73 Homes for Sale in Winchester
$4,250,000
5
Beds
3/1
Baths
4,484
Sqft
9 Lakeview Terrace
Winchester, MA 01890
Year Built:
1905
HOA:
None
$3,999,000
6
Beds
4/1
Baths
6,367
Sqft
40 Foxcroft Rd
Winchester, MA 01890
Year Built:
2025
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
$3,599,000
6
Beds
4/1
Baths
5,876
Sqft
5 Stratford Road
Winchester, MA 01890
Year Built:
1870
HOA:
None
$3,598,000
6
Beds
7
Baths
8,866
Sqft
20 Amberwood Dr
Winchester, MA 01890
Year Built:
2024
HOA:
None
$3,475,000
5
Beds
3/1
Baths
5,632
Sqft
80 Arlington Street
Winchester, MA 01890
Year Built:
1973
HOA:
None
$3,399,000
5
Beds
4/1
Baths
5,250
Sqft
4 Norwood St
Winchester, MA 01890
Year Built:
1870
HOA:
None
$3,249,000
6
Beds
5
Baths
7,005
Sqft
18 Wickham Road
Winchester, MA 01890
Year Built:
2022
HOA:
None
$3,249,000
6
Beds
6/1
Baths
6,028
Sqft
44 Cabot Street
Winchester, MA 01890
Year Built:
2025
HOA:
None
$3,099,000
6
Beds
3/1
Baths
5,238
Sqft
54 Wedgemere Avenue
Winchester, MA 01890
Year Built:
1915
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
$2,899,000
7
Beds
5/1
Baths
5,864
Sqft
10 Sheffield Road
Winchester, MA 01890
Year Built:
1916
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
$2,599,000
6
Beds
4/1
Baths
5,824
Sqft
107 Cambridge Street
Winchester, MA 01890
Year Built:
1911
HOA:
None
$2,550,000
5
Beds
4/1
Baths
3,800
Sqft
19 Laurel Hill Ln
Winchester, MA 01890
Year Built:
1954
HOA:
None
$2,499,000
6
Beds
4/1
Baths
4,200
Sqft
14 Grant Rd
Winchester, MA 01890
Year Built:
2025
HOA:
None
$2,499,000
7
Beds
5/1
Baths
4,829
Sqft
89 Wildwood St
Winchester, MA 01890
Year Built:
2025
HOA:
None
$2,399,000
6
Beds
3/2
Baths
3,728
Sqft
6 Ivy Cir
Winchester, MA 01890
Year Built:
2025
HOA:
None
$2,349,900
5
Beds
5
Baths
3,940
Sqft
17 Wagon Wheel Road
Winchester, MA 01890
Year Built:
1983
HOA:
None
$2,349,000
5
Beds
3/1
Baths
4,959
Sqft
5 Azalea Rd
Winchester, MA 01890
Year Built:
1980
HOA:
None
$2,295,000
6
Beds
5/1
Baths
5,791
Sqft
58 Bacon Street
Winchester, MA 01890
Year Built:
1924
HOA:
None
$2,250,000
5
Beds
5
Baths
5,000
Sqft
1 Fox Hunt Ln
Winchester, MA 01890
Year Built:
1968
HOA:
None
$2,239,000
5
Beds
4/1
Baths
4,798
Sqft
61 Grove Street
Winchester, MA 01890
Year Built:
2017
HOA:
None
$2,070,000
5
Beds
3/1
Baths
4,378
Sqft
4 Fieldstone Dr
Winchester, MA 01890
Year Built:
1987
HOA:
None
$1,999,900
5
Beds
3/1
Baths
3,607
Sqft
4 Winslow Rd
Winchester, MA 01890
Year Built:
1895
HOA:
None
$1,990,000
4
Beds
4/1
Baths
4,474
Sqft
4 Chestnut St
Winchester, MA 01890
Year Built:
1959
HOA:
None
$1,900,000
4
Beds
3/2
Baths
5,361
Sqft
4 Aricia Ln
Winchester, MA 01890
Year Built:
1984
HOA:
None
$1,765,300
3
Beds
2/1
Baths
3,002
Sqft
44 Amberwood Drive
Winchester, MA 01890
Year Built:
1983
HOA:
None
$1,449,900
5
Beds
2
Baths
3,033
Sqft
7 Thornberry Road
Winchester, MA 01890
Year Built:
1957
HOA:
None
$1,349,900
5
Beds
2
Baths
1,706
Sqft
35 Harvard Street
Winchester, MA 01890
Year Built:
1880
HOA:
None
$1,349,000
3
Beds
1/1
Bath
3,335
Sqft
10 Girard Rd
Winchester, MA 01890
Year Built:
1953
HOA:
None
$1,299,000
3
Beds
3/1
Baths
2,136
Sqft
162 Swanton Street #162
Winchester, MA 01890
Year Built:
2025
HOA:
None
$1,299,000
3
Beds
2
Baths
1,884
Sqft
147 Highland Ave
Winchester, MA 01890
Year Built:
1919
HOA:
None
$1,099,000
3
Beds
2
Baths
1,536
Sqft
8 Garfield Avenue
Winchester, MA 01890
Year Built:
1940
HOA:
None
$764,900
2
Beds
2/1
Baths
1,435
Sqft
171 Swanton St #12
Winchester, MA 01890
Year Built:
1984
HOA:
None
$709,999
2
Beds
2
Baths
1,170
Sqft
666 Main St #206
Winchester, MA 01890
Year Built:
1982
HOA:
None
$625,900
2
Beds
1
Bath
1,084
Sqft
20 Arthur St #20
Winchester, MA 01890
Year Built:
1897
HOA:
None
$625,000
2
Beds
1/1
Bath
1,464
Sqft
60 Lake St #I
Winchester, MA 01890
Year Built:
1976
HOA:
None
$625,000
2
Beds
1/1
Bath
1,157
Sqft
29 Vine Street #8
Winchester, MA 01890
Year Built:
1980
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
6
Beds
7
Baths
8,866
Sqft
20 Amberwood Dr
Winchester, MA 01890
Year Built:
2024
HOA:
None
$14,000/mo
5
Beds
4/1
Baths
5,250
Sqft
4 Norwood St #4
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
4
Beds
3/1
Baths
3,500
Sqft
35 Thornberry Road
Winchester, MA 01890
Year Built:
2010
HOA:
None
$9,500/mo
6
Beds
4/1
Baths
3,118
Sqft
23 Jefferson Road
Winchester, MA 01890
Year Built:
1929
HOA:
None
$9,500/mo
7
Beds
3/1
Baths
3,300
Sqft
34 Glen Road
Winchester, MA 01890
Year Built:
--
HOA:
None
$9,400/mo
5
Beds
4/1
Baths
5,016
Sqft
22 Amberwood Dr
Winchester, MA 01890
Year Built:
1974
HOA:
None
$7,500/mo
3
Beds
2/1
Baths
2,900
Sqft
846 Main Street #III
Winchester, MA 01890
Year Built:
2020
HOA:
None
$7,450/mo
4
Beds
4
Baths
4,650
Sqft
31 Coolidge St
Winchester, MA 01890
Year Built:
1980
HOA:
None
$7,000/mo
4
Beds
2/1
Baths
2,800
Sqft
72 Holland #72
Winchester, MA 01890
Year Built:
2021
HOA:
None
$7,000/mo
3
Beds
2/1
Baths
2,900
Sqft
846 Main Street #IV
Winchester, MA 01890
Year Built:
2020
HOA:
None
$6,800/mo
4
Beds
3/1
Baths
2,500
Sqft
37 Rumford St #37
Winchester, MA 01890
Year Built:
2012
HOA:
None
$6,000/mo
3
Beds
2/1
Baths
1,836
Sqft
3 Wainwright Rd. #SFAM
Winchester, MA 01890
Year Built:
--
HOA:
None
$5,995/mo
2
Beds
2/1
Baths
2,173
Sqft
23 Elmwood Ave #C
Winchester, MA 01890
Year Built:
1985
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
$4,800/mo
3
Beds
1/1
Bath
1,000
Sqft
24 Clematis St #2
Winchester, MA 01890
Year Built:
--
HOA:
None
$4,200/mo
3
Beds
2/1
Baths
1,823
Sqft
171 Swanton Street #63
Winchester, MA 01890
Year Built:
1985
HOA:
None
$3,600/mo
4
Beds
1/2
Bath
1,500
Sqft
238 Washington #2
Winchester, MA 01890
Year Built:
1927
HOA:
None
$3,600/mo
3
Beds
2
Baths
1,200
Sqft
9 Mount Vernon Street #C
Winchester, MA 01890
Year Built:
--
HOA:
None
$3,500/mo
3
Beds
1
Bath
1,400
Sqft
534 Washington St #2
Winchester, MA 01890
Year Built:
1932
HOA:
None
$3,200/mo
2
Beds
1/1
Bath
1,331
Sqft
29 Vine Street #3
Winchester, MA 01890
Year Built:
--
HOA:
None
$3,200/mo
2
Beds
1
Bath
1,100
Sqft
40 Florence Street #40
Winchester, MA 01890
Year Built:
1915
HOA:
None
$3,000/mo
3
Beds
2
Baths
1,300
Sqft
17 Irving Street #3
Winchester, MA 01890
Year Built:
1898
HOA:
None
$3,000/mo
2
Beds
1
Bath
800
Sqft
37-39 Spruce Street #37
Winchester, MA 01890
Year Built:
--
HOA:
None
$3,000/mo
2
Beds
1
Bath
1,024
Sqft
247 Washington St #13
Winchester, MA 01890
Year Built:
1975
HOA:
None
$2,800/mo
2
Beds
2
Baths
1,452
Sqft
273 Cross St #273
Winchester, MA 01890
Year Built:
1960
HOA:
None
$2,600/mo
2
Beds
1
Bath
833
Sqft
200 Swanton St #239
Winchester, MA 01890
Year Built:
--
HOA:
None
$2,600/mo
2
Beds
1
Bath
986
Sqft
63-65 Harvard Street #1
Winchester, MA 01890
Year Built:
1880
HOA:
None
$2,000/mo
1
Bed
1
Bath
602
Sqft
200 Swanton St #L25
Winchester, MA 01890
Year Built:
--
HOA:
None
$1,700/mo
1
Bed
1
Bath
385
Sqft
200 Swanton St #738
Winchester, MA 01890
Year Built:
--
HOA:
None
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