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29 Winchester Street, Toronto, ON M4X1A6

$3,400,0004Beds 4Baths 3,000Sqft Cabbagetown-South St. James Town

Property Overview

  • Row / Townhouse Home Type
  • Fourplex Building Type
  • 4043 Sqft Lot Size
  • 4 Beds
  • 4 Full Baths
  • Air Conditioning (Wall Unit(s)) Cooling
  • 0 Half Baths
  • 4 Parking Space(s)
  • 1926 Year Built
  • Property Taxes
  • 43 days Days on Market
  • C13578164 MLS® #
  • $1,133 Price / Sqft
  • Three Storey Style
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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. 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.

Interior Details

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Baseboard
Air Conditioning (Wall Unit(s))
0
None
Part

Exterior Details

Brick
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Other
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More Information

Property

Park, Schools Nearby
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Parking

Yes
4
No Garage

Utilities

Municipal / City

Data is supplied by the Toronto Regional Real Estate Board (TRREB) MLS® System. TRREB is the owner of the copyright in its MLS® System. Data is deemed reliable but is not guaranteed accurate by TRREB. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by The Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA. Used under license.
Data was last updated Tuesday, July 21, 2026, 5:34:10 AM UTC.