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$3,400,000

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29 Winchester Street

Cabbagetown-South St. James Town, Toronto, Ontario M4X1A6

For sale· Added

3+1 bed4 bath3,000–3,500 sqft

About this home

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.

Location

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Property details

Listing

MLS® number
C13578164
Added
Jul 17, 2026 ()
Updated
Jul 20, 2026 ()
Info refreshed

Overview

Property type
Multi-family
Building type
Fourplex
Storeys
3

Inside

Bedrooms
3+1
Bathrooms
4
Heating
Baseboard heaters, Forced air, Electric, Natural gas
Cooling
Wall unit
Fireplace
Yes
Flooring
Tile, Hardwood, Laminate, Carpeted
Appliances
Refrigerator, Dishwasher, Stove
Features
Lane

Building

Basement
Apartment in basement
Exterior
Brick
Parking
No Garage · 4 spaces

Land

Lot size
28.5 x 142 ft

Services

Water
Municipal water
Sewer
Sanitary sewer

Location

Cross streets
Winchester & Parliament

Running costs

Annual property tax
$12,354

Rooms

Living roomMain level7.04 x 4.7 m
BedroomThird level4.8 x 3.28 m
Living roomLower level7.04 x 4.7 m
KitchenLower level3.96 x 2.13 m
Family roomLower level4.98 x 2.97 m
BedroomLower level4.11 x 3.05 m
KitchenMain level4.37 x 2.16 m
Family roomMain level4.98 x 2.97 m
BedroomMain level4.04 x 4.65 m
Living roomSecond level7.09 x 4.65 m
KitchenSecond level2.37 x 2.16 m
Family roomSecond level4.98 x 2.97 m
BedroomSecond level4.01 x 2.95 m
Living roomThird level5.05 x 3.91 m
KitchenThird level4.75 x 1.68 m

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$3,400,000
29 Winchester Street
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