29 Winchester St
Toronto, Ontario
Beds
4
Baths
4
Sqft
3,000
Type
Fourplex
About this Property
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. With over 4200+ sq ft of living space (each unit is over 1000+ sq. ft in size), 29 Winchester offers a spacious and gracious living environment, complimented with multiple walk-out balconies, large windows, private decks and terraces, all 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 ensuite laundry in each unit. Parking is accessed via a private rear laneway (4 parking spaces at present including 1 tandem space, and the possibility to expand up to 6 car parking on site). Highly desirable 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.
Listing Details
- MLS #
- C14111438
- Board
- PROPTX
- Market
- ontario
- Property Type
- Fourplex
- Style
- 3-Storey
- Year Built
- 100+
- Garage
- None
- Parking Spaces
- 4
- Basement
- Apartment
- Heating
- Baseboard
- Cooling
- Wall Unit
- Pool
- None
- Lot Size
- 28.47 × 132.73 ft
- Annual Taxes
- $12,354/yr
- Listed By
- ROYAL LEPAGE TERREQUITY SW REALTY
- Listed On
- October 22, 2026
Features & Extras
Extras
Sale includes all existing appliances and fixtures, excluding tenants personal effects. 4x fridges, 4 stoves, 4x dishwashers, 3x air conditioners, 1x gas burner plus electrical(owned), HWT (rental), 4 fireplaces (as-is), 4x dishwashers). Full list of renovations / improvements included with attachments.
Room Measurements
| Room | Level | Size | Features |
|---|---|---|---|
| Living | Main | 4.7 × 7.04 m | Bay Window, hardwood floor, Combined W/Dining |
| Kitchen | Main | 2.16 × 4.37 m | Pass Through, Tile Floor, W/O To Balcony |
| Family | Main | 2.97 × 4.98 m | hardwood floor, Window |
| Br | Main | 4.65 × 4.04 m | Broadloom, Window, Double Closet |
| Living | 2nd | 4.65 × 7.09 m | Laminate, Bay Window, Combined W/Dining |
| Kitchen | 2nd | 2.16 × 2.37 m | Laminate, W/O To Balcony, Window |
| Family | 2nd | 2.97 × 4.98 m | Laminate, Window, Pass Through |
| Br | 2nd | 2.95 × 4.01 m | hardwood floor, Closet, Window |
| Living | 3rd | 3.91 × 5.05 m | W/O To Terrace, hardwood floor, Combined W/Dining |
| Kitchen | 3rd | 1.68 × 4.75 m | Laminate, Eat-In Kitchen, Window |
| Br | 3rd | 3.28 × 4.8 m | Laminate, Window, Closet |
| Living | Lower | 4.7 × 7.04 m | Laminate, Window, Combined W/Dining |
| Kitchen | Lower | 2.13 × 3.96 m | Open Concept, Window, Tile Floor |
| Family | Lower | 2.97 × 4.98 m | W/O To Yard, Tile Floor |
| Br | Lower | 3.05 × 4.11 m | Broadloom, Window, Closet |
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