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29 Winchester Street

Toronto (Cabbagetown-South St. James Town), Ontario M4X1A6

MLS # C13578164

$3,400,000

Property Details

Type

Fourplex

Beds

4

Baths

4

Status

For Sale

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.

Mortgage Estimate

Estimated monthly payment

Calculating…

Estimate only. Taxes, insurance, condo fees, and lender terms are not included.

Monthly costs to verify

Property taxes: about $1,029/month based on listed annual taxes.

Estimate only. Confirm taxes, condo/maintenance fees, insurance, utilities, and lender terms before making decisions.

Rooms

Room Level Dimensions
Living room Main level 7.04 x 4.7
Bedroom Third level 4.8 x 3.28
Living room Lower level 7.04 x 4.7
Kitchen Lower level 3.96 x 2.13
Family room Lower level 4.98 x 2.97
Bedroom Lower level 4.11 x 3.05
Kitchen Main level 4.37 x 2.16
Family room Main level 4.98 x 2.97
Bedroom Main level 4.04 x 4.65
Living room Second level 7.09 x 4.65
Kitchen Second level 2.37 x 2.16
Family room Second level 4.98 x 2.97
Bedroom Second level 4.01 x 2.95
Living room Third level 5.05 x 3.91
Kitchen Third level 4.75 x 1.68

Facts & Location

Parking

4 spaces

Lot Size

28.5 x 142 FT

Annual Taxes

$12,354

Listing data

Listing information is provided for personal, non-commercial use and should be independently verified before making real estate decisions.

Last refreshed: Aug 17, 2026 4:15 AM

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