$2,900,000
31.13 BTC
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29 Winchester Street, Toronto
$2,900,000
PRICE
3 + 1
BEDROOMS
4
BATHROOMS
C14111438
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. With over 4200+ sq ft of living space (each unit is over 1000+ sq. ft in size), 29 Winchester offers a spacious and gracious living environment, complimented with multiple walk-out balconies, large windows, private decks and terraces, all 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 ensuite laundry in each unit. Parking is accessed via a private rear laneway (4 parking spaces at present including 1 tandem space, and the possibility to expand up to 6 car parking on site). Highly desirable 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. Building financials available upon request. 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
C14111438
Property Type
Fourplex
Property Category
Bedrooms
3 + 1
Bathrooms
4
Kitchens
3 + 1
Taxes (Annual)
$12,353.71
Tax Year
2026
Published
October 23, 2026
Days on Market
5 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, 4 stoves, 4x dishwashers, 3x air conditioners, 1x gas burner plus electrical(owned), HWT (rental), 4 fireplaces (as-is), 4x dishwashers). 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
Architectural Style
3-Storey
Roof
Asphalt Shingle, Metal
Construction Materials
Brick
Lot Width
28 Feet
Lot Depth
133 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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