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29 Winchester Street — Fourplex

For Sale

Toronto, ON M4X 1A6

4 Bed · 4 Bath · Fourplex

MLS #C13578164

$3,400,000

Listed Price

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.

Property Details

Bedrooms

4

Bathrooms

4

Square Feet

3000-3500 sqft

Property Type

Fourplex

Style3-Storey
Approx. Age100+ years
Lot Size28 142 ft
Frontage28.5 ft
Depth142.0 ft
GarageNone
BasementApartment
CoolingWall Unit(s)
HeatingBaseboard
FireplaceYes
Parking Spaces4
Listed OnJul 16, 2026
MLS Size3000-3500
Property Tax$12,354/year

Rooms

NameSize (m)Size (ft)Features
Living Room(Main)7.04 x 4.723.1 x 15.4-
Living Room(Main)7.04 x 4.723.1 x 15.4-
Living Room(Main)7.04 x 4.723.1 x 15.4-
Living Room(Main)7.04 x 4.723.1 x 15.4-
Living Room(Main)7.04 x 4.723.1 x 15.4-
Living Room(Main)7.04 x 4.723.1 x 15.4-
Living Room(Main)7.04 x 4.723.1 x 15.4-
Living Room(Main)7.04 x 4.723.1 x 15.4-
Kitchen(Main)4.37 x 2.1614.3 x 7.1-
Kitchen(Main)4.37 x 2.1614.3 x 7.1-
Kitchen(Main)4.37 x 2.1614.3 x 7.1-
Kitchen(Main)4.37 x 2.1614.3 x 7.1-
Kitchen(Main)4.37 x 2.1614.3 x 7.1-
Kitchen(Main)4.37 x 2.1614.3 x 7.1-
Kitchen(Main)4.37 x 2.1614.3 x 7.1-
Kitchen(Main)4.37 x 2.1614.3 x 7.1-
Family Room(Main)4.98 x 2.9716.3 x 9.7-
Family Room(Main)4.98 x 2.9716.3 x 9.7-
Family Room(Main)4.98 x 2.9716.3 x 9.7-
Family Room(Main)4.98 x 2.9716.3 x 9.7-
Family Room(Main)4.98 x 2.9716.3 x 9.7-
Family Room(Main)4.98 x 2.9716.3 x 9.7-
Family Room(Main)4.98 x 2.9716.3 x 9.7-
Family Room(Main)4.98 x 2.9716.3 x 9.7-
Bedroom(Main)4.04 x 4.6513.3 x 15.3-
Bedroom(Main)4.04 x 4.6513.3 x 15.3-
Bedroom(Main)4.04 x 4.6513.3 x 15.3-
Bedroom(Main)4.04 x 4.6513.3 x 15.3-
Bedroom(Main)4.04 x 4.6513.3 x 15.3-
Bedroom(Main)4.04 x 4.6513.3 x 15.3-
Bedroom(Main)4.04 x 4.6513.3 x 15.3-
Bedroom(Main)4.04 x 4.6513.3 x 15.3-
Living Room(Second)7.09 x 4.6523.3 x 15.3-
Living Room(Second)7.09 x 4.6523.3 x 15.3-
Living Room(Second)7.09 x 4.6523.3 x 15.3-
Living Room(Second)7.09 x 4.6523.3 x 15.3-
Living Room(Second)7.09 x 4.6523.3 x 15.3-
Living Room(Second)7.09 x 4.6523.3 x 15.3-
Living Room(Second)7.09 x 4.6523.3 x 15.3-
Living Room(Second)7.09 x 4.6523.3 x 15.3-
Kitchen(Second)2.37 x 2.167.8 x 7.1-
Kitchen(Second)2.37 x 2.167.8 x 7.1-
Kitchen(Second)2.37 x 2.167.8 x 7.1-
Kitchen(Second)2.37 x 2.167.8 x 7.1-
Kitchen(Second)2.37 x 2.167.8 x 7.1-
Kitchen(Second)2.37 x 2.167.8 x 7.1-
Kitchen(Second)2.37 x 2.167.8 x 7.1-
Kitchen(Second)2.37 x 2.167.8 x 7.1-
Family Room(Second)4.98 x 2.9716.3 x 9.7-
Family Room(Second)4.98 x 2.9716.3 x 9.7-
Family Room(Second)4.98 x 2.9716.3 x 9.7-
Family Room(Second)4.98 x 2.9716.3 x 9.7-
Family Room(Second)4.98 x 2.9716.3 x 9.7-
Family Room(Second)4.98 x 2.9716.3 x 9.7-
Family Room(Second)4.98 x 2.9716.3 x 9.7-
Family Room(Second)4.98 x 2.9716.3 x 9.7-
Bedroom(Second)4.01 x 2.9513.2 x 9.7-
Bedroom(Second)4.01 x 2.9513.2 x 9.7-
Bedroom(Second)4.01 x 2.9513.2 x 9.7-
Bedroom(Second)4.01 x 2.9513.2 x 9.7-
Bedroom(Second)4.01 x 2.9513.2 x 9.7-
Bedroom(Second)4.01 x 2.9513.2 x 9.7-
Bedroom(Second)4.01 x 2.9513.2 x 9.7-
Bedroom(Second)4.01 x 2.9513.2 x 9.7-
Living Room(Third)5.05 x 3.9116.6 x 12.8-
Living Room(Third)5.05 x 3.9116.6 x 12.8-
Living Room(Third)5.05 x 3.9116.6 x 12.8-
Living Room(Third)5.05 x 3.9116.6 x 12.8-
Living Room(Third)5.05 x 3.9116.6 x 12.8-
Living Room(Third)5.05 x 3.9116.6 x 12.8-
Living Room(Third)5.05 x 3.9116.6 x 12.8-
Living Room(Third)5.05 x 3.9116.6 x 12.8-
Kitchen(Third)4.75 x 1.6815.6 x 5.5-
Kitchen(Third)4.75 x 1.6815.6 x 5.5-
Kitchen(Third)4.75 x 1.6815.6 x 5.5-
Kitchen(Third)4.75 x 1.6815.6 x 5.5-
Kitchen(Third)4.75 x 1.6815.6 x 5.5-
Kitchen(Third)4.75 x 1.6815.6 x 5.5-
Kitchen(Third)4.75 x 1.6815.6 x 5.5-
Kitchen(Third)4.75 x 1.6815.6 x 5.5-
Bedroom(Third)4.8 x 3.2815.7 x 10.8-
Bedroom(Third)4.8 x 3.2815.7 x 10.8-
Bedroom(Third)4.8 x 3.2815.7 x 10.8-
Bedroom(Third)4.8 x 3.2815.7 x 10.8-
Bedroom(Third)4.8 x 3.2815.7 x 10.8-
Bedroom(Third)4.8 x 3.2815.7 x 10.8-
Bedroom(Third)4.8 x 3.2815.7 x 10.8-
Bedroom(Third)4.8 x 3.2815.7 x 10.8-
Living Room(Lower)7.04 x 4.723.1 x 15.4-
Living Room(Lower)7.04 x 4.723.1 x 15.4-
Living Room(Lower)7.04 x 4.723.1 x 15.4-
Living Room(Lower)7.04 x 4.723.1 x 15.4-
Living Room(Lower)7.04 x 4.723.1 x 15.4-
Living Room(Lower)7.04 x 4.723.1 x 15.4-
Living Room(Lower)7.04 x 4.723.1 x 15.4-
Living Room(Lower)7.04 x 4.723.1 x 15.4-
Kitchen(Lower)3.96 x 2.1313.0 x 7.0-
Kitchen(Lower)3.96 x 2.1313.0 x 7.0-
Kitchen(Lower)3.96 x 2.1313.0 x 7.0-
Kitchen(Lower)3.96 x 2.1313.0 x 7.0-
Kitchen(Lower)3.96 x 2.1313.0 x 7.0-
Kitchen(Lower)3.96 x 2.1313.0 x 7.0-
Kitchen(Lower)3.96 x 2.1313.0 x 7.0-
Kitchen(Lower)3.96 x 2.1313.0 x 7.0-
Family Room(Lower)4.98 x 2.9716.3 x 9.7-
Family Room(Lower)4.98 x 2.9716.3 x 9.7-
Family Room(Lower)4.98 x 2.9716.3 x 9.7-
Family Room(Lower)4.98 x 2.9716.3 x 9.7-
Family Room(Lower)4.98 x 2.9716.3 x 9.7-
Family Room(Lower)4.98 x 2.9716.3 x 9.7-
Family Room(Lower)4.98 x 2.9716.3 x 9.7-
Family Room(Lower)4.98 x 2.9716.3 x 9.7-
Bedroom(Lower)4.11 x 3.0513.5 x 10.0-
Bedroom(Lower)4.11 x 3.0513.5 x 10.0-
Bedroom(Lower)4.11 x 3.0513.5 x 10.0-
Bedroom(Lower)4.11 x 3.0513.5 x 10.0-
Bedroom(Lower)4.11 x 3.0513.5 x 10.0-
Bedroom(Lower)4.11 x 3.0513.5 x 10.0-
Bedroom(Lower)4.11 x 3.0513.5 x 10.0-
Bedroom(Lower)4.11 x 3.0513.5 x 10.0-

Available For Sale Nearby

Available Nearby

OQ

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OVAIS QASSIM

Broker of Record

PREMIER MATRIX REALTY LTD. BROKERAGE

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Home Features

Property TypeFourplex
Style3-Storey
Approx. Age100+ years
Lot Size28 × 142 ft
Frontage28.5 ft
Depth142.0 ft
GarageNone
BasementApartment
CoolingWall Unit(s)
FireplaceYes

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About 29 Winchester Street, Toronto, ON M4X 1A6

29 Winchester Street, Toronto, ON M4X 1A6 is a 4-bedroom, 4-bathroom 3-storey fourplex with approximately 3000-3500 square feet of living space, situated on a 28 142 foot lot. This property is currently for sale at $3,400,000. The home features a none garage and a apartment basement, built approximately 100+ years ago.

Cabbagetown-South St. James Town Neighbourhood

This home is located in Cabbagetown-South St. James Town, part of Toronto C08 in the Toronto area. Explore more homes for sale and recently sold properties in this neighbourhood.

Whether you are looking to buy, sell, or lease in Cabbagetown-South St. James Town, our team of experienced real estate professionals can help you navigate the market and find the perfect home. Contact us today for a free consultation.

29 Winchester Street, Toronto, ON M4X 1A6

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