29 Winchester Street

ActiveRegent Park / Cabbagetown / St. James Town · Cabbagetown-South St. James Town20 days on marketMLS® C13578164

$3,400,000

$1,133 / sq ft

Bedrooms4

Bathrooms4

Interior3,000 sq ft

TypeMulti-Family

ListingFor Sale

Days on Market20

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.

Features & finishes

View

Fireplace

Air Conditioning

Basement

Property details

MLS® Number	C13578164
Status	Active
Listing Type	For Sale
Property Type	Multi-Family
Interior Size	3,000 sq ft
Beds / Baths	4 bed · 4 bath
Neighbourhood	Cabbagetown-South St. James Town
City	Regent Park / Cabbagetown / St. James Town
Postal Code	M4X 1A6
Province	ON
Listed Date	July 17, 2026
Days on Market	20
Price per Sq Ft	$1,133
Brokerage	ROYAL LEPAGE TERREQUITY SW REALTY