93 results in search
42 photos
15 Vinson Circle Winchester MA 01890
$18,000,000
Beds: 6
Baths: 6.5
Sq Ft: 10,000
Days on Market: 45
Updated 6 Minutes Ago
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38 photos
4 Dartmouth Winchester MA 01890
$4,299,000
Beds: 5
Baths: 5.5
Sq Ft: 6,526
Days on Market: 66
Updated 6 Minutes Ago
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42 photos
724 Main St Winchester MA 01890
$4,000,000
Beds:
Baths:
Sq Ft: 7,010
Days on Market: 53
Updated 6 Minutes Ago
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40 photos
15 Foxcroft Rd Winchester MA 01890
$3,799,000
Beds: 8
Baths: 5
Sq Ft: 7,081
Days on Market: 25
Updated 6 Minutes Ago
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36 photos
11 Viking Road Winchester MA 01890
$3,600,000
Beds: 7
Baths: 7.5
Sq Ft: 7,429
Days on Market: 109
Open: 11/15/26 2:30 PM - 3:30 PM
Updated 6 Minutes Ago
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42 photos
25 Canterbury Road Winchester MA 01890
$3,499,000
Beds: 6
Baths: 5.5
Sq Ft: 6,327
Days on Market: 6
Open: 11/15/26 12 PM - 1:30 PM
Updated 6 Minutes Ago
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28 photos
1 Plymouth Rd. Winchester MA 01890
$3,299,000
Beds: 7
Baths: 7.5
Sq Ft: 7,226
Days on Market: 45
Updated 6 Minutes Ago
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42 photos
7 Hutchinson Road Winchester MA 01890
$3,295,000
-$155,000
Beds: 6
Baths: 4.5
Sq Ft: 5,735
Days on Market: 97
Updated 6 Minutes Ago
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41 photos
30 Willowdale Rd Winchester MA 01890
$3,200,000
Beds: 8
Baths: 6.5
Sq Ft: 5,750
Days on Market: 61
Open: 11/15/26 1 PM - 2:30 PM
Updated 6 Minutes Ago
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42 photos
37 Mayflower Road Winchester MA 01890
$3,149,000
Beds: 7
Baths: 7.5
Sq Ft: 8,540
Days on Market: 68
Updated 6 Minutes Ago
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10 photos
5 Forest Cir Winchester MA 01890
$2,999,000
Beds: 5
Baths: 4.5
Sq Ft: 4,900
Days on Market: 23
Updated 6 Minutes Ago
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41 photos
9 Albamont Road Winchester MA 01890
$2,995,000
-$205,000
Beds: 6
Baths: 5.5
Sq Ft: 6,100
Days on Market: 256
Updated 6 Minutes Ago
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41 photos
18 Surrey Road Winchester MA 01890
$2,950,000
Beds: 6
Baths: 4
Sq Ft: 4,752
Days on Market: 27
Updated 6 Minutes Ago
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30 photos
14 Nassau Drive Winchester MA 01890
$2,750,000
Beds: 6
Baths: 6
Sq Ft: 6,968
Days on Market: 215
Updated 6 Minutes Ago
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32 photos
18 Middlesex St Winchester MA 01890
$2,650,000
Beds: 4
Baths: 4.5
Sq Ft: 5,233
Days on Market: 24
Open: 11/15/26 11:30 AM - 1 PM
Updated 6 Minutes Ago
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42 photos
54 Squire Road Winchester MA 01890
$2,299,000
Beds: 4
Baths: 4.5
Sq Ft: 4,450
Days on Market: 96
Open: 11/15/26 12 PM - 1:30 PM
Updated 6 Minutes Ago
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42 photos
7 Lakeview Terrace Winchester MA 01890
$2,250,000
-$150,000
Beds: 6
Baths: 3
Sq Ft: 3,534
Days on Market: 60
Open: 11/15/26 3 PM - 4 PM
Updated 6 Minutes Ago
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41 photos
276 High Street Winchester MA 01890
$2,195,000
Beds: 5
Baths: 3.5
Sq Ft: 5,006
Days on Market: 223
Open: 11/15/26 12 PM - 1 PM
Updated 6 Minutes Ago
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37 photos
9 Plymouth Rd Winchester MA 01890
$2,175,000
Beds: 5
Baths: 3
Sq Ft: 4,071
Days on Market: 132
Updated 6 Minutes Ago
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40 photos
19 Hancock Street Winchester MA 01890
$2,149,000
-$50,000
Beds: 4
Baths: 3.5
Sq Ft: 3,570
Days on Market: 68
Open: 11/15/26 1:30 PM - 3 PM
Updated 6 Minutes Ago
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36 photos
6 Ivy Circle Winchester MA 01890
$2,100,000
Beds: 6
Baths: 4
Sq Ft: 3,403
Days on Market: 199
Open: 11/15/26 1:15 PM - 2:15 PM
Updated 6 Minutes Ago
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42 photos
21 Amberwood Dr Winchester MA 01890
$1,999,000
Beds: 5
Baths: 3.5
Sq Ft: 4,063
Days on Market: 39
Open: 11/15/26 11 AM - 12:30 PM
Updated 6 Minutes Ago
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37 photos
17 Churchill Rd Winchester MA 01890
$1,749,000
Beds: 5
Baths: 3.5
Sq Ft: 3,508
Days on Market: 68
Open: 11/15/26 12 PM - 1 PM
Updated 6 Minutes Ago
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36 photos
85 High Street Winchester MA 01890
$1,749,000
-$150,000
Beds: 4
Baths: 2.5
Sq Ft: 3,757
Days on Market: 16
Updated 6 Minutes Ago
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41 photos
1 Town Way Winchester MA 01890
$1,744,000
-$5,000
Beds: 3
Baths: 3.5
Sq Ft: 3,010
Days on Market: 110
Open: 11/15/26 11:30 AM - 1 PM
Updated 6 Minutes Ago
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42 photos
117 Highland Winchester MA 01890
$1,650,000
Beds: 5
Baths: 3.5
Sq Ft: 3,722
Days on Market: 67
Updated 6 Minutes Ago
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40 photos
1 Overlook Way Winchester MA 01890
$1,650,000
-$100,000
Beds: 4
Baths: 2.5
Sq Ft: 3,604
Days on Market: 53
Updated 6 Minutes Ago
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10 photos
9 Watson Pl Winchester MA 01890
$1,599,000
Beds: 3
Baths: 2.5
Sq Ft: 1,920
Days on Market: 9
Updated 6 Minutes Ago
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41 photos
50 Holland Street Winchester MA 01890
$1,549,000
Beds: 3
Baths: 2.5
Sq Ft: 2,640
Days on Market: 109
Open: 11/15/26 12 PM - 1 PM
Updated 6 Minutes Ago
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6 photos
67-69 Hemingway St Winchester MA 01890
$1,450,000
Beds: 8
Baths: 5
Sq Ft: 6,200
Days on Market: 23
Updated 6 Minutes Ago
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Style
- Antique
- Bungalow
- Cape
- Colonial
- Colonial Revival
- Contemporary
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- Shingle
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Subdivision
- Cox Road / High St Extension neighborhood
- Downtown neighborhood location
- East Side
- Flats
- Lakeview/Ravenscroft
- Middlesex / downtown
- Wedgemere
- West Side
- West Side Ambrose Neighborhood
- West side, on a cul de sac
- Winchester town center