29 Winchester Street, Toronto, ON

Toronto, Central Toronto, Cabbagetown-South St. James Town Hood
Winchester & Parliament
3+1 Br | 4 Bath | 3000-3500 Sqft
$3,400,000 For Sale

Property Overview

  • Fourplex — 3-Storey
  • SqFt: | 3000-3500 Sqft
  • Lot Size: 28.47 x 142.00 Feet
  • Age: 100+ Years
  • Basement: Apartment
  • Exterior: Brick
  • Taxes: 12,354 / 2026
  • Zoning: n/a
  • MLS #: C13578164
  • Sewer: Sewer
  • Heat Source: Electric , Baseboard

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.

Sale includes all existing appliances and fixtures, excluding tenants personal effects. 4x fridges, 4x stoves, 4x dishwashers, 3x air conditioners, 1x gas burner plus electrical (owned), HWT (rental), 4 fireplaces (as-is). Full list of renovations / improvements included with attachments.

Property Details

  • For: For Sale
  • Type: Fourplex
  • Style: 3-Storey
  • Lot: 28.47 x 142.00 Feet
  • Region: Toronto
  • Hood: Cabbagetown-South St. James Town
  • Zoning: n/a
  • Lot Irreg: Fronting on: South
  • Fronting On: South

Building Details

  • Age: 100+ Years
  • Exterior: Brick
  • Heat: Electric , Baseboard
  • A/C: Wall Unit(s)
  • Interior Features: None
  • Pool: None
  • Sewer: Sewer
  • Garage: None
  • Total Parking: 4.00
  • Driveway: Lane, Private, Reserved/Assigned

Property Interior

  • Sqft: 3000-3500 Sqft
  • Bed: 3 +1
  • Bath: 4
  • Kitchen: 3 +1
  • Family Room: No
  • Basement: Apartment
Rooms Details

Living Room

Main Level

7.04 x 4.7

Bay Window, Hardwood Floor, Combined w/Dining

Kitchen

Main Level

4.37 x 2.16

Pass Through, Tile Floor, W/O To Balcony

Family Room

Main Level

4.98 x 2.97

Hardwood Floor, Window

Bedroom

Main Level

4.04 x 4.65

Broadloom, Window, Double Closet

Living Room

Second Level

7.09 x 4.65

Laminate, Bay Window, Combined w/Dining

Kitchen

Second Level

2.37 x 2.16

Laminate, W/O To Balcony, Window

Family Room

Second Level

4.98 x 2.97

Laminate, Window, Pass Through

Bedroom

Second Level

4.01 x 2.95

Hardwood Floor, Closet, Window

Living Room

Third Level

5.05 x 3.91

W/O To Terrace, Hardwood Floor, Combined w/Dining

Kitchen

Third Level

4.75 x 1.68

Laminate, Eat-in Kitchen, Window

Bedroom

Third Level

4.8 x 3.28

Laminate, Window, Closet

Living Room

Lower Level

7.04 x 4.7

Laminate, Window, Combined w/Dining

Kitchen

Lower Level

3.96 x 2.13

Open Concept, Window, Tile Floor

Family Room

Lower Level

4.98 x 2.97

W/O To Yard, Tile Floor

Bedroom

Lower Level

4.11 x 3.05

Broadloom, Window, Closet

Property Listed by: ROYAL LEPAGE TERREQUITY SW REALTY
Virtual Tour: https://www.winsold.com/tour/462753

Home Valuation Estimate

What is 29 Winchester Street, Toronto, ON worth in today’s Cabbagetown-South St. James Town, Central Toronto market?

This HomeZira valuation preview helps buyers and sellers think through the asking price for this 3-bedroom Fourplex with 3000-3500 sq. ft. in Cabbagetown-South St. James Town, Central Toronto. The full estimate reviews the property’s location, home type, bedroom count, size range, age, and nearby comparable market activity after sign-in.

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Location

  • Address: 29 Winchester Street
  • Neighborhood: Cabbagetown-South St. James Town
  • Zip/Postal Code: M4X 1A6
  • Nearby Amenities: Library, Park, Place Of Worship, Public Transit, School
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About 29 Winchester Street, Toronto, ON M4X 1A6, Central Toronto

Located at 29 Winchester Street, Toronto, ON in Central Toronto (Cabbagetown-South St. James Town neighbourhood), near Winchester & Parliament. This freehold home offers Fourplex, ["3-Storey"], 3 bedrooms, 4 bathrooms and 3000-3500 sq.ft. (approx.) in a layout suited to everyday family living. Basement: Apartment • 4 parking spots • Garage: None • Heating: Electric Baseboard • Cooling: Wall Unit(s). Property taxes are approximately $12,354 for 2026. 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.

FAQs for 29 Winchester Street, Toronto, ON , Cabbagetown-South St. James Town , Central Toronto

What are the listing details for 29 Winchester Street, Toronto, ON?
29 Winchester Street, Toronto, ON is a Fourplex for sale in Central Toronto, in the Cabbagetown-South St. James Town neighbourhood, Toronto. The current list price is $3,400,000. MLS number: C13578164.
How many bedrooms and bathrooms does this home have?
29 Winchester Street, Toronto, ON is listed as a Fourplex with a ["3-Storey"] style, featuring 3+1 bedroom(s) and 4 bathroom(s). The listed interior size range is 3000-3500 sq. ft..
What lot, basement, garage, or parking details are listed?
The lot size is listed as approximately 28.47 x 142.00 Feet. The basement is listed as: Apartment. Garage type: None. Total parking: 4 space(s).
What heating, cooling, and exterior details are shown?
Heating is listed as: Electric, Baseboard. Cooling is listed as: Wall Unit(s). Exterior/construction materials are listed as: Brick.
Where is this property located?
29 Winchester Street, Toronto, ON is located in the Cabbagetown-South St. James Town neighbourhood of Central Toronto. The listed cross street is Winchester & Parliament.
What information is available on this public listing page?
The public listing page shows current active listing information, property photos, room details when available, map location, listed price, property features, and contact options. Annual taxes are listed as $12,354 / 2026. Valuation tools and similar sold-property previews are available after sign-in where applicable, without displaying sold data in this public FAQ.

FAQ content is based on current active listing fields shown on this page. Sold prices, sold comparables, and VOW-only details are not included in this public FAQ.