$3,400,000
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29 Winchester Street, Toronto (cabbagetown-South St. James Town), ON M4X1A6

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4 Beds
4 Baths
- Sq Ft

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:58753)

Listing By: LISA SHIRRIFF - ROYAL LEPAGE TERREQUITY SW REALTY
Source: CREA #C13578164 Listing provided courtesy of Canadian Real Estate Association
  • MLS® C13578164
  • Date Listed07/17/2026
  • Days on Realty 77 Days
  • Bedrooms 4
  • Bathrooms 4 baths
  • Lot Size -
  • Sewer Other
  • Property Type Quadruplex
  • Water Public

Interior Features

  • Appliances Refrigerator, Dishwasher, Stove
  • Flooring Tile, Hardwood, Laminate, Carpeted
  • Cooling Wall unit
  • Heating Baseboard heaters, Forced air, Electric, Natural gas

Exterior / Lot Features

  • Roof -
  • Lot Size Acres -
  • Lot Size SQFT -
  • Lot Features Lane

Directions

Winchester & Parliament

Sales & Tax History

Source: Public Records

Local Neighborhood Highlights for M4X1A6

Discover key demographics, population statistics, and environmental insights for the Toronto (cabbagetown-South St. James Town), ON area.

Walkability in ON / M4X1A6

Source: Walk Score

95/100

Walker's Paradise

Walk Score ®

92/100

Rider's Paradise

Transit Score ®

100/100

Biker's Paradise

Bike Score ®

Overview

Daily errands do not require a car. World-class public transportation. Daily errands can be accomplished on a bike.

Transit Summary

21 nearby routes: 16 bus, 5 rail, 0 other

Walkability averages in the surrounding area

The average walkability score in the surrounding area is Walk Score: 77/100, Transit Score: 77/100, Bike Score: 75/100.

Points of Interest near 29 WINCHESTER STREET, Toronto (Cabbagetown South St. James Town), ON M4X1A6

Frequently Asked Questions for 29 WINCHESTER STREET

Source: Realty.com

29 WINCHESTER STREET, Toronto (Cabbagetown South St. James Town), ON M4X1A6 in Toronto (Cabbagetown-South St. James Town), ON M4X1A6 is a quadruplex listed at $3,400,000. Highlights include 4 bedrooms, 4 bathrooms. Realty.ca has 50 photos, sales history, school insights, and mortgage tools for this listing.

Realty.com has 50 photos of 29 WINCHESTER STREET.

The full address for this home is 29 WINCHESTER STREET, Toronto (Cabbagetown South St. James Town), ON M4X1A6.

29 WINCHESTER STREET has been listed on Realty.com since Fri July 17, 2026

Daily errands do not require a car. World-class public transportation. Daily errands can be accomplished on a bike.

The average walkability score in the surrounding area is Walk Score: 77/100, Transit Score: 77/100, Bike Score: 75/100.

Listing provided courtesy of: ROYAL LEPAGE TERREQUITY SW REALTY
Listing agent: LISA SHIRRIFF

This content last refreshed on 2026-10-02 08:03:16. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.