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.
For sale
C$3,400,000
29 Winchester St, Toronto, ON M4X 1A6
4beds
4baths
Quadruplex
Built in ----
-- sqft lot
$-- Zestimate®
C$--/sqft
C$-- HOA
What's special
Multiple walk-out exterior spacesFine interior finishesHardwood floorsUpdated bathroomsUpdated kitchensHigh ceilingsLarge windows
- 55 days
- 40
- 2
Zillow last checked:
Listing updated:
Listed by:
ROYAL LEPAGE TERREQUITY SW REALTY
Source: TRREB,MLS®#: C13578164
Originating MLS®#: Toronto Regional Real Estate Board
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
Bedroom
- Level: Second
- Dimensions: 4.01 x 2.95
Bedroom
- Level: Lower
- Dimensions: 4.11 x 3.05
Bedroom
- Level: Third
- Dimensions: 4.8 x 3.28
Bedroom
- Level: Main
- Dimensions: 4.04 x 4.65
Family room
- Level: Second
- Dimensions: 4.98 x 2.97
Family room
- Level: Main
- Dimensions: 4.98 x 2.97
Family room
- Level: Lower
- Dimensions: 4.98 x 2.97
Kitchen
- Level: Third
- Dimensions: 4.75 x 1.68
Kitchen
- Level: Lower
- Dimensions: 3.96 x 2.13
Kitchen
- Level: Main
- Dimensions: 4.37 x 2.16
Kitchen
- Level: Second
- Dimensions: 2.37 x 2.16
Living room
- Level: Third
- Dimensions: 5.05 x 3.91
Living room
- Level: Second
- Dimensions: 7.09 x 4.65
Living room
- Level: Lower
- Dimensions: 7.04 x 4.7
Living room
- Level: Main
- Dimensions: 7.04 x 4.7
Heating
- Baseboard, Electric
Cooling
- Wall Unit(s)
Features
- None
- Basement: Apartment
- Has fireplace: Yes
Interior area
- Living area range: 3000-3500 null
Video & virtual tour
Property
Parking
- Total spaces: 4
- Parking features: Lane, Private, Assigned
Accessibility
- Accessibility features: None
Features
- Stories: 3
- Pool features: None
Lot
- Size: 4,042 Square Feet
- Features: Library, Park, Place Of Worship, Public Transit, School
Details
- Additional structures: None
- Parcel number: 210870236
Construction
Type & style
- Home type: MultiFamily
- Property subtype: Quadruplex
Materials
- Brick
- Foundation: Unknown
- Roof: Unknown
Utilities & green energy
- Sewer: Sewer
Community & HOA
Community
- Security: None
Location
- Region: Toronto
Financial & listing details
- Annual tax amount: C$12,353
- Date on market: 7/17/2026
Price history
Price history is unavailable.
Public tax history
Tax history is unavailable.
Climate risks
Neighborhood: Cabbagetown
Nearby schools
GreatSchools rating
No schools nearby
We couldn't find any schools near this home.







