69 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: 43
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
41 photos
2 Everett Ave Winchester MA 01890
$3,747,000
Beds: 7
Baths: 4.5
Sq Ft: 7,043
Days on Market: 29
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
41 photos
40 Foxcroft Rd Winchester MA 01890
$3,650,000
Beds: 6
Baths: 4.5
Sq Ft: 6,460
Days on Market: 36
Open: 4/18/26 11 AM - 12:30 PM
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
36 photos
20 Amberwood Dr Winchester MA 01890
$3,600,000
Beds: 6
Baths: 7
Sq Ft: 8,866
Days on Market: 228
Open: 4/18/26 1:30 PM - 2:30 PM
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
42 photos
54 Johnson Rd Winchester MA 01890
$3,499,000
Beds: 5
Baths: 7.5
Sq Ft: 6,899
Days on Market: 72
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
10 photos
9 Albamont Road Winchester MA 01890
$3,400,000
Beds: 6
Baths: 5.5
Sq Ft: 6,100
Days on Market: 44
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
35 photos
1 Plymouth Rd Winchester MA 01890
$3,399,000
Beds: 7
Baths: 7.5
Sq Ft: 7,226
Days on Market: 9
Open: 4/19/26 12 PM - 1:30 PM
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
31 photos
25 Myopia Road Winchester MA 01890
$3,390,000
Beds: 4
Baths: 3.5
Sq Ft: 4,847
Days on Market: 81
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
39 photos
37 Mayflower Road Winchester MA 01890
$3,379,000
Beds: 7
Baths: 7.5
Sq Ft: 8,540
Days on Market: 1
Open: 4/19/26 11 AM - 12:30 PM
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
42 photos
74 Wedgemere Avenue Winchester MA 01890
$3,299,000
Beds: 5
Baths: 4.5
Sq Ft: 5,202
Days on Market: 8
Open: 4/18/26 11 AM - 12:30 PM
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
39 photos
27 Everett Ave Winchester MA 01890
$3,290,000
Beds: 6
Baths: 5.5
Sq Ft: 7,431
Days on Market: 92
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
40 photos
257 High Street Winchester MA 01890
$3,250,000
Beds: 5
Baths: 6
Sq Ft: 7,101
Days on Market: 8
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
42 photos
12 Salisbury Street Winchester MA 01890
$3,200,000
Beds: 6
Baths: 4.5
Sq Ft: 5,107
Days on Market: 11
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
42 photos
10 Dartmouth Street Winchester MA 01890
$2,999,000
Beds: 5
Baths: 3
Sq Ft: 4,028
Days on Market: 11
Open: 4/18/26 11 AM - 12:30 PM
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
36 photos
14 Nassau Drive Winchester MA 01890
$2,850,000
Beds: 6
Baths: 6
Sq Ft: 6,968
Days on Market: 3
Open: 4/18/26 1:15 PM - 2:45 PM,
4/19/26 1:15 PM - 2:45 PM
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
32 photos
2 Edgewater Place Winchester MA 01890
$2,800,000
Beds: 4
Baths: 4.5
Sq Ft: 3,945
Days on Market: 8
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
16 photos
53 Winford Way Winchester MA 01890
$2,799,000
Beds: 5
Baths: 4
Sq Ft: 5,083
Days on Market: 46
Open: 4/18/26 12 PM - 1 PM,
4/19/26 12 PM - 1 PM
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
35 photos
15 Gershon Way #15 Winchester MA 01890
$2,395,000
Beds: 3
Baths: 3.5
Sq Ft: 4,087
Days on Market: 15
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
35 photos
15 Gershon Way #15 Winchester MA 01890
$2,395,000
Beds: 3
Baths: 3.5
Sq Ft: 4,087
Days on Market: 15
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
38 photos
276 High Street Winchester MA 01890
$2,299,000
Beds: 5
Baths: 3.5
Sq Ft: 5,006
Days on Market: 11
Open: 4/18/26 11 AM - 12:30 PM
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
34 photos
15 Cabot St Winchester MA 01890
$2,149,000
Beds: 4
Baths: 2.5
Sq Ft: 3,123
Days on Market: 1
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
34 photos
237 Swanton Street Winchester MA 01890
$1,995,000
Beds: 5
Baths: 4
Sq Ft: 4,334
Days on Market: 11
Open: 4/18/26 11 AM - 12:30 PM
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
37 photos
94 Johnson Road Winchester MA 01890
$1,899,999
Beds: 4
Baths: 3
Sq Ft: 3,512
Days on Market: 9
Open: 4/18/26 11 AM - 12:30 PM
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
33 photos
2 Gershon Way #2 Winchester MA 01890
$1,899,000
Beds: 3
Baths: 2.5
Sq Ft: 2,306
Days on Market: 10
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
34 photos
2 Gershon Way Winchester MA 01890
$1,899,000
Beds: 3
Baths: 2.5
Sq Ft: 2,306
Days on Market: 10
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
40 photos
1 Town Way Winchester MA 01890
$1,874,000
-$25,000
Beds: 3
Baths: 3.5
Sq Ft: 3,010
Days on Market: 100
Open: 4/19/26 12 PM - 1:30 PM
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
42 photos
29 Pilgrim Dr Winchester MA 01890
$1,749,000
Beds: 5
Baths: 3
Sq Ft: 3,271
Days on Market: 23
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
37 photos
34 Robinhood Road Winchester MA 01890
$1,524,000
Beds: 4
Baths: 2.5
Sq Ft: 3,380
Days on Market: 33
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
23 photos
65 High Street Winchester MA 01890
$1,399,800
Beds: 6
Baths: 3
Sq Ft: 2,658
Days on Market: 8
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
40 photos
7 Wainwright Road #107 Winchester MA 01890
$1,350,000
Beds: 3
Baths: 2.5
Sq Ft: 2,907
Days on Market: 4
Open: 4/18/26 1 PM - 2:30 PM,
4/19/26 1 PM - 2:30 PM
Updated 0 Minutes Ago
Trip MapRequest InfoAppointment
Style
- Bungalow
- Cape
- Colonial
- Colonial Revival
- Contemporary
- Cottage
- Craftsman
- Mid-Century Modern
- Raised Ranch
- Ranch
- Shingle
- Tudor
- Victorian
Subdivision
- Brooks / Parkhurst / Town Forest
- Cox Road / High St Extension neighborhood
- East Hill
- Flats
- Flats neighborhood
- Ginn neighborhood
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Macdonald field neighborhood
- Middlesex / downtown
- Near town/ Pine St neighborhood
- Old Village/ West Side
- The Flats
- West Side
- Winning Farm