29 Winchester Street, Toronto, ON M4X 1A6, Toronto C08, ON
Bed 4
Bath 4
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.
Property Highlights
For Sale
MLS NO.
C13578164
Type
Residential Freehold
Sub Type
Fourplex
Bedrooms
4
Bathrooms
4
Parking
4.0
Complete Property Details
Property Type
Residential Freehold
Sub Type
Fourplex
Transaction Type
For Sale
Status
Active
Contract Status
Available
MLS® Number
C13578164
Living Area Range
3000-3500
Total Bedrooms
4
Bedrooms Above Grade
3
Bedrooms Below Grade
1
Total Bathrooms
4
Total Kitchens
4
Kitchens Above Grade
3
Kitchens Below Grade
1
Rooms Above Grade
15
Interior Features
None
Fireplace
Yes
Central Vacuum Yn
No
Security Features
None
Construction
Brick
Roof
Unknown
Lot Width
28.47
Parking Features
Lane, Private, Reserved/Assigned
Parking Total
4.0
Covered Spaces
0.0
Garage Type
None
Garage
No
Pool
None
Direction Facing
South
Cooling
Wall Unit(s)
Heat Source
Electric
Heat Type
Baseboard
Internet Address Display Yn
Yes
Internet Entire Listing Display Yn
Yes
Full Address
29 Winchester Street, Toronto, ON M4X 1A6
City
Toronto C08
Neighbourhood
Cabbagetown-South St. James Town
County / Region
Toronto
Province / State
ON
Postal Code
M4X 1A6
Cross Street
Winchester & Parliament
Directions
Winchester & Parliament
Country
CA
List Price
$3,400,000
Annual Taxes
$12,354
Tax Year
2026
Legal Description
PT LT 8 S/S WINCHESTER ST PL 31 TORONTO PT 1, 63R2053; T/W CT506557 (FIRSTLY DESCRIBED); CITY OF TORONTO
Possession Type
Flexible
Possession Details
TBD
Listing Office
ROYAL LEPAGE TERREQUITY SW REALTY
Board
Toronto Regional Real Estate Board
Original Entry
2026-07-17T18:23:43Z
Media Updated
2026-07-17T18:23:43Z
Photos Updated
2026-07-17T18:23:43Z
Last Modified
2026-07-20T16:26:30Z
System Modified
2026-07-27T22:12:51.660572Z
MLS Status
New
Architectural Style
3-Storey
Basement
Apartment
Co List Office Name
ROYAL LEPAGE TERREQUITY SW REALTY
Ddfyn
Yes
Expiration Date
2026-12-31
Foundation Details
Unknown
Heat Source Multi
Electric, Gas
Heat Type Multi
Baseboard, Forced Air
Hstapplication
Not Subject to HST
Occupant Type
Tenant
Originating System Id
A00001796
Parcel Number
210870236
Parking Spaces
4
Property Features
Library, Park, Place Of Worship, Public Transit, School
Public Remarks
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.
