29 Winchester St
Toronto, ON M4X 1A6
For more information on this listing, contact us at: (647) 360-2908
Active
$3,400,000
29 Winchester St Toronto, ON M4X 1A6
Fourplex
Property Type
4
Beds
4
Baths
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.
MLS #
C13578164
Monthly Assoc. Fee
N/A
On Site
78 Days
Last Updated
9/18/2026
Location
Contact Agent
Ariez Reyes
(647) 360-2908Property Details
Community Information
Address
29 Winchester St, Toronto, ON M4X 1A6
Area
Toronto
City
Toronto
Community
Cabbagetown-South St. James Town
Postal Code
M4X 1A6
Municipality
Toronto C08
Architecture
Bedrooms
4
Bathrooms
4
Stories
3
Style
3-Storey
Construction Materials
Brick
Approx Age
100+
Basement
Apartment
Features / Amenities
Kitchens Total
4
Kitchen Plus
3 + 1
+ Bedrooms
1
Direction Faces
South
Parking Features
Lane, Private, Reserved/Assigned
Parking Spaces
4
Cooling
Wall Unit(s)
Heat Type
Baseboard
Heat Source
Electric
Property Features
Property Features
Library, Park, Place Of Worship, Public Transit, School
Sq. Ft.
3000-3500
Sewer
Sewer
Directions
Winchester & Parliament
Tax and Financial Info
Tax Annual Amount
$12,353.71
Tax Year
2026
Listing Office
Listing provided courtesy of Royal Lepage Terrequity Sw Realty.
Rooms
| Level | Size | Features | |
| Kitchen | Third | 15.58 X 5.51 | Laminate,Eat-in Kitchen,Window |
| Bedroom | Second | 13.16 X 9.68 | Hardwood Floor,Closet,Window |
| Living Room | Third | 16.57 X 12.83 | W/O To Terrace,Hardwood Floor,Combined w/Dining |
| Bedroom | Lower | 13.48 X 10.01 | Broadloom,Window,Closet |
| Living Room | Second | 23.26 X 15.26 | Laminate,Bay Window,Combined w/Dining |
| Living Room | Lower | 23.10 X 15.42 | Laminate,Window,Combined w/Dining |
| Family Room | Second | 16.34 X 9.74 | Laminate,Window,Pass Through |
| Bedroom | Third | 15.75 X 10.76 | Laminate,Window,Closet |
| Kitchen | Lower | 12.99 X 6.99 | Open Concept,Window,Tile Floor |
| Bedroom | Main | 13.26 X 15.26 | Broadloom,Window,Double Closet |
| Living Room | Main | 23.10 X 15.42 | Bay Window,Hardwood Floor,Combined w/Dining |
| Family Room | Main | 16.34 X 9.74 | Hardwood Floor,Window |
| Family Room | Lower | 16.34 X 9.74 | W/O To Yard,Tile Floor |
| Kitchen | Main | 14.34 X 7.09 | Pass Through,Tile Floor,W/O To Balcony |
| Kitchen | Second | 7.78 X 7.09 | Laminate,W/O To Balcony,Window |
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Listing Information Last Updated 9/18/2026
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