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29 Winchester Street

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

ActiveFor Sale
4 Beds
4 Baths
3,000 Sq Ft
Multi-Family
Virtual Tour Available

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

StatusActive
Property TypeMulti-Family
Listing TypeFor Sale
Interior Size3,000 sq ft
Bedrooms4
Bathrooms4
ListedJuly 17, 2026
Postal CodeM4X 1A6

Features & Amenities

  • View
  • Fireplace
  • Air Conditioning
  • Basement

TRREB MLS® Attribution

MLS® C13578164

Listed by ROYAL LEPAGE TERREQUITY SW REALTY

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. The trademarks REALTOR®, REALTORS® and the REALTOR® logo are controlled by CREA and identify real estate professionals who are members of CREA. Listing data provided by the Toronto Regional Real Estate Board (TRREB). The information contained herein is from sources believed to be reliable but is not guaranteed. Information deemed reliable but not guaranteed accurate by TRREB or Team Filipe / RE/MAX.

$3,400,000

asking price

MLS®C13578164
TypeMulti-Family
CityToronto C08
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Team Filipe · RE/MAX · (647) 210-6070

Mortgage Estimate

Est. Monthly Payment

$16,603

/month · $2,720,000 mortgage

Down Payment20% — $680,000
Interest Rate5.5%

Amortization

Total Interest

$2,260,794

Total Cost

$4,980,794

Estimate only. Based on Canadian semi-annual compounding, 25-yr amortization at 5.5%.

Full Mortgage Calculator →

Listed By

ROYAL LEPAGE TERREQUITY SW REALTY