Proudly Canadian
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 1 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 2 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 3 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 4 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 5 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 6 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 7 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 8 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 9 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 10 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 11 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 12 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 13 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 14 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 15 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 16 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 17 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 18 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 19 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 20 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 21 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 22 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 23 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 24 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 25 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 26 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 27 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 28 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 29 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 30 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 31 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 32 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 33 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 34 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 35 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 36 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 37 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 38 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 39 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 40 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 41 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 42 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 43 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 44 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 45 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 46 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 47 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 48 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 49 of 50
Detached for sale at 161 Winchester Street, Toronto C08 - 2 bedroom, 3 bathroom - Photo 50 of 50
1 / 5047 locked
Active

$1,899,000

161 Winchester St

Toronto C08, ON M4X 1B5

161 Winchester St, Toronto C08Listed at $1,899,000. 2 bedroom, 3 bathroom 2-Storey. MLS® C13171756.

2Beds
3Baths
2500-3000sqft
2-Storey
2Parking
$14,779.05 (2025)

What's this home worth?

Get a free estimate for 161 Winchester St

Description

Rare opportunity to own a truly unique mixed-use corner property in the heart of Cabbagetown, directly across from Riverdale Park and Riverdale Farm. This character-filled property features a functioning main floor corner commercial space currently operating as a well-established ice cream/snack bar, along with two separate and self-contained one-bedroom residential units known as the Loft and the Cottage. The property also offers two private decks and a large backyard, creating exceptional outdoor space rarely found in the city. A landmark location with incredible charm, strong visibility, and income in one of Toronto's most sought-after neighbourhoods. Steps to parks, transit, local shops, and downtown amenities. An exceptional opportunity for investors, end users, or those seeking a unique live/work property. Parking Currently Not In Use.

Property Details

Property TypeDetached
Style2-Storey
CommunityCabbagetown-South St. James Town
Rooms9+1
Kitchens3
Washrooms3
Square Feet2500-3000 sqft
Lot Dimensions28.29 × 80 ft
Fronting OnSouth
Dir/Cross StSumach St/ Winchester St
ViewPark/Greenbelt
Garage TypeNone
DrivePrivate
Parking Drive Spaces2
Total Parking Spaces2
ExteriorBrick, Board & Batten
RoofAsphalt Shingle
FoundationUnknown
BasementPartial Basement
Heating TypeForced Air
Heating SourceGas
A/COther
SewersSewer
Taxes (2025)$14,779.05
HSTIncluded In
Listed Date5/25/2026
Days on Market12 days
PossessionTBA

Virtual Tour

Powered by YouTube

Vick Yogeswaran - REALTOR

Your agent: Vick Yogeswaran

REALTOR® · RE/MAX Realtron Realty Inc.

Same-day showings available
WhatsApp Us About This Listing

Property Insights

Home Value
Estimate

Listing Courtesy of: SOTHEBY'S INTERNATIONAL REALTY CANADA

MLS® #C13171756

TRREBMLS®

The listing data is provided under copyright by the Toronto Regional Real Estate Board (TRREB). The listing data is deemed reliable but is not guaranteed accurate by TRREB. The trademarks REALTOR®, REALTORS®, and the REALTOR® logo are controlled by The Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by CREA and identify the quality of services provided by real estate professionals who are members of CREA. Used under license.

© 2026 Toronto Regional Real Estate Board. All rights reserved.

Thinking about living in Toronto?

Explore the neighbourhood guide for Toronto — market trends, popular areas, buyer tips, and more.

HouseIndex Take: 161 Winchester Street

This detached (2-Storey) is located in the Cabbagetown-South St. James Town neighbourhood of Toronto.

The home offers 2 bedrooms, 3 bathrooms.

Features include a partial basement basement, 2 parking spaces.

Additional details: lot dimensions of 28.29 × 80 feet.

Listed at $1,899,000 CAD with annual property taxes of $14,779.05 (2025). This listing has been on the market for 12 days.

About Toronto Real Estate

This Detached is located in the Cabbagetown-South St. James Town community in Toronto. Toronto is Canada's largest city and the economic hub of the Greater Toronto Area. With world-class transit, diverse neighbourhoods from the Annex to Scarborough, and proximity to major employers in the Financial District, it remains the most sought-after real estate market in Ontario. Buyers benefit from extensive GO Transit and TTC subway connectivity. Detached homes in Toronto are in high demand among families seeking space, privacy, and long-term equity growth.

TTC subway & streetcar networkWorld-class dining & entertainmentUniversity of Toronto & major hospitals nearbyWaterfront trails & ravine parks
Walkability: Highly walkable — many neighbourhoods score 80+ on Walk Score
View full Toronto neighbourhood guide →