
For Lease: 27 Rean Drive 306, Toronto, ON M2K 0A6, Toronto C15, ON
November 10, 2026
For Sale: 455 Rosewell Avenue 205, Toronto, ON M4R 2H9, Toronto C04, ON
November 10, 2026
29 Winchester Street, Toronto
Key facts
Monthly payment estimate
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About this unit
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.
Listed by: ROYAL LEPAGE TERREQUITY SW REALTY, Brokerage
Listing information provided by the Toronto Regional Real Estate Board (TRREB) MLS® System via PropTx. Information is believed to be accurate but is not guaranteed. MLS®, REALTOR® and the associated logos are trademarks of the Canadian Real Estate Association.


