$1,999,000
161 Winchester Street, Toronto C08, ON M4X 1B5
Beds
Baths
Parking
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 Summary

Property Type Commercial
Property Sub Type Commercial Retail
Transaction Type For Sale
Possession TBA

Building

Building Type Commercial Retail
Square Footage 2856
Building Area Units Square Feet
Heating Gas Forced Air Open
Cooling Yes

Measurements

Lot Size 28.29 x 80
Lot Size Units Feet
Frontage 28.29
Depth 80
Total Living Area 2856

Land

Address 161 Winchester Street, Toronto C08, ON M4X 1B5
City Toronto C08
Community Cabbagetown-South St. James Town
County / Area Toronto
Cross Street Sumach St/ Winchester St
Parcel Number 210840368

Parking and Garage

Garage Type None

Taxes and Listing Info

List Price $1,999,000
Annual Taxes $14,779
Tax Year 2025
Status Active
Listing Date 2026-05-25T19:55:26Z
Updated 2026-05-25T19:55:26Z
MLS Number C13171750
Local Market Insight

What Buyers Should Know About 161 Winchester Street, Toronto C08, ON M4X 1B5

This editorial summary helps buyers look beyond the headline price and review the neighbourhood, transit, schools, rental demand, long-term value, and due-diligence items that often matter before booking a showing or submitting an offer.

Neighbourhood Analysis

161 Winchester Street, Toronto C08, ON M4X 1B5 is positioned in Cabbagetown-South St. James Town, a part of Toronto C08 where buyers should compare the street setting, nearby amenities, daily travel routes, and surrounding housing stock. For a Commercial Retail, the strongest fit often depends on whether the location supports everyday routine as well as the numbers on paper.

School And Family Considerations

Families reviewing this Commercial Retail should confirm school boundaries directly with the local school boards before relying on listing notes. It is also worth checking walkability to parks, childcare, recreation centres, libraries, and community facilities because these details can influence both lifestyle value and future resale demand.

Transit And Access

The location should be assessed around commute patterns, access to Sumach St/ Winchester St, public transit options, parking availability, and drive times to employment areas. A property with available parking and practical road access can appeal to buyers who need convenience without giving up neighbourhood quality.

Investment Potential

At $1,999,000, buyers should compare recent nearby sales, days on market, condition, lot utility, and the cost of future repairs or upgrades. The property shows available bedrooms, available bathrooms, basement details marked as to be confirmed, and a lot size of 28.29 x 80, all of which can affect value.

Rental Demand

If this property is being reviewed as a rental or investment, demand should be measured by bedroom count, transit access, employment access, nearby schools, parking, and the condition of the unit or home. In Toronto C08, rental appeal usually improves when a property is easy to maintain and simple for tenants to live in.

Local Attractions And Amenities

Buyers should look at grocery access, restaurants, trails, parks, shopping, medical services, and weekend amenities around Cabbagetown-South St. James Town. These features do not always appear in the MLS data, but they can make a major difference in how the home feels after move-in and how future buyers compare it.

Builder, Condition, And Due Diligence

For resale homes, review renovations, permits, roof and mechanical age, exterior condition, inclusions, and rental items. For condo or newer properties, review building history, maintenance fees, reserve fund information, rules, amenities, and future cost exposure. A showing and document review should confirm anything not visible in the listing.

Nearby Infrastructure

Infrastructure matters because transit improvements, road projects, schools, parks, commercial growth, and employment nodes can change how an area performs over time. For 161 Winchester Street, Toronto C08, ON M4X 1B5, buyers should check municipal plans, nearby construction, zoning context, and future projects that may affect enjoyment or resale value.

This section is informational only. Buyers should verify schools, measurements, rental rules, taxes, zoning, and property condition with the appropriate professionals before making a decision.

Listing data is provided through PropTx/MLS data services and is deemed reliable but not guaranteed. Listings are subject to change without notice.