29 Winchester Street, Toronto, ON M4X 1A6
Toronto C08
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. 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.
Estimate only - excludes property tax, condo fees, utilities and home insurance. Rates vary by lender and term; based on semi-annual compounding.
Walkability, transit, and bike-friendliness for 29 Winchester Street, Toronto, ON M4X 1A6
Provided by Walk Score®. Walk Score, Transit Score, and Bike Score are trademarks of Walk Score.
MLS# C13578164
Listed by ROYAL LEPAGE TERREQUITY SW REALTY
On market since Jul 17, 2026
29 Winchester Street, Toronto, ON M4X 1A6 is listed for $3,400,000 CAD.
29 Winchester Street, Toronto, ON M4X 1A6 has 4 bedrooms and 4 bathrooms.
29 Winchester Street, Toronto, ON M4X 1A6 is a Fourplex.
29 Winchester Street, Toronto, ON M4X 1A6 is in Toronto C08, Ontario.
29 Winchester Street, Toronto, ON M4X 1A6 is currently for sale.
Contact Michael Mezheritsky to arrange a private showing of 29 Winchester Street, Toronto, ON M4X 1A6 (MLS# C13578164). You can also send a message through the contact form on this site.
