81 results in search
36 photos
20 Amberwood Dr Winchester MA 01890
$3,600,000
Beds: 6
Baths: 7
Sq Ft: 8,866
Days on Market: 320
Updated 10 Minutes Ago
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35 photos
1 Plymouth Rd Winchester MA 01890
$3,299,000
Beds: 7
Baths: 7.5
Sq Ft: 7,226
Days on Market: 101
Open: 7/18/26 3 PM - 4 PM,
7/20/26 5:30 PM - 7 PM
Updated 10 Minutes Ago
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10 photos
9 Albamont Road Winchester MA 01890
$3,200,000
Beds: 6
Baths: 5.5
Sq Ft: 6,100
Days on Market: 136
Updated 10 Minutes Ago
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42 photos
10 Rangeley Road Winchester MA 01890
$3,199,000
Beds: 5
Baths: 4.5
Sq Ft: 5,406
Days on Market: 34
Updated 10 Minutes Ago
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40 photos
37 Mayflower Road Winchester MA 01890
$3,179,000
-$200,000
Beds: 7
Baths: 7.5
Sq Ft: 8,540
Days on Market: 93
Open: 7/18/26 1 PM - 2:30 PM
Updated 10 Minutes Ago
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36 photos
8 Priscilla Ln Winchester MA 01890
$3,149,000
Beds: 5
Baths: 5.5
Sq Ft: 6,500
Days on Market: 73
Open: 7/18/26 11 AM - 12 PM
Updated 10 Minutes Ago
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42 photos
10 Dartmouth Street Winchester MA 01890
$2,999,000
Beds: 5
Baths: 3
Sq Ft: 4,028
Days on Market: 8
Open: 7/19/26 11 AM - 12:30 PM
Updated 10 Minutes Ago
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30 photos
14 Nassau Drive Winchester MA 01890
$2,799,000
Beds: 6
Baths: 6
Sq Ft: 6,968
Days on Market: 95
Updated 10 Minutes Ago
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32 photos
18 Middlesex St Winchester MA 01890
$2,795,000
Beds: 4
Baths: 4.5
Sq Ft: 5,233
Days on Market: 66
Open: 7/18/26 11 AM - 12:30 PM
Updated 10 Minutes Ago
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37 photos
9 Plymouth Rd Winchester MA 01890
$2,500,000
Beds: 5
Baths: 3
Sq Ft: 4,071
Days on Market: 12
Updated 10 Minutes Ago
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42 photos
78 Bacon Street Winchester MA 01890
$2,499,000
-$30,000
Beds: 5
Baths: 3.5
Sq Ft: 5,230
Days on Market: 51
Open: 7/18/26 11 AM - 12:30 PM
Updated 10 Minutes Ago
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16 photos
53 Winford Way Winchester MA 01890
$2,399,000
Beds: 5
Baths: 4
Sq Ft: 5,083
Days on Market: 52
Open: 7/18/26 11 AM - 12 PM,
7/19/26 11 AM - 12 PM
Updated 10 Minutes Ago
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40 photos
14 Hillside Ave Winchester MA 01890
$2,380,000
Beds: 4
Baths: 4.5
Sq Ft: 3,881
Days on Market: 24
Open: 7/19/26 12 PM - 1:30 PM
Updated 10 Minutes Ago
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38 photos
276 High Street Winchester MA 01890
$2,195,000
Beds: 5
Baths: 3.5
Sq Ft: 5,006
Days on Market: 103
Open: 7/18/26 11:30 AM - 12:30 PM
Updated 10 Minutes Ago
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36 photos
26 N Gateway Winchester MA 01890
$2,149,000
-$50,000
Beds: 4
Baths: 3.5
Sq Ft: 3,210
Days on Market: 30
Open: 7/18/26 11 AM - 12 PM,
7/19/26 11 AM - 12 PM
Updated 10 Minutes Ago
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42 photos
15 Fieldstone Dr Winchester MA 01890
$1,975,000
-$24,900
Beds: 4
Baths: 3.5
Sq Ft: 3,286
Days on Market: 31
Open: 7/19/26 11:30 AM - 1 PM
Updated 10 Minutes Ago
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41 photos
16 & 16A Glenwood Ave Winchester MA 01890
$1,899,000
-$100,000
Beds: 6
Baths: 4.5
Sq Ft: 6,900
Days on Market: 85
Open: 7/18/26 12:30 PM - 1:30 PM
Updated 10 Minutes Ago
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41 photos
16 Glenwood Ave Winchester MA 01890
$1,899,000
-$100,000
Beds: 6
Baths: 4.5
Sq Ft: 6,900
Days on Market: 85
Open: 7/18/26 12:30 PM - 1:30 PM
Updated 10 Minutes Ago
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41 photos
79 Grove St Winchester MA 01890
$1,899,000
Beds: 5
Baths: 3.5
Sq Ft: 3,210
Days on Market: 11
Open: 7/18/26 12 PM - 1:30 PM,
7/19/26 12 PM - 1:30 PM
Updated 10 Minutes Ago
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27 photos
8 Hawthorne Road Winchester MA 01890
$1,825,000
-$25,000
Beds: 5
Baths: 3
Sq Ft: 3,315
Days on Market: 57
Updated 10 Minutes Ago
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42 photos
18 Graystone Circle #18 Winchester MA 01890
$1,750,000
Beds: 3
Baths: 2.5
Sq Ft: 2,833
Days on Market: 2
Updated 10 Minutes Ago
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40 photos
117 Highland Ave Winchester MA 01890
$1,725,000
Beds: 5
Baths: 3.5
Sq Ft: 3,722
Days on Market: 30
Open: 7/19/26 12 PM - 1:30 PM
Updated 10 Minutes Ago
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42 photos
2 Olde Lyme Road Winchester MA 01890
$1,699,000
Beds: 3
Baths: 3.5
Sq Ft: 2,513
Days on Market: 5
Open: 7/18/26 11 AM - 12:30 PM,
7/19/26 11 AM - 12:30 PM
Updated 10 Minutes Ago
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39 photos
241 Ridge St Winchester MA 01890
$1,599,000
Beds: 4
Baths: 3
Sq Ft: 2,480
Days on Market: 10
Updated 10 Minutes Ago
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42 photos
423 Washington St Winchester MA 01890
$1,350,000
Beds: 4
Baths: 3
Sq Ft: 2,690
Days on Market: 23
Open: 7/19/26 2 PM - 3 PM
Updated 10 Minutes Ago
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32 photos
7 Wainwright Road #47 Winchester MA 01890
$1,299,000
-$31,000
Beds: 3
Baths: 3
Sq Ft: 2,145
Days on Market: 37
Open: 7/19/26 12:30 PM - 2 PM
Updated 10 Minutes Ago
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36 photos
53 Lake Street Winchester MA 01890
$1,199,000
Beds: 3
Baths: 2.5
Sq Ft: 2,235
Days on Market: 65
Open: 7/18/26 1 PM - 2 PM
Updated 10 Minutes Ago
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41 photos
52 Middlesex Street #52 Winchester MA 01890
$1,195,000
Beds: 4
Baths: 2.5
Sq Ft: 2,303
Days on Market: 11
Updated 10 Minutes Ago
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32 photos
38 Robinhood Rd Winchester MA 01890
$1,175,000
-$50,000
Beds: 3
Baths: 2
Sq Ft: 1,736
Days on Market: 31
Open: 7/19/26 1 PM - 2:30 PM
Updated 10 Minutes Ago
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33 photos
955 Main St #305 Winchester MA 01890
$1,150,000
Beds:
Baths:
Sq Ft: 2,054
Days on Market: 82
Updated 10 Minutes Ago
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Style
- Bungalow
- Cape
- Colonial
- Colonial Revival
- Contemporary
- Craftsman
- Dutch Colonial
- Farmhouse
- Italianate
- Other (See Remarks)
- Raised Ranch
- Ranch
- Victorian
- Villa
Subdivision
- Cox Road / High St Extension neighborhood
- Flats
- Flats area
- Flats neighborhood
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Middlesex / downtown
- Rangeley Estate Park
- Rangeley Estates
- Vinson-Owen School District.
- West Side