75 Homes for Sale in Winchester
$4,449,000
5
Beds
5/1
Baths
6,526
Sqft
4 Dartmouth St
Winchester, MA 01890
Year Built:
1935
HOA:
None
$3,600,000
6
Beds
6/1
Baths
7,400
Sqft
2 Atherton Rd
Winchester, MA 01890
Year Built:
2025
HOA:
None
$3,600,000
6
Beds
7
Baths
8,866
Sqft
20 Amberwood Dr
Winchester, MA 01890
Year Built:
2024
HOA:
None
$3,475,000
7
Beds
3/3
Baths
7,043
Sqft
2 Everett Ave
Winchester, MA 01890
Year Built:
1916
HOA:
None
$3,379,000
7
Beds
7/1
Baths
8,540
Sqft
37 Mayflower Road
Winchester, MA 01890
Year Built:
2009
HOA:
None
$3,299,000
7
Beds
7/1
Baths
7,226
Sqft
1 Plymouth Rd
Winchester, MA 01890
Year Built:
2025
HOA:
None
$3,250,000
5
Beds
5/1
Baths
6,500
Sqft
8 Priscilla Ln
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
$3,099,000
6
Beds
8
Baths
7,168
Sqft
4 Lawrence St
Winchester, MA 01890
Year Built:
1903
HOA:
None
$2,950,000
5
Beds
4/1
Baths
5,202
Sqft
74 Wedgemere Avenue
Winchester, MA 01890
Year Built:
1938
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
$2,675,000
6
Beds
3/2
Baths
4,540
Sqft
47 Yale Street
Winchester, MA 01890
Year Built:
1920
HOA:
None
$2,599,000
5
Beds
4
Baths
5,083
Sqft
53 Winford Way
Winchester, MA 01890
Year Built:
2025
HOA:
None
$2,599,000
5
Beds
3/1
Baths
5,230
Sqft
78 Bacon Street
Winchester, MA 01890
Year Built:
1910
HOA:
None
$2,549,000
4
Beds
3/1
Baths
4,403
Sqft
50 Brooks Street
Winchester, MA 01890
Year Built:
1988
HOA:
None
$2,200,000
5
Beds
3/1
Baths
4,744
Sqft
30 Rangeley Road
Winchester, MA 01890
Year Built:
1929
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
6
Beds
4/1
Baths
6,900
Sqft
16 Glenwood Ave
Winchester, MA 01890
Year Built:
1966
HOA:
None
$2,000,000
6
Beds
3/2
Baths
3,403
Sqft
6 Ivy Circle
Winchester, MA 01890
Year Built:
1966
HOA:
None
$1,999,000
5
Beds
2/2
Baths
3,136
Sqft
22 Hollywood Rd
Winchester, MA 01890
Year Built:
1962
HOA:
None
$1,925,000
5
Beds
2/2
Baths
3,315
Sqft
8 Hawthorne Rd
Winchester, MA 01890
Year Built:
1959
HOA:
None
$1,899,000
5
Beds
2/1
Baths
3,278
Sqft
105 Thornberry Rd
Winchester, MA 01890
Year Built:
1971
HOA:
None
$1,799,000
4
Beds
3
Baths
3,366
Sqft
94 Johnson Road
Winchester, MA 01890
Year Built:
1971
HOA:
None
$1,799,000
3
Beds
3/1
Baths
3,010
Sqft
1 Town Way
Winchester, MA 01890
Year Built:
2026
HOA:
None
$1,699,000
3
Beds
2/1
Baths
2,992
Sqft
18 Grayson Rd
Winchester, MA 01890
Year Built:
1931
HOA:
None
$1,495,000
4
Beds
2/1
Baths
2,605
Sqft
7 Sherman Place
Winchester, MA 01890
Year Built:
2005
HOA:
None
$1,495,000
4
Beds
2/1
Baths
2,605
Sqft
7 Sherman Place #7
Winchester, MA 01890
Year Built:
2005
HOA:
None
$1,300,000
4
Beds
2/1
Baths
2,666
Sqft
465 Washington St #465
Winchester, MA 01890
Year Built:
2017
HOA:
None
$1,300,000
4
Beds
2/1
Baths
2,666
Sqft
465 Washington St
Winchester, MA 01890
Year Built:
2017
HOA:
None
$1,260,000
3
Beds
3/1
Baths
2,420
Sqft
129 Washington St #129
Winchester, MA 01890
Year Built:
1890
HOA:
None
$1,225,000
3
Beds
2/1
Baths
2,235
Sqft
53 Lake Street
Winchester, MA 01890
Year Built:
1864
HOA:
None
$1,199,000
5
Beds
1/1
Bath
2,688
Sqft
6 Hancock St
Winchester, MA 01890
Year Built:
1890
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
2
Beds
1/1
Bath
1,365
Sqft
83 Church Street #15
Winchester, MA 01890
Year Built:
1983
HOA:
None
$999,000
4
Beds
2
Baths
2,085
Sqft
41 Cross St
Winchester, MA 01890
Year Built:
1860
HOA:
None
$929,900
4
Beds
2
Baths
1,938
Sqft
380 Cross Street
Winchester, MA 01890
Year Built:
1939
HOA:
None
$799,000
3
Beds
1
Bath
1,245
Sqft
55 Brookside Ave
Winchester, MA 01890
Year Built:
1940
HOA:
None
$688,000
2
Beds
2
Baths
1,025
Sqft
666 Main St #315
Winchester, MA 01890
Year Built:
1982
HOA:
None
$659,000
3
Beds
1/1
Bath
1,331
Sqft
18 Bradford Road #18
Winchester, MA 01890
Year Built:
1963
HOA:
None
$505,000
2
Beds
1
Bath
822
Sqft
200 Swanton St #303
Winchester, MA 01890
Year Built:
1966
HOA:
None
$414,500
2
Beds
1
Bath
1,121
Sqft
22 Arthur St #22
Winchester, MA 01890
Year Built:
1897
HOA:
None
$400,000
2
Beds
1
Bath
810
Sqft
200 Swanton Street #T35
Winchester, MA 01890
Year Built:
1966
HOA:
None
$379,900
1
Bed
1
Bath
606
Sqft
200 Swanton St #318
Winchester, MA 01890
Year Built:
1966
HOA:
None
$375,000
1
Bed
1
Bath
606
Sqft
200 Swanton St #228
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
$220,000
2
Beds
1
Bath
1,424
Sqft
886 Keene Rd
Winchester, NH 03470
Year Built:
1875
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
$11,500/mo
7
Beds
3/1
Baths
3,300
Sqft
34 Glen Road
Winchester, MA 01890
Year Built:
--
HOA:
None
$10,000/mo
6
Beds
4/1
Baths
6,583
Sqft
282 High Street
Winchester, MA 01890
Year Built:
1995
HOA:
None
$8,000/mo
3
Beds
2
Baths
3,500
Sqft
31 Fells Road
Winchester, MA 01890
Year Built:
--
HOA:
None
$7,900/mo
4
Beds
2/1
Baths
4,300
Sqft
18 Grant Road
Winchester, MA 01890
Year Built:
--
HOA:
None
$6,500/mo
4
Beds
4
Baths
3,436
Sqft
37 Emerson Rd
Winchester, MA 01890
Year Built:
1946
HOA:
None
$6,000/mo
3
Beds
2/1
Baths
3,500
Sqft
40 Church St #B
Winchester, MA 01890
Year Built:
2015
HOA:
None
$5,500/mo
3
Beds
3/1
Baths
3,090
Sqft
17 Cardinal St #17
Winchester, MA 01890
Year Built:
2015
HOA:
None
$5,500/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
1/1
Bath
1,657
Sqft
17 Russell Rd
Winchester, MA 01890
Year Built:
--
HOA:
None
$4,900/mo
3
Beds
1/1
Bath
2,754
Sqft
16 Nathaniel Rd
Winchester, MA 01890
Year Built:
1950
HOA:
None
$4,850/mo
4
Beds
1/1
Bath
1,700
Sqft
488 Washington Street
Winchester, MA 01890
Year Built:
1927
HOA:
None
$4,450/mo
3
Beds
2/2
Baths
2,800
Sqft
11 Highlandview Ave #11
Winchester, MA 01890
Year Built:
--
HOA:
None
$4,400/mo
2
Beds
1
Bath
1,200
Sqft
67 Church St #67
Winchester, MA 01890
Year Built:
--
HOA:
None
$4,150/mo
4
Beds
2
Baths
1,967
Sqft
10-12 Webster St #1
Winchester, MA 01890
Year Built:
--
HOA:
None
$4,100/mo
2
Beds
1
Bath
1,000
Sqft
63 Holland St #63
Winchester, MA 01890
Year Built:
--
HOA:
None
$3,600/mo
3
Beds
2
Baths
2,400
Sqft
16 Richardson St #16
Winchester, MA 01890
Year Built:
1930
HOA:
None
$3,400/mo
2
Beds
2/1
Baths
1,332
Sqft
7 Conant Rd #11
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
$3,150/mo
2
Beds
1
Bath
1,172
Sqft
31 Irving St #1
Winchester, MA 01890
Year Built:
1988
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 Street #T-37
Winchester, MA 01890
Year Built:
--
HOA:
None
$2,600/mo
2
Beds
1
Bath
822
Sqft
200 Swanton St #237
Winchester, MA 01890
Year Built:
--
HOA:
None
$2,600/mo
2
Beds
1
Bath
800
Sqft
200 Swanton St #635
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
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