Street #20
Winchester, MA 01890
Year Built:
2025
HOA:
None
$1,449,000
3
Beds
2/1
Baths
2,282
Sqft
20 Fletcher Street #20
Winchester, MA 01890
Year Built:
2025
HOA:
None
$1,399,000
3
Beds
2
Baths
1,884
Sqft
147 Highland Ave
Winchester, MA 01890
Year Built:
1919
HOA:
None
$1,389,000
3
Beds
2/2
Baths
3,351
Sqft
34 Fells Road
Winchester, MA 01890
Year Built:
1946
HOA:
None
$1,295,000
4
Beds
1/1
Bath
2,202
Sqft
71 Woodside Rd
Winchester, MA 01890
Year Built:
1927
HOA:
None
$1,150,000
4
Beds
2
Baths
2,621
Sqft
61 Westland Avenue
Winchester, MA 01890
Year Built:
1952
HOA:
None
$749,900
2
Beds
2/1
Baths
1,539
Sqft
7 Conant Rd #37
Winchester, MA 01890
Year Built:
1999
HOA:
None
$734,900
2
Beds
2/1
Baths
1,634
Sqft
7 Conant Road #60
Winchester, MA 01890
Year Built:
1999
HOA:
None
$699,900
2
Beds
2
Baths
1,168
Sqft
7 Conant Rd #20
Winchester, MA 01890
Year Built:
2000
HOA:
None
$385,000
1
Bed
1
Bath
613
Sqft
200 Swanton St #722
Winchester, MA 01890
Year Built:
1966
HOA:
None
$299,000
1
Bed
1
Bath
450
Sqft
200 Swanton St #T4
Winchester, MA 01890
Year Built:
1966
HOA:
None
$11,000/mo
4
Beds
4
Baths
4,650
Sqft
31 Coolidge St
Winchester, MA 01890
Year Built:
1980
HOA:
None
$11,000/mo
7
Beds
3/1
Baths
3,300
Sqft
34 Glen Road
Winchester, MA 01890
Year Built:
--
HOA:
None
$11,000/mo
6
Beds
4/1
Baths
6,500
Sqft
52 North Border Rd.
Winchester, MA 01890
Year Built:
2008
HOA:
None
$9,500/mo
6
Beds
4/1
Baths
3,118
Sqft
23 Jefferson Road
Winchester, MA 01890
Year Built:
1929
HOA:
None
$8,000/mo
5
Beds
3/1
Baths
3,700
Sqft
271 Washington #1
Winchester, MA 01890
Year Built:
--
HOA:
None
$8,000/mo
3
Beds
2/1
Baths
2,900
Sqft
846 Main Street #4
Winchester, MA 01890
Year Built:
2020
HOA:
None
$6,500/mo
4
Beds
3/1
Baths
4,000
Sqft
40 Church #A
Winchester, MA 01890
Year Built:
2016
HOA:
None
$5,500/mo
4
Beds
3/1
Baths
2,500
Sqft
48 Spruce #48
Winchester, MA 01890
Year Built:
--
HOA:
None
$5,000/mo
3
Beds
1/1
Bath
2,364
Sqft
27 Ledyard Road #SF
Winchester, MA 01890
Year Built:
1940
HOA:
None
$4,950/mo
5
Beds
2
Baths
2,095
Sqft
137 Ridge St
Winchester, MA 01890
Year Built:
--
HOA:
None
$4,500/mo
4
Beds
1/1
Bath
1,630
Sqft
488 Washington Street
Winchester, MA 01890
Year Built:
1927
HOA:
None
$4,500/mo
3
Beds
1/1
Bath
1,657
Sqft
17 Russell Rd
Winchester, MA 01890
Year Built:
1905
HOA:
None
$4,500/mo
3
Beds
2/1
Baths
1,823
Sqft
171 Swanton Street #63
Winchester, MA 01890
Year Built:
1985
HOA:
None
$4,300/mo
2
Beds
2/1
Baths
1,260
Sqft
83 Church #9
Winchester, MA 01890
Year Built:
--
HOA:
None
$4,300/mo
2
Beds
1
Bath
1,200
Sqft
67 Church #67
Winchester, MA 01890
Year Built:
--
HOA:
None
$4,000/mo
2
Beds
2/1
Baths
1,430
Sqft
171 Swaton St #16
Winchester, MA 01890
Year Built:
1984
HOA:
None
$3,850/mo
3
Beds
2
Baths
1,451
Sqft
50 Lake Street #F
Winchester, MA 01890
Year Built:
1976
HOA:
None
$3,600/mo
3
Beds
2
Baths
2,100
Sqft
38 Florence Street #38
Winchester, MA 01890
Year Built:
1915
HOA:
None
$3,300/mo
3
Beds
2
Baths
2,400
Sqft
16 Richardson #16
Winchester, MA 01890
Year Built:
1930
HOA:
None
$3,000/mo
3
Beds
1/1
Bath
1,452
Sqft
11 Bradford #11
Winchester, MA 01890
Year Built:
--
HOA:
None
$3,000/mo
2
Beds
1
Bath
1,200
Sqft
13 Oak Street #1
Winchester, MA 01890
Year Built:
1922
HOA:
None
$2,680/mo
2
Beds
1
Bath
606
Sqft
200 Swanton St #239
Winchester, MA 01890
Year Built:
--
HOA:
None
$2,500/mo
1
Bed
1/1
Bath
800
Sqft
253 Swanton Street #Rear
Winchester, MA 01890
Year Built:
--
HOA:
None
$2,200/mo
1
Bed
1
Bath
606
Sqft
200 Swanton St #428
Winchester, MA 01890
Year Built:
1966
HOA:
None
$1,880/mo
0
Beds
1
Bath
350
Sqft
200 Swanton #704
Winchester, MA 01890
Year Built:
--
HOA:
None
$1,800/mo
0
Beds
1
Bath
394
Sqft
200 Swanton #502
Winchester, MA 01890
Year Built:
1966
HOA:
None
Showing 1 - 68 of 68 Results
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