$2,900,000
29 Winchester St
Toronto C08, ON M4X 1A6
29 Winchester St, Toronto C08 — Listed at $2,900,000. 4 bedroom, 4 bathroom 3-Storey Fourplex. MLS® C14111438.
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Description
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. Building financials available upon request. 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 Details
Property Insights
Listing Courtesy of: ROYAL LEPAGE TERREQUITY SW REALTY
MLS® #C14111438


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HouseIndex Take: 29 Winchester Street
This fourplex (3-Storey) is located in the Cabbagetown-South St. James Town neighbourhood of Toronto.
The home offers 4+1 bedrooms, 4 bathrooms.
Features include a apartment basement, 4 parking spaces, a fireplace.
Additional details: lot dimensions of 28.47 × 132.73 feet.
Listed at $2,900,000 CAD with annual property taxes of $12,353.71 (2026).
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About Toronto Real Estate
This Fourplex is located in the Cabbagetown-South St. James Town community in Toronto. Toronto is Canada's largest city and the economic hub of the Greater Toronto Area. With world-class transit, diverse neighbourhoods from the Annex to Scarborough, and proximity to major employers in the Financial District, it remains the most sought-after real estate market in Ontario. Buyers benefit from extensive GO Transit and TTC subway connectivity.

















































