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Fourplex for sale at 29 Winchester Street, Toronto C08 - 4 bedroom, 4 bathroom - Photo 1 of 36
Fourplex for sale at 29 Winchester Street, Toronto C08 - 4 bedroom, 4 bathroom - Photo 2 of 36
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Fourplex for sale at 29 Winchester Street, Toronto C08 - 4 bedroom, 4 bathroom - Photo 9 of 36
Fourplex for sale at 29 Winchester Street, Toronto C08 - 4 bedroom, 4 bathroom - Photo 10 of 36
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Fourplex for sale at 29 Winchester Street, Toronto C08 - 4 bedroom, 4 bathroom - Photo 12 of 36
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$3,400,000

29 Winchester St

Toronto C08, ON M4X 1A6

29 Winchester St, Toronto C08Listed at $3,400,000. 4 bedroom, 4 bathroom 3-Storey Fourplex. MLS® C13578164.

Possession · seller's timeline

Flexible

4Beds
4Baths
3000-3500sqft
Fourplex
3-Storey
4Parking
$12,353.71Taxes/yr · 2026

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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.

Property Details

Property TypeFourplex
Style3-Storey
CommunityCabbagetown-South St. James Town
Approximate Age100+
Rooms15
Kitchens4
Washrooms4
Square Feet3000-3500 sqft
Lot Dimensions28.47 × 142 ft
Fronting OnSouth
Dir/Cross StWinchester & Parliament
Garage TypeNone
DriveLane, Private, Reserved/Assigned
Parking Drive Spaces4
Total Parking Spaces4
ExteriorBrick
RoofUnknown
FoundationUnknown
BasementApartment
Fireplace FeaturesYes
Heating TypeBaseboard
Heating SourceElectric
A/CWall Unit(s)
SewersSewer
Taxes (2026)$12,353.71
HSTNot Subject to HST
SecurityNone
UFFINo
Listed Date7/17/2026
Days on Market50 days
PossessionTBD

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Listing Courtesy of: ROYAL LEPAGE TERREQUITY SW REALTY

MLS® #C13578164

TRREBMLS®

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 REALTOR®, REALTORS®, and the REALTOR® logo are controlled by The Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by CREA and identify the quality of services provided by real estate professionals who are members of CREA. Used under license.

© 2026 Toronto Regional Real Estate Board. All rights reserved.

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HouseIndex Take: 29 Winchester Street

This fourplex (3-Storey) is located in the Cabbagetown-South St. James Town neighbourhood of Toronto.

The home offers 4+1 bedrooms, 4 bathrooms.

Features include a apartment basement, 4 parking spaces, a fireplace.

Additional details: lot dimensions of 28.47 × 142 feet.

Listed at $3,400,000 CAD with annual property taxes of $12,353.71 (2026).

About Toronto Real Estate

This Fourplex is located in the Cabbagetown-South St. James Town community in Toronto. Toronto is Canada's largest city and the economic hub of the Greater Toronto Area. With world-class transit, diverse neighbourhoods from the Annex to Scarborough, and proximity to major employers in the Financial District, it remains the most sought-after real estate market in Ontario. Buyers benefit from extensive GO Transit and TTC subway connectivity.

TTC subway & streetcar networkWorld-class dining & entertainmentUniversity of Toronto & major hospitals nearbyWaterfront trails & ravine parks
Walkability: Highly walkable — many neighbourhoods score 80+ on Walk Score
View full Toronto neighbourhood guide →