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← All Listings|For SaleMLS® C13578164

29 Winchester Street

Toronto (Cabbagetown-South St. James Town), Ontario, M4X 1A6

Also listed as 29 Winchester St., Toronto (Cabbagetown-South St. James Town), Ontario, M4X 1A6

$3,400,000
Listed July 17, 2026
4
Bedrooms
4
Bathrooms
15
Rooms
Multi-family
Type
28.5 x 142 FT
Lot
No Garage
Parking

Key Features

Cooling: Wall unit
Heating: Baseboard heaters, Forced air, Electric, Natural gas
Basement: Apartment in basement, N/A
Parking: No Garage
Directions: Winchester & Parliament

Property Description

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. (id:64869)

Property Details

Home Snapshot
MLS® NumberC13578164
StatusFor Sale
Property TypeMulti-family
Bedrooms4
Bathrooms4
Storeys3
Lot Dimensions28.5 x 142 FT
Listed2026-07-17
Condo Fees & Taxes
Property Taxes$12,354
Lot, Views & Setting
Lot FeaturesLane
DirectionsWinchester & Parliament
Construction & Systems
Exterior FeaturesBrick
FlooringTile, Hardwood, Laminate, Carpeted
BasementApartment in basement, N/A
HeatingBaseboard heaters, Forced air, Electric, Natural gas
CoolingWall unit
Water SourceMunicipal water
SewersSanitary sewer
Parking & Access
Parking Total4
Parking FeaturesNo Garage
Bedrooms Above Grade3
Bedrooms Below Grade1
Property AttachedYes
Room-by-Room Layout

Main level

Living room—
Kitchen—
Family room—
Bedroom—

Third level

Bedroom—
Living room—
Kitchen—

Lower level

Living room—
Kitchen—
Family room—
Bedroom—

Second level

Living room—
Kitchen—
Family room—
Bedroom—
Listing Timeline
Original EntryJul 17, 2026, 3:30 p.m.
Status ChangedJul 20, 2026, 1:30 p.m.
Photo Count50
Photos UpdatedJul 17, 2026, 3:30 p.m.
Last UpdatedJul 20, 2026, 1:40 p.m.

Frequently Asked Questions

Where is 29 Winchester Street located?+

29 Winchester Street is located in Toronto (Cabbagetown-South St. James Town), ON (M4X1A6).

How much is 29 Winchester Street?+

29 Winchester Street is listed for sale at $3,400,000.

How many bedrooms and bathrooms does 29 Winchester Street have?+

This home offers 4 bedrooms and 4 bathrooms.

What type of property is 29 Winchester Street?+

It is a home.

What are the property taxes for 29 Winchester Street?+

Annual property taxes are approximately $12,354.

Is there parking at 29 Winchester Street?+

Yes — 29 Winchester Street includes a 4-car garage.

How can I book a showing or learn more about 29 Winchester Street, Toronto (Cabbagetown-South St. James Town)?+

Contact Barbara Beers and the Barbara Beers Real Estate team at +1-905-634-2335 or barbara@barbarabeers.com to book a private showing or request more details.

Lisa Shirriff
Lisa Shirriff
Broker

ROYAL LEPAGE TERREQUITY SW REALTY

Direct: 416-495-2746

Mortgage Calculator

Purchase Price

$3,400,000
5.25%
$680,000
Est. Monthly Payment
Principal & Interest only
$16,300

Estimate only. Does not include property taxes, insurance, or fees. Actual rates may vary. Contact us for personalized mortgage guidance.

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Listing Brokerage: ROYAL LEPAGE TERREQUITY SW REALTY

Co-Listing Brokerage: ROYAL LEPAGE TERREQUITY SW REALTY

Advertised By: Royal LePage® Burloak Real Estate Services

MLS®, REALTOR®, and associated logos are trademarks of CREA.

Location

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29 Winchester St., Toronto (Cabbagetown-South St. James Town), Ontario, M4X 1A6

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