110 results in search
42 photos
15 Vinson Circle Winchester MA 01890
$18,000,000
Beds: 6
Baths: 6.5
Sq Ft: 10,000
Days on Market: 24
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
38 photos
4 Dartmouth Winchester MA 01890
$4,299,000
Beds: 5
Baths: 5.5
Sq Ft: 6,526
Days on Market: 45
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
42 photos
724 Main St Winchester MA 01890
$4,000,000
Beds:
Baths:
Sq Ft: 7,010
Days on Market: 32
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
40 photos
15 Foxcroft Rd Winchester MA 01890
$3,799,000
Beds: 8
Baths: 5
Sq Ft: 7,081
Days on Market: 4
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
36 photos
11 Viking Road Winchester MA 01890
$3,600,000
Beds: 7
Baths: 7.5
Sq Ft: 7,429
Days on Market: 88
Open: 10/25/26 2 PM - 3 PM
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
42 photos
7 Hutchinson Road Winchester MA 01890
$3,450,000
Beds: 6
Baths: 4.5
Sq Ft: 5,735
Days on Market: 76
Open: 10/25/26 1 PM - 2 PM
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
28 photos
1 Plymouth Rd. Winchester MA 01890
$3,299,000
Beds: 7
Baths: 7.5
Sq Ft: 7,226
Days on Market: 24
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
42 photos
9 Albamont Road Winchester MA 01890
$3,200,000
Beds: 6
Baths: 5.5
Sq Ft: 6,100
Days on Market: 235
Open: 10/25/26 1 PM - 2 PM
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
4 photos
18 Ridge St Winchester MA 01890
$3,200,000
Beds: 5
Baths: 5.5
Sq Ft: 5,295
Days on Market: 76
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
41 photos
30 Willowdale Rd Winchester MA 01890
$3,200,000
Beds: 8
Baths: 6.5
Sq Ft: 5,750
Days on Market: 40
Open: 10/25/26 1 PM - 2:30 PM
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
42 photos
37 Mayflower Road Winchester MA 01890
$3,149,000
Beds: 7
Baths: 7.5
Sq Ft: 8,540
Days on Market: 47
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
10 photos
5 Forest Cir Winchester MA 01890
$2,999,000
Beds: 5
Baths: 4.5
Sq Ft: 4,900
Days on Market: 2
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
41 photos
18 Surrey Road Winchester MA 01890
$2,950,000
Beds: 6
Baths: 4
Sq Ft: 4,752
Days on Market: 6
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
30 photos
14 Nassau Drive Winchester MA 01890
$2,750,000
-$49,000
Beds: 6
Baths: 6
Sq Ft: 6,968
Days on Market: 194
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
32 photos
18 Middlesex St Winchester MA 01890
$2,650,000
Beds: 4
Baths: 4.5
Sq Ft: 5,233
Days on Market: 3
Open: 10/25/26 11:30 AM - 1 PM
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
42 photos
7 Lakeview Terrace Winchester MA 01890
$2,400,000
-$200,000
Beds: 6
Baths: 3
Sq Ft: 3,534
Days on Market: 39
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
42 photos
54 Squire Road Winchester MA 01890
$2,399,000
Beds: 4
Baths: 4.5
Sq Ft: 4,450
Days on Market: 75
Open: 10/25/26 1 PM - 2:30 PM,
10/29/26 4:30 PM - 6:30 PM
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
39 photos
63 Wedgemere Avenue Winchester MA 01890
$2,399,000
Beds: 4
Baths: 3
Sq Ft: 3,550
Days on Market: 19
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
37 photos
9 Plymouth Rd Winchester MA 01890
$2,250,000
Beds: 5
Baths: 3
Sq Ft: 4,071
Days on Market: 111
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
40 photos
19 Hancock Street Winchester MA 01890
$2,199,000
Beds: 4
Baths: 3.5
Sq Ft: 3,570
Days on Market: 47
Open: 10/25/26 11:30 AM - 1 PM
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
41 photos
276 High Street Winchester MA 01890
$2,195,000
Beds: 5
Baths: 3.5
Sq Ft: 5,006
Days on Market: 202
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
36 photos
6 Ivy Circle Winchester MA 01890
$2,100,000
Beds: 6
Baths: 4
Sq Ft: 3,403
Days on Market: 178
Open: 10/25/26 3:30 PM - 4:30 PM
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
42 photos
21 Amberwood Dr Winchester MA 01890
$2,049,000
Beds: 5
Baths: 3.5
Sq Ft: 4,063
Days on Market: 18
Open: 10/25/26 10 AM - 12 PM
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
42 photos
7 Wainwright Road #113 Winchester MA 01890
$1,999,000
Beds: 4
Baths: 3.5
Sq Ft: 3,640
Days on Market: 88
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
42 photos
30 Surrey Rd Winchester MA 01890
$1,985,000
Beds: 4
Baths: 3.5
Sq Ft: 4,241
Days on Market: 11
Open: 10/25/26 1 PM - 2:30 PM
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
38 photos
85 High St Winchester MA 01890
$1,899,000
Beds: 4
Baths: 2.5
Sq Ft: 3,757
Days on Market: 67
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
40 photos
1 Overlook Way Winchester MA 01890
$1,750,000
-$100,000
Beds: 4
Baths: 2.5
Sq Ft: 3,604
Days on Market: 32
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
41 photos
1 Town Way Winchester MA 01890
$1,749,000
Beds: 3
Baths: 3.5
Sq Ft: 3,010
Days on Market: 89
Open: 10/25/26 11:30 AM - 1 PM
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
37 photos
17 Churchill Rd Winchester MA 01890
$1,749,000
Beds: 5
Baths: 3.5
Sq Ft: 3,508
Days on Market: 47
Open: 10/25/26 12 PM - 1 PM
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
42 photos
117 Highland Winchester MA 01890
$1,650,000
Beds: 5
Baths: 3.5
Sq Ft: 3,722
Days on Market: 46
Updated 15 Minutes Ago
Trip MapRequest InfoAppointment
Style
- Antique
- Bungalow
- Cape
- Colonial
- Colonial Revival
- Contemporary
- Craftsman
- Farmhouse
- Garrison
- Greek Revival
- Ranch
- Shingle
- Split Entry
- Tudor
- Victorian
- Villa
Subdivision
- Cox Road / High St Extension neighborhood
- Downtown neighborhood location
- East Hill
- East Side
- Flats
- Lakeview/Ravenscroft
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Middlesex / downtown
- Mystic Lake Area
- West Side
- West Side Ambrose Neighborhood
- West side, on a cul de sac
- Winchester town center