110 results in search
38 photos
4 Dartmouth Winchester MA 01890
$4,299,000
Beds: 5
Baths: 5.5
Sq Ft: 6,526
Days on Market: 20
Updated 1 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: 7
Updated 1 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: 63
Updated 1 Minutes Ago
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42 photos
7 Hutchinson Road Winchester MA 01890
$3,450,000
Beds: 6
Baths: 4.5
Sq Ft: 5,735
Days on Market: 51
Updated 1 Minutes Ago
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42 photos
9 Albamont Road Winchester MA 01890
$3,200,000
Beds: 6
Baths: 5.5
Sq Ft: 6,100
Days on Market: 210
Updated 1 Minutes Ago
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4 photos
18 Ridge St Winchester MA 01890
$3,200,000
Beds: 5
Baths: 5.5
Sq Ft: 5,295
Days on Market: 51
Updated 1 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: 15
Updated 1 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: 22
Updated 1 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: 169
Updated 1 Minutes Ago
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32 photos
18 Middlesex St Winchester MA 01890
$2,695,000
Beds: 4
Baths: 4.5
Sq Ft: 5,233
Days on Market: 140
Updated 1 Minutes Ago
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42 photos
7 Lakeview Terrace Winchester MA 01890
$2,600,000
Beds: 6
Baths: 3
Sq Ft: 3,534
Days on Market: 14
Updated 1 Minutes Ago
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42 photos
54 Squire Road Winchester MA 01890
$2,450,000
Beds: 4
Baths: 4.5
Sq Ft: 4,450
Days on Market: 50
Updated 1 Minutes Ago
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37 photos
9 Plymouth Rd Winchester MA 01890
$2,250,000
-$150,000
Beds: 5
Baths: 3
Sq Ft: 4,071
Days on Market: 86
Updated 1 Minutes Ago
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40 photos
19 Hancock Street Winchester MA 01890
$2,199,000
Beds: 4
Baths: 3.5
Sq Ft: 3,570
Days on Market: 22
Open: 10/4/26 11:30 AM - 1 PM
Updated 1 Minutes Ago
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36 photos
276 High Street Winchester MA 01890
$2,195,000
Beds: 5
Baths: 3.5
Sq Ft: 5,006
Days on Market: 177
Updated 1 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: 153
Updated 1 Minutes Ago
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42 photos
7 Wainwright Road #113 Winchester MA 01890
$2,100,000
Beds: 4
Baths: 3.5
Sq Ft: 3,640
Days on Market: 63
Updated 1 Minutes Ago
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38 photos
85 High St Winchester MA 01890
$1,999,000
Beds: 4
Baths: 2.5
Sq Ft: 3,757
Days on Market: 42
Updated 1 Minutes Ago
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42 photos
26 Mayflower Road Winchester MA 01890
$1,950,000
Beds: 5
Baths: 4
Sq Ft: 3,371
Days on Market: 1
Open: 10/1/26 4:30 PM - 6 PM,
10/3/26 11 AM - 12:30 PM,
10/4/26 11 AM - 12:30 PM
Updated 1 Minutes Ago
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42 photos
79 Grove St Winchester MA 01890
$1,870,000
-$29,000
Beds: 5
Baths: 3.5
Sq Ft: 3,210
Days on Market: 85
Open: 10/2/26 12 PM - 1:30 PM,
10/3/26 12 PM - 1:30 PM
Updated 1 Minutes Ago
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40 photos
1 Overlook Way Winchester MA 01890
$1,850,000
Beds: 4
Baths: 2.5
Sq Ft: 3,092
Days on Market: 7
Open: 10/2/26 12 PM - 1:30 PM,
10/3/26 12 PM - 1:30 PM,
10/4/26 12 PM - 1:30 PM
Updated 1 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: 22
Updated 1 Minutes Ago
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42 photos
4 Churchill Road Winchester MA 01890
$1,699,000
Beds: 3
Baths: 2
Sq Ft: 2,421
Days on Market: 23
Updated 1 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: 21
Updated 1 Minutes Ago
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42 photos
143 Arlington Street Winchester MA 01890
$1,599,000
Beds: 5
Baths: 2
Sq Ft: 2,944
Days on Market: 20
Updated 1 Minutes Ago
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42 photos
50 Holland Street Winchester MA 01890
$1,549,000
Beds: 3
Baths: 2.5
Sq Ft: 2,640
Days on Market: 63
Updated 1 Minutes Ago
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42 photos
7 Sherman Place #7 Winchester MA 01890
$1,495,000
Beds: 4
Baths: 2.5
Sq Ft: 2,973
Days on Market: 15
Updated 1 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: 97
Updated 1 Minutes Ago
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31 photos
9 Priscilla Ln Winchester MA 01890
$1,325,000
Beds: 4
Baths: 2
Sq Ft: 1,922
Days on Market: 12
Updated 1 Minutes Ago
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28 photos
465 Washington Street Winchester MA 01890
$1,300,000
Beds: 4
Baths: 2.5
Sq Ft: 2,666
Days on Market: 20
Updated 1 Minutes Ago
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Style
- Antique
- Bungalow
- Cape
- Colonial
- Colonial Revival
- Contemporary
- Craftsman
- Farmhouse
- Garrison
- Greek Revival
- Ranch
- Split Entry
- Tudor
- Victorian
- Villa
Subdivision
- Cox Road / High St Extension neighborhood
- East Hill
- East Side
- Flats
- Lakeview/Ravenscroft
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Middlesex / downtown
- Near leonard field
- Rangeley Estate Park
- West Side
- West Side Ambrose Neighborhood
- West side, on a cul de sac