29 Winchester Street, Toronto

29 Winchester Street
29 Winchester Street
29 Winchester Street
+47
3+1
 bed
4
 bath
4
 parking
3000 - 3500
 sqft
Fourplex
$3,400,000
For Sale
8 days
 on site
$3,400,000
Click to open the pre-gallery to get the direction
Size
-
Lot size
4042 sqft
Street frontage
-
Possession
Flexible
Price per sqft
$971 - $1,133
Taxes
$12,353.71 (2026)
Parking Type
-
Style
3-Storey
See what's nearby
Description
The finest 4-plex in Cabbagetown has returned to market for the first time in a generation! This impeccably maintained and professionally updated income property has been meticulously renovated and represents a rare opportunity to acquire a best-in-class asset of this stature in one of Toronto's most storied neighbourhoods. Over 4200+ sq ft of living space, complimented with multiple walk-out exterior spaces including 2x large private decks, a rear walk-out patio at grade, and a stunning oversized south facing rooftop terrace on the upper level overlooking lush rear grounds under a densely treed canopy. The building is home to a high-quality tenant base, and each suite enjoys dedicated climate controls. The building has been curated to appeal to professionals and offers living spaces that are ideal for both entertaining and relaxing in a quiet environment. Fine interior finishes include hardwood floors, updated bathrooms, updated kitchens, high ceilings, and large windows. Each unit has dedicated ensuite laundry. Parking is accessed via a private rear laneway off of Aberdeen Ave, including 4 parking spaces at present (of which 1 is a tandem parking space,) and the possibility exists to expand up to 6 car parking on site). 29 Winchester has been assembled to remain highly desireable and strongly appealing to tenants in any market. This premium location is steps to restos and shopping along Parliament Street, and accessible to multiple TTC options (including the Carlton Street Car) or a short walk to Castle Frank Station TTC Subway. Tenants can enjoy Winchester Park at their doorstep, or stroll to Riverdale farm. Mere minutes to the downtown core and Distillery District / St Lawrence Market. Shows 10+ and must be seen - a perfect addition for any investor seeking a high calibre investment grade property to add to their portfolio.
Broker: ROYAL LEPAGE TERREQUITY SW REALTY
MLS®#: C13578164
Property details
Parking:
4
Parking type:
-
Property type:
Fourplex
Heating type:
Baseboard
Style:
3-Storey
MLS Size:
3000-3500 sqft
Lot front:
28 Ft
Lot depth:
142 Ft
Listed on:
Jul 17, 2026
Show all details
Rooms
LevelNameSizeFeatures
Third
Kitchen
15.6 x 5.5 ft
Second
Bedroom
13.2 x 9.7 ft
Third
Living Room
16.6 x 12.8 ft
Show all
Instant estimate:
orto view instant estimate
$295,433
lower than listed price
i
High
$3,215,284
Mid
$3,104,567
Low
$2,948,356
Have a home? See what it's worth with an instant estimate

Use our AI-assisted tool to get an instant estimate of your home's value, up-to-date neighbourhood sales data, and tips on how to sell for more.

76 Poplar Plains Crescent
1/3
$3,300,000
67 days
76 Poplar Plains Crescent
4+2BD
5BA
2 Parking
3,000-3,500 sqft
MLS#: C13143828
ROYAL LEPAGE/J & D DIVISION
67 days
452 Montrose Avenue
1/40
$3,299,000
11 days
452 Montrose Avenue
5+1BD
5BA
0 Parking
3,000-3,500 sqft
MLS#: C13562684
EXP REALTY
11 days
309 Lonsdale Road
1/36
$2,999,000
7 days
309 Lonsdale Road
3+1BD
4BA
3 Parking
3,000-3,500 sqft
MLS#: C13580724
FOREST HILL REAL ESTATE INC.
7 days
44 Foxley Street
1/40
$3,195,000
44 days
44 Foxley Street
5+2BD
8BA
1 Parking
3,000-3,500 sqft
MLS#: C13430594
ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM
44 days

About 29 Winchester Street

Located at 29 Winchester Street, this Toronto fourplex is available for sale. It was listed at $3400000 in July 2026 and has 3+1 beds and 4 bathrooms. 29 Winchester Street resides in the Toronto Cabbagetown neighbourhood, and nearby areas include St. James Town, Church St. Corridor, Regent Park and Moss Park.

There are a lot of great restaurants around 29 Winchester St, Toronto. If you can't start your day without caffeine fear not, your nearby choices include Tim Hortons. For grabbing your groceries, Fairway Variety is only steps away.

Living in this Cabbagetown fourplex is easy. There is also Parliament St at Winchester St Bus Stop, only steps away, with route Parliament, and route Parliament Night Bus nearby. Access to Don Valley Parkway from 29 Winchester St is within a 4-minute drive, making it easy for those driving to get into and out of the city