For Sale MLS® C13578164

29 Winchester Street

Cabbagetown-South St. James Town · Toronto C08 · ON · M4X 1A6

On market 64 days

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4 Beds
4 Baths
4 Parking
28.5 ft frontage Lot
Other Type
100+ Age

About this property

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.

Key facts

Type Fourplex · 3-Storey
Lot 28.5 ft frontage
Taxes $12,354/yr
Days on market 64
Neighbourhood Cabbagetown-South St. James Town
Property details
Property type Fourplex
Style 3-Storey
Age 100+
Rooms & baths
Bedrooms above / below 3 · 1
Building & utilities
Basement Apartment
Parking
Total 4
Lot
Width / Depth 28.5 ft
Financial
Taxes $12,354/yr
Features & amenities

Interior

None

Mortgage calculator

$15,885/moMonthly payment
$2,720,000Mortgage amount
$2,045,502Total interest
$5,445,502Total cost

Location

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Market Overview

Toronto C08

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MLS® C13578164 Brokerage ROYAL LEPAGE TERREQUITY SW REALTY Listed Jul 17, 2026 Updated Jul 20, 2026

Listing data provided by the Toronto Regional Real Estate Board (TRREB).

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The listing data is provided under copyright by the Toronto Regional Real Estate Board (TRREB). The listing 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.

Last updated: September 19, 2026.

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