$3,400,000
36.50 BTC
Photos
29 Winchester Street, Toronto
$3,400,000
PRICE
3 + 1
BEDROOMS
4
BATHROOMS
C13578164
MLSID

29 Winchester Street, Toronto

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.
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Summary

Address
29 Winchester Street
MLSID
C13578164
Property Type
Fourplex
Property Category
Bedrooms
3 + 1
Bathrooms
4
Kitchens
3 + 1
Taxes (Annual)
$12,353.71
Tax Year
2026
Published
July 17, 2026
Days on Market
40 Days
Possession Type
Flexible
Possession Details
Tbd
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Inclusions

Sale includes all existing appliances and fixtures, excluding tenants personal effects. 4x fridges, 4x stoves, 4x dishwashers, 3x air conditioners, 1x gas burner plus electrical (owned), HWT (rental), 4 fireplaces (as-is). Full list of renovations / improvements included with attachments.

Details

Property Features
Library, Park, Place Of Worship, Public Transit, School
Security Features
None
Bathroom 1
4-Piece Basement Level
Bathroom 2
3-Piece Second Level
Bathroom 3
3-Piece Third Level
Bathroom 4
4-Piece Main Level
Basement
Apartment
Interior Features
None
Parking Spaces
4
Parking Total
4
Parking Features
Lane, Private, Reserved/Assigned
Architectural Style
3-Storey
Roof
Unknown
Construction Materials
Brick
Lot Width
28 Feet
Lot Depth
142 Feet
Water
Municipal
Heat Source
Electric
Heat Type
Baseboard
New Construction
No
Occupant Type
Tenant
Private Entrance
No
Sauna
No
Seasonal Property
No
Hot Tub / Spa
No
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