81 results in search
42 photos
9 Lakeview Terrace Winchester MA 01890
$3,750,000
Beds: 6
Baths: 3.5
Sq Ft: 4,484
Days on Market: 259
Updated 0 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: 179
Updated 0 Minutes Ago
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39 photos
27 Everett Ave Winchester MA 01890
$3,599,000
Beds: 6
Baths: 5.5
Sq Ft: 7,431
Days on Market: 43
Updated 0 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: 18
Open: 2/28/26 1 PM - 2 PM
Updated 0 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: 23
Updated 0 Minutes Ago
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42 photos
10 Sheffield West Winchester MA 01890
$3,470,000
Beds: 5
Baths: 5
Sq Ft: 6,127
Days on Market: 30
Updated 0 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: 23
Open: 2/28/26 12 PM - 1:30 PM
Updated 0 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: 32
Open: 2/27/26 12 PM - 1 PM,
2/28/26 1:45 PM - 3:30 PM
Updated 0 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: 140
Updated 0 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: 2
Open: 2/27/26 12 PM - 1 PM,
2/28/26 12 PM - 1:30 PM,
3/1/26 1 PM - 2:30 PM
Updated 0 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: 101
Open: 3/1/26 11:30 AM - 1 PM
Updated 0 Minutes Ago
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42 photos
10 Viking Rd Winchester MA 01890
$2,549,000
-$46,000
Beds: 4
Baths: 4
Sq Ft: 5,674
Days on Market: 49
Open: 2/28/26 1:30 PM - 3 PM
Updated 0 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: 263
Updated 0 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: 105
Updated 0 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: 1
Open: 2/27/26 11 AM - 12 PM,
2/28/26 1 PM - 2:30 PM,
3/1/26 1 PM - 2:30 PM
Updated 0 Minutes Ago
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40 photos
6 Ivy Cir Winchester MA 01890
$2,250,000
Beds: 6
Baths: 4
Sq Ft: 3,728
Days on Market: 143
Open: 3/1/26 1 PM - 2:30 PM
Updated 0 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: 36
Open: 2/28/26 12 PM - 2 PM,
3/1/26 12 PM - 2 PM
Updated 0 Minutes Ago
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34 photos
10 Hawthorne Rd Winchester MA 01890
$1,998,000
Beds: 5
Baths: 4.5
Sq Ft: 3,191
Days on Market: 24
Updated 0 Minutes Ago
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35 photos
237 Swanton Street Winchester MA 01890
$1,995,000
Beds: 5
Baths: 4
Sq Ft: 4,334
Days on Market: 85
Open: 2/28/26 11 AM - 12 PM,
3/1/26 12 PM - 1 PM
Updated 0 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: 51
Open: 3/1/26 1:30 PM - 3 PM
Updated 0 Minutes Ago
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42 photos
5 Squire Rd Winchester MA 01890
$1,899,000
Beds: 6
Baths: 3.5
Sq Ft: 4,696
Days on Market: 31
Updated 0 Minutes Ago
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40 photos
20 Grove Pl Winchester MA 01890
$1,869,000
Beds: 5
Baths: 3.5
Sq Ft: 3,294
Days on Market: 102
Updated 0 Minutes Ago
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42 photos
114 Johnson Rd Winchester MA 01890
$1,795,000
Beds: 3
Baths: 3
Sq Ft: 3,182
Days on Market: 8
Open: 2/28/26 2 PM - 4 PM,
3/1/26 2 PM - 4 PM
Updated 0 Minutes Ago
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42 photos
263 Highland Ave Winchester MA 01890
$1,599,000
-$50,000
Beds: 4
Baths: 3
Sq Ft: 3,343
Days on Market: 79
Open: 2/28/26 12 PM - 1:30 PM
Updated 0 Minutes Ago
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39 photos
17 Cranston Rd Winchester MA 01890
$1,560,000
Beds: 4
Baths: 2.5
Sq Ft: 2,578
Days on Market: 2
Open: 2/27/26 4:30 PM - 6 PM,
2/28/26 11 AM - 12:30 PM,
3/1/26 11 AM - 12:30 PM
Updated 0 Minutes Ago
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40 photos
19 Cox Road Winchester MA 01890
$1,499,000
Beds: 3
Baths: 1.5
Sq Ft: 2,351
Days on Market: 310
Updated 0 Minutes Ago
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41 photos
26 Berkshire Dr Winchester MA 01890
$1,460,000
Beds: 3
Baths: 2.5
Sq Ft: 2,316
Days on Market: 115
Updated 0 Minutes Ago
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29 photos
15 Englewood Road Winchester MA 01890
$1,399,900
Beds: 4
Baths: 3
Sq Ft: 1,903
Days on Market: 1
Open: 2/27/26 11 AM - 12 PM,
2/28/26 12 PM - 1:30 PM,
3/1/26 12 PM - 1:30 PM
Updated 0 Minutes Ago
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42 photos
95 Irving Street #95 Winchester MA 01890
$1,399,000
Beds: 4
Baths: 3.5
Sq Ft: 2,490
Days on Market: 87
Updated 0 Minutes Ago
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42 photos
95 Irving Street #95 Winchester MA 01890
$1,399,000
Beds: 4
Baths: 3.5
Sq Ft: 2,490
Days on Market: 87
Updated 0 Minutes Ago
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Style
- Bungalow
- Cape
- Colonial
- Colonial Revival
- Contemporary
- Craftsman
- Dutch Colonial
- Other (See Remarks)
- Raised Ranch
- Ranch
- Shingle
- Split Entry
- Tudor
- Victorian
Subdivision
- East Hill
- Ginn neighborhood
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Near VO school
- Old Village/ West Side
- The Flats
- West side