80 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
$3,895,000
7
Beds
5/3
Baths
7,587
Sqft
25 Wedgemere Ave
Winchester, MA 01890
Year Built:
2010
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
4/1
Baths
5,876
Sqft
5 Stratford Road
Winchester, MA 01890
Year Built:
1870
HOA:
None
$3,475,000
5
Beds
3/1
Baths
5,632
Sqft
80 Arlington Street
Winchester, MA 01890
Year Built:
1973
HOA:
None
$3,249,000
6
Beds
6/1
Baths
6,028
Sqft
44 Cabot Street
Winchester, MA 01890
Year Built:
2025
HOA:
None
$3,175,000
5
Beds
4/1
Baths
5,386
Sqft
21 Fernway
Winchester, MA 01890
Year Built:
1963
HOA:
None
$3,175,000
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
5
Beds
4/1
Baths
6,904
Sqft
11 Fieldstone Drive
Winchester, MA 01890
Year Built:
1989
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
7
Beds
5/1
Baths
5,864
Sqft
10 Sheffield Road
Winchester, MA 01890
Year Built:
1916
HOA:
None
$2,890,000
5
Beds
4/2
Baths
5,354
Sqft
8 Chestnut St
Winchester, MA 01890
Year Built:
1850
HOA:
None
$2,850,000
6
Beds
5/2
Baths
6,968
Sqft
14 Nassau Drive
Winchester, MA 01890
Year Built:
2002
HOA:
None
$2,650,000
4
Beds
3
Baths
4,276
Sqft
8 Tanglewood Lane
Winchester, MA 01890
Year Built:
1985
HOA:
None
$2,599,000
4
Beds
4/1
Baths
5,501
Sqft
15 Churchill Road
Winchester, MA 01890
Year Built:
2025
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
7
Beds
5/1
Baths
4,829
Sqft
89 Wildwood St
Winchester, MA 01890
Year Built:
2025
HOA:
None
$2,399,000
5
Beds
3/1
Baths
5,077
Sqft
276 High Street
Winchester, MA 01890
Year Built:
1992
HOA:
None
$2,349,000
4
Beds
3/1
Baths
4,959
Sqft
5 Azalea Rd
Winchester, MA 01890
Year Built:
1980
HOA:
None
$2,299,000
6
Beds
3/1
Baths
4,667
Sqft
9 Prospect St
Winchester, MA 01890
Year Built:
1895
HOA:
None
$2,250,000
5
Beds
5
Baths
5,000
Sqft
1 Fox Hunt Ln
Winchester, MA 01890
Year Built:
1968
HOA:
None
$2,249,900
4
Beds
3/1
Baths
4,023
Sqft
19 Sussex Rd
Winchester, MA 01890
Year Built:
1998
HOA:
None
$2,099,000
6
Beds
3/1
Baths
4,696
Sqft
5 Squire Rd
Winchester, MA 01890
Year Built:
2016
HOA:
None
$2,050,000
5
Beds
3/1
Baths
3,874
Sqft
4 Worthen Road
Winchester, MA 01890
Year Built:
1932
HOA:
None
$1,799,999
3
Beds
2/1
Baths
3,002
Sqft
44 Amberwood Drive
Winchester, MA 01890
Year Built:
1983
HOA:
None
$1,775,000
5
Beds
3/1
Baths
3,150
Sqft
19 Pilgrim Dr
Winchester, MA 01890
Year Built:
1961
HOA:
None
$1,769,000
5
Beds
3/1
Baths
3,478
Sqft
10 Olde Lyme Road
Winchester, MA 01890
Year Built:
1960
HOA:
None
$1,625,000
3
Beds
3/1
Baths
4,228
Sqft
7 Wainwright Road #55
Winchester, MA 01890
Year Built:
1987
HOA:
None
$1,499,000
3
Beds
2/1
Baths
2,605
Sqft
14 Hillside Ave
Winchester, MA 01890
Year Built:
1870
HOA:
None
$1,449,900
5
Beds
2
Baths
3,033
Sqft
7 Thornberry Road
Winchester, MA 01890
Year Built:
1957
HOA:
None
$1,389,000
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
$1,345,000
3
Beds
2
Baths
2,238
Sqft
49 Lincoln Street
Winchester, MA 01890
Year Built:
1905
HOA:
None
$1,329,000
3
Beds
2
Baths
1,884
Sqft
147 Highland Ave
Winchester, MA 01890
Year Built:
1919
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
$1,295,000
4
Beds
1/1
Bath
2,202
Sqft
71 Woodside Rd
Winchester, MA 01890
Year Built:
1927
HOA:
None
$1,199,900
4
Beds
2/1
Baths
2,302
Sqft
518 Washington St
Winchester, MA 01890
Year Built:
1915
HOA:
None
$1,199,000
3
Beds
2
Baths
1,536
Sqft
8 Garfield Avenue
Winchester, MA 01890
Year Built:
1940
HOA:
None
$1,199,000
3
Beds
1/1
Bath
1,573
Sqft
18 Brookside Avenue
Winchester, MA 01890
Year Built:
1910
HOA:
None
$1,010,000
3
Beds
1
Bath
1,425
Sqft
571 Washington St
Winchester, MA 01890
Year Built:
1920
HOA:
None
$960,000
2
Beds
2
Baths
1,540
Sqft
6 Francis Circuit #6
Winchester, MA 01890
Year Built:
1875
HOA:
None
$859,000
2
Beds
1
Bath
1,123
Sqft
22 Grove Place #4
Winchester, MA 01890
Year Built:
1986
HOA:
None
$689,000
2
Beds
2
Baths
1,160
Sqft
7 Conant Rd #23
Winchester, MA 01890
Year Built:
2000
HOA:
None
$679,900
2
Beds
2
Baths
1,168
Sqft
7 Conant Rd #20
Winchester, MA 01890
Year Built:
2000
HOA:
None
$674,900
2
Beds
1
Bath
1,084
Sqft
20 Arthur St #20
Winchester, MA 01890
Year Built:
1897
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
$11,000/mo
6
Beds
4/1
Baths
6,500
Sqft
52 North Border Rd.
Winchester, MA 01890
Year Built:
2008
HOA:
None
$10,000/mo
7
Beds
3/1
Baths
3,300
Sqft
34 Glen Road
Winchester, MA 01890
Year Built:
--
HOA:
None
$9,800/mo
5
Beds
4/1
Baths
5,016
Sqft
22 Amberwood Dr
Winchester, MA 01890
Year Built:
1974
HOA:
None
$9,500/mo
6
Beds
4/1
Baths
3,118
Sqft
23 Jefferson Road
Winchester, MA 01890
Year Built:
1929
HOA:
None
$8,900/mo
4
Beds
4
Baths
4,650
Sqft
31 Coolidge St
Winchester, MA 01890
Year Built:
1980
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
$7,300/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
$6,900/mo
4
Beds
3/1
Baths
2,500
Sqft
37 Rumford St #37
Winchester, MA 01890
Year Built:
2012
HOA:
None
$5,500/mo
4
Beds
3/1
Baths
2,500
Sqft
48 Spruce #48
Winchester, MA 01890
Year Built:
--
HOA:
None
$5,200/mo
4
Beds
2/1
Baths
2,200
Sqft
42 Spruce #42
Winchester, MA 01890
Year Built:
2000
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
$4,500/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
1
Bath
1,200
Sqft
67 Church #67
Winchester, MA 01890
Year Built:
--
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
2
Beds
1
Bath
1,100
Sqft
40 Florence Street #40
Winchester, MA 01890
Year Built:
1915
HOA:
None
$3,200/mo
2
Beds
2/1
Baths
1,332
Sqft
7 Conant Rd #11
Winchester, MA 01890
Year Built:
--
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
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
1,068
Sqft
359 Washington St #359
Winchester, MA 01890
Year Built:
--
HOA:
None
$2,800/mo
2
Beds
2
Baths
1,452
Sqft
273 Cross St #273
Winchester, MA 01890
Year Built:
1960
HOA:
None
$2,700/mo
2
Beds
1
Bath
822
Sqft
200 Swanton St #205
Winchester, MA 01890
Year Built:
--
HOA:
None
$2,680/mo
2
Beds
1
Bath
833
Sqft
200 Swanton St #239
Winchester, MA 01890
Year Built:
--
HOA:
None
$2,500/mo
1
Bed
1
Bath
602
Sqft
200 Swanton St #L25
Winchester, MA 01890
Year Built:
--
HOA:
None
$2,350/mo
1
Bed
1
Bath
775
Sqft
35 Vine Street #401
Winchester, MA 01890
Year Built:
--
HOA:
None
$2,100/mo
1
Bed
1
Bath
606
Sqft
200 Swanton St #428
Winchester, MA 01890
Year Built:
1966
HOA:
None
$1,650/mo
0
Beds
1
Bath
394
Sqft
200 Swanton St #502
Winchester, MA 01890
Year Built:
1966
HOA:
None
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