




4 Beds
4 Baths
C$2,900,000
29 Winchester Street, Toronto, Toronto C08 ON, M4X 1A6
Property typeMulti-family
Overview
Active
New
Listed Oct 23, 2026
Updated 2 days ago
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.
Additional information
- MLS® ID
- C14111438
Interior Features
- Bedrooms
- 4
- Bathrooms
- 4
- Fireplace
- Yes
- Cooling
- Yes
- Heating
- Yes
- Basement
- Yes
Other Property Details
- Taxes
- $12,354
- Tax Frequency
- Annually
Courtesy of Listed by , ROYAL LEPAGE TERREQUITY SW REALTY,
Based on information from the Toronto Regional Real Estate Board. The information provided herein must only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate and may not be used for any commercial purpose or any other purpose. Information is deemed reliable but is not guaranteed accurate.
©2026 Toronto Real Estate Board. All rights reserved.
Data last updated 3:39 AM UTC, 10/28/2026