29 Winchester Street, Toronto, ON M4X 1A6

About this home

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.

Home details

Days on market

Not reported

Property type

Fourplex

MLS® number

C14111438

Source status

New

Bedrooms

4

Bathrooms

4

Postal code

M4X 1A6

Kitchens

4

Kitchens above grade

3

Kitchens below grade

1

Family room / den

Yes

Interior size (reported range)

3000-3500 (units not reported)

Lot depth

132.73 ft

Garage parking spaces

Not reported

Total parking spaces

4

Occupancy

Tenant

Possession type

Flexible

Garage

None

Annual property tax

12353.71

Basement

Apartment

Interior features

None

Architectural style

3-Storey

Parking features

Lane, Private

Pool features

None

Fireplace

Yes

Waterfront

No

Elevator

No

Garage available

No

Heating system

Baseboard

Heating fuel

Electric

Cooling

Wall Unit(s)

Sewer

Sewer

Direction facing

South

Construction materials

Brick

Roof

Asphalt Shingle, Metal

Foundation

Unknown

MLS entry age (not confirmed DOM)

12 days

These details come from the listing source. Please confirm measurements and fees before making a decision.

Utilities and services

Sewer

Sewer

Heating system

Baseboard

Heating fuel

Electric

Cooling

Wall Unit(s)

A reported service is not necessarily included in rent or maintenance. Missing information does not mean a service is absent.

Room sizes

Bedrooms above grade

3

Bedrooms below grade

1

Rooms above grade

15

Den / family room reported

Yes

Room counts and measured room dimensions are separate source fields. No measurements are inferred.

Price history

Asking amount

$2,900,000

1. Oct 23, 2026

   Original MLS entry

   Entry into the source MLS system; distinct from days on market.

This history uses dates and prices supplied by the listing source. Some details may be missing.

Estimate monthly costs

Adjust the assumptions for your own scenario. Blank expenses are unknown; enter them for a fuller estimate.

Planning estimate with Canadian semiannual compounding. Excludes mortgage insurance, closing costs and special assessments. This is not a lender quote or mortgage approval.

Map and neighbourhood

Region / county

Toronto

Municipality

TORONTO

MLS® community

Cabbagetown-South St. James Town

MLS® district

Toronto C08