104 results in search
41 photos
2 Everett Ave Winchester MA 01890
$4,174,000
Beds: 7
Baths: 4.5
Sq Ft: 7,043
Days on Market: 88

Updated 8 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: 175

Updated 8 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: 95
Open: 12/7/25 12 PM - 1:30 PM

Updated 8 Minutes Ago
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42 photos
257 High Street Winchester MA 01890
$3,299,000
Beds: 5
Baths: 6
Sq Ft: 7,101
Days on Market: 92

Updated 8 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: 56

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39 photos
44 Cabot Street Winchester MA 01890
$3,099,000
Beds: 6
Baths: 6.5
Sq Ft: 6,028
Days on Market: 70
Open: 12/7/25 12 PM - 1 PM

Updated 8 Minutes Ago
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42 photos
19 Town Way Winchester MA 01890
$2,999,000
Beds: 5
Baths: 5.5
Sq Ft: 5,257
Days on Market: 17
Open: 12/7/25 11:30 AM - 1 PM

Updated 8 Minutes Ago
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30 photos
14 Nassau Drive Winchester MA 01890
$2,850,000
Beds: 6
Baths: 6
Sq Ft: 6,968
Days on Market: 72

Updated 8 Minutes Ago
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41 photos
10 Sheffield Road Winchester MA 01890
$2,799,000
Beds: 7
Baths: 5.5
Sq Ft: 5,864
Days on Market: 186

Updated 8 Minutes Ago
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41 photos
10 Viking Rd Winchester MA 01890
$2,600,000
-$95,000
Beds: 4
Baths: 4
Sq Ft: 5,674
Days on Market: 36
Open: 12/7/25 1 PM - 2:30 PM

Updated 8 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: 179

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42 photos
9 Norfolk Rd Winchester MA 01890
$2,399,000
Beds: 6
Baths: 3.5
Sq Ft: 4,320
Days on Market: 23

Updated 8 Minutes Ago
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40 photos
29 Shepard Ct Winchester MA 01890
$2,399,000
Beds: 6
Baths: 5
Sq Ft: 4,594
Days on Market: 16

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40 photos
14 Grant Rd Winchester MA 01890
$2,349,000
Beds: 6
Baths: 4.5
Sq Ft: 4,200
Days on Market: 64

Updated 8 Minutes Ago
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38 photos
276 High Street Winchester MA 01890
$2,299,000
Beds: 5
Baths: 3.5
Sq Ft: 5,006
Days on Market: 144

Updated 8 Minutes Ago
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42 photos
19 Gershon Way #1 Winchester MA 01890
$2,299,000
Beds: 3
Baths: 2.5
Sq Ft: 3,953
Days on Market: 28

Updated 8 Minutes Ago
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42 photos
19 Gershon Way Winchester MA 01890
$2,299,000
Beds: 3
Baths: 2.5
Sq Ft: 3,953
Days on Market: 28

Updated 8 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: 21
Open: 12/6/25 11 AM - 12 PM,
12/7/25 12:45 PM - 2 PM

Updated 8 Minutes Ago
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42 photos
7-7A Brooks St Winchester MA 01890
$2,275,000
Beds: 6
Baths: 3.5
Sq Ft: 4,122
Days on Market: 16
Open: 12/7/25 12 PM - 1:30 PM

Updated 8 Minutes Ago
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42 photos
7-7A Brooks St Winchester MA 01890
$2,275,000
Beds: 6
Baths: 3.5
Sq Ft: 4,122
Days on Market: 14
Open: 12/7/25 12 PM - 1:30 PM

Updated 8 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: 59
Open: 12/7/25 12 PM - 1:30 PM

Updated 8 Minutes Ago
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42 photos
5 Bacon St Winchester MA 01890
$2,190,000
Beds: 6
Baths: 4
Sq Ft: 4,385
Days on Market: 127

Updated 8 Minutes Ago
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42 photos
5 Bacon St Winchester MA 01890
$2,190,000
Beds: 6
Baths: 4
Sq Ft: 4,385
Days on Market: 127

Updated 8 Minutes Ago
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42 photos
30 Prospect St Winchester MA 01890
$2,099,000
Beds: 4
Baths: 3
Sq Ft: 2,519
Days on Market: 20

Updated 8 Minutes Ago
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42 photos
5 Azalea Road Winchester MA 01890
$1,999,000
Beds: 5
Baths: 3.5
Sq Ft: 6,232
Days on Market: 56

Updated 8 Minutes Ago
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31 photos
46 Church St Winchester MA 01890
$1,999,000
Beds: 4
Baths: 3.5
Sq Ft: 3,475
Days on Market: 4
Open: 12/6/25 12 PM - 1:30 PM,
12/7/25 12:30 PM - 2 PM

Updated 8 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: 1
Open: 12/7/25 11 AM - 12:30 PM

Updated 8 Minutes Ago
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42 photos
8 Felsdale Close Winchester MA 01890
$1,990,000
-$85,000
Beds: 4
Baths: 2.5
Sq Ft: 3,658
Days on Market: 28
Open: 12/7/25 11 AM - 12:30 PM

Updated 8 Minutes Ago
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42 photos
19 Glengarry Road Winchester MA 01890
$1,975,000
Beds: 6
Baths: 3.5
Sq Ft: 3,521
Days on Market: 113

Updated 8 Minutes Ago
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42 photos
5 Wood Lane Winchester MA 01890
$1,950,000
Beds: 3
Baths: 2.5
Sq Ft: 2,443
Days on Market: 36

Updated 8 Minutes Ago
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