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MLS® C14111438
Cabbagetown-South St.James Town, Toronto, ON
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. Shows 10+ and must be seen - a perfect addition for any investor seeking a high calibre investment grade property to add to their portfolio.
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.
Broker
ROYAL LEPAGE TERREQUITY SW REALTY
Neighbourhood
Cabbagetown-South St.James Town
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Fourplex
29 Winchester Street Toronto
Cabbagetown-South St.James Town
Built
100+
Type
Fourplex
Basement
Apartment
Parking
None (4)
Property Tax
~$12,354/yr
Heating
Baseboard
Buying Essentials
Square Feet
3250 sqft
Facing Direction
South
Parking
None (4)
Finances
List Price
$2,900,000
Price per SQFT
$892/sqft
Property Tax
~$12,354/yr
Property Specs
Property Type
Fourplex
MLS Size
3250 sqft
Age of Building
100+
Basement
Apartment
Living & Amenities
Heating Type
Baseboard
Features
None
Policies & Utilities
Neighbourhood
Cabbagetown-South St.James Town
Listed On
Oct 22, 2026
Library
Park
Place Of Worship
Public Transit
School
Days on Market
Current: 15 days
Bay Window, Hardwood Floor, Combined w/Dining
23.1 x 15.4
356 sqft
Pass Through, Tile Floor, W/O To Balcony
14.3 x 7.1
102 sqft
Hardwood Floor, Window
16.3 x 9.7
159 sqft
Broadloom, Window, Double Closet
13.3 x 15.3
202 sqft
Laminate, Bay Window, Combined w/Dining
23.3 x 15.3
355 sqft
Laminate, W/O To Balcony, Window
7.8 x 7.1
55 sqft
Laminate, Window, Pass Through
16.3 x 9.7
159 sqft
Hardwood Floor, Closet, Window
13.2 x 9.7
127 sqft
W/O To Terrace, Hardwood Floor, Combined w/Dining
16.6 x 12.8
213 sqft
Laminate, Eat-in Kitchen, Window
15.6 x 5.5
86 sqft
Laminate, Window, Closet
15.7 x 10.8
169 sqft
Laminate, Window, Combined w/Dining
23.1 x 15.4
356 sqft
Open Concept, Window, Tile Floor
13.0 x 7.0
91 sqft
W/O To Yard, Tile Floor
16.3 x 9.7
159 sqft
Broadloom, Window, Closet
13.5 x 10.0
135 sqft
Rooms
15
Listed Room Area
2,724 sqft
Source
Estimated from MLS room dimensions
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