29 Winchester Street, Toronto, ON M4X 1A6

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.

• Inside a Toronto Heritage Conservation District — Cabbagetown Northwest

  HCD rules restrict exterior alterations and demolition — review the district plan before planning changes.

  Source: City of Toronto — Heritage Conservation Districts · as of Sep 2026

Also checked, nothing flagged at this location: flood hazard mapping, conservation-regulated areas, provincially significant wetlands, the Greenbelt, the Oak Ridges Moraine, the Niagara Escarpment plan, areas of natural and scientific interest, rail corridors, hydro transmission corridors.

Screened against public government mapping at this home’s location — simplified boundaries, not a survey, an appraisal or a legal determination. Confirm anything that matters with the authority named.