Winchester MA Listings
87 results in search
42 photos
4 Dartmouth St Winchester MA 01890
$4,699,000
Beds: 5
Baths: 5.5
Sq Ft: 6,526
Days on Market: 22
Updated 11 Minutes Ago
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42 photos
9 Lakeview Terrace Winchester MA 01890
$3,750,000
Beds: 6
Baths: 3.5
Sq Ft: 4,484
Days on Market: 287
Updated 11 Minutes Ago
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42 photos
40 Foxcroft Rd Winchester MA 01890
$3,750,000
Beds: 6
Baths: 4.5
Sq Ft: 6,460
Days on Market: 15
Open: 3/28/26 12 PM - 1:30 PM,
3/29/26 12 PM - 1:30 PM
Updated 11 Minutes Ago
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41 photos
2 Everett Ave Winchester MA 01890
$3,747,000
Beds: 7
Baths: 4.5
Sq Ft: 7,043
Days on Market: 8
Updated 11 Minutes Ago
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36 photos
20 Amberwood Dr Winchester MA 01890
$3,600,000
Beds: 6
Baths: 7
Sq Ft: 8,866
Days on Market: 207
Open: 3/29/26 12:30 PM - 1:30 PM
Updated 11 Minutes Ago
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42 photos
37 Mayflower Road Winchester MA 01890
$3,537,000
Beds: 7
Baths: 7.5
Sq Ft: 8,540
Days on Market: 46
Open: 3/29/26 12 PM - 1 PM
Updated 11 Minutes Ago
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42 photos
54 Johnson Rd Winchester MA 01890
$3,499,000
Beds: 5
Baths: 7.5
Sq Ft: 6,899
Days on Market: 51
Updated 11 Minutes Ago
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39 photos
15 Mayflower Rd Winchester MA 01890
$3,425,000
Beds: 7
Baths: 7.5
Sq Ft: 7,226
Days on Market: 51
Open: 3/28/26 1 PM - 2:30 PM
Updated 11 Minutes Ago
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10 photos
9 Albamont Road Winchester MA 01890
$3,400,000
Beds: 6
Baths: 5.5
Sq Ft: 6,100
Days on Market: 23
Updated 11 Minutes Ago
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31 photos
25 Myopia Road Winchester MA 01890
$3,390,000
Beds: 4
Baths: 3.5
Sq Ft: 4,847
Days on Market: 60
Open: 3/29/26 1:45 PM - 3 PM
Updated 11 Minutes Ago
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42 photos
10 Dartmouth Street Winchester MA 01890
$3,299,000
Beds: 5
Baths: 3
Sq Ft: 4,028
Days on Market: 9
Open: 3/28/26 1:30 PM - 2:30 PM,
3/29/26 11 AM - 12:30 PM
Updated 11 Minutes Ago
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39 photos
27 Everett Ave Winchester MA 01890
$3,290,000
Beds: 6
Baths: 5.5
Sq Ft: 7,431
Days on Market: 71
Open: 3/28/26 12 PM - 1:30 PM
Updated 11 Minutes Ago
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13 photos
39 Town Way Winchester MA 01890
$3,199,000
Beds: 6
Baths: 6
Sq Ft: 5,709
Days on Market: 168
Updated 11 Minutes Ago
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42 photos
45 Bacon Street Winchester MA 01890
$2,965,000
Beds: 7
Baths: 7
Sq Ft: 7,043
Days on Market: 30
Updated 11 Minutes Ago
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42 photos
19 Town Way Winchester MA 01890
$2,899,000
Beds: 5
Baths: 5.5
Sq Ft: 5,257
Days on Market: 129
Updated 11 Minutes Ago
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16 photos
53 Winford Way Winchester MA 01890
$2,799,000
Beds: 5
Baths: 4
Sq Ft: 5,083
Days on Market: 25
Open: 3/28/26 12 PM - 1 PM,
3/29/26 2 PM - 3 PM
Updated 11 Minutes Ago
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42 photos
56 Yale Street Winchester MA 01890
$2,795,000
Beds: 5
Baths: 3.5
Sq Ft: 4,792
Days on Market: 2
Open: 3/27/26 5 PM - 6:30 PM,
3/28/26 12 PM - 1:30 PM,
3/29/26 12 PM - 1:30 PM
Updated 11 Minutes Ago
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26 photos
2 Priscilla Lane Winchester MA 01890
$2,699,000
Beds: 4
Baths: 3.5
Sq Ft: 4,255
Days on Market: 16
Updated 11 Minutes Ago
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35 photos
2 Abby Rd Winchester MA 01890
$2,649,000
Beds: 4
Baths: 4.5
Sq Ft: 5,614
Days on Market: 1
Open: 3/27/26 11 AM - 12 PM,
3/28/26 12:30 PM - 2 PM,
3/29/26 12:30 PM - 2 PM
Updated 11 Minutes Ago
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42 photos
107 Cambridge Street Winchester MA 01890
$2,499,000
Beds: 6
Baths: 4.5
Sq Ft: 5,824
Days on Market: 291
Updated 11 Minutes Ago
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42 photos
10 Viking Rd Winchester MA 01890
$2,499,000
Beds: 4
Baths: 4
Sq Ft: 5,674
Days on Market: 77
Open: 3/28/26 11 AM - 12:30 PM
Updated 11 Minutes Ago
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37 photos
89 Wildwood St Winchester MA 01890
$2,299,000
Beds: 7
Baths: 5.5
Sq Ft: 4,929
Days on Market: 133
Updated 11 Minutes Ago
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34 photos
12 Yale St Winchester MA 01890
$2,299,000
Beds: 4
Baths: 2.5
Sq Ft: 3,283
Days on Market: 29
Updated 11 Minutes Ago
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42 photos
10 Edgehill Road Winchester MA 01890
$2,250,000
Beds: 7
Baths: 3.5
Sq Ft: 3,926
Days on Market: 3
Open: 3/27/26 12 PM - 1:30 PM,
3/28/26 12 PM - 1:30 PM,
3/29/26 12 PM - 1:30 PM
Updated 11 Minutes Ago
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42 photos
61 Grove Street Winchester MA 01890
$2,199,000
Beds: 5
Baths: 4.5
Sq Ft: 4,798
Days on Market: 64
Updated 11 Minutes Ago
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40 photos
6 Ivy Cir Winchester MA 01890
$2,150,000
-$100,000
Beds: 6
Baths: 4
Sq Ft: 3,728
Days on Market: 171
Open: 3/29/26 12 PM - 1:30 PM
Updated 11 Minutes Ago
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42 photos
15 Wildwood Street Winchester MA 01890
$2,100,000
Beds: 6
Baths: 2.5
Sq Ft: 4,104
Days on Market: 9
Updated 11 Minutes Ago
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42 photos
4 Leslie Road Winchester MA 01890
$1,999,900
Beds: 5
Baths: 3.5
Sq Ft: 2,860
Days on Market: 16
Updated 11 Minutes Ago
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35 photos
237 Swanton Street Winchester MA 01890
$1,945,000
-$50,000
Beds: 5
Baths: 4
Sq Ft: 4,334
Days on Market: 113
Open: 3/29/26 1 PM - 2 PM
Updated 11 Minutes Ago
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40 photos
1 Town Way Winchester MA 01890
$1,899,000
Beds: 3
Baths: 3.5
Sq Ft: 3,010
Days on Market: 79
Open: 3/29/26 1:30 PM - 3 PM
Updated 11 Minutes Ago
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Style
- Bungalow
- Cape
- Colonial
- Colonial Revival
- Contemporary
- Craftsman
- Dutch Colonial
- Mid-Century Modern
- Raised Ranch
- Ranch
- Shingle
- Tudor
- Victorian
Subdivision
- Brooks / Parkhurst / Town Forest
- East Hill
- Flats
- Flats neighborhood
- Ginn neighborhood
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Middlesex / downtown
- Near town/ Pine St neighborhood
- Old Village/ West Side
- The Flats
- West side