Listed by Royal Lepage Terrequity Sw Realty.

29 Winchester Street is a Fourplex, 3-Storey and is currently for Sale @ $3,400,000. Taxes in 2026 were $12,353.71.

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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. The 3-Storey on 29 Winchester Street has 3 bedrooms, 4 bathrooms, and is located on a 142 x 28.47 ft lot in the community of Cabbagetown-South St. James Town . 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.

Sale includes all existing appliances and fixtures, excluding tenants personal effects. 4x fridges, 4x stoves, 4x dishwashers, 3x air conditioners, 1x gas burner plus electrical (owned), HWT (rental), 4 fireplaces (as-is). Full list of renovations / improvements included with attachments.

The address 29 Winchester Street was listed for sale (MLS# C13578164) on Friday, July 17, 2026.