161 Winchester Street, Toronto C08, ON

$1,999,000
MLS#:C13171756
2 beds
3 baths
2500-3000 sqft
2.0 parking
Residential Freehold
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Description

Property Highlights

Welcome to this remarkable ["2-Storey"] detached located in the coveted neighborhood of Cabbagetown-South St. James Town. Expertly crafted featuring premium brick and board & batten construction, this residence presents an exceptional opportunity offered at $1,999,000 to acquire a beautiful home in a highly sought-after setting. Designed for both comfortable daily living and elegant entertaining, the layout maximizes natural light, functional flow, and lifestyle utility.

  • 2 Bedrooms and 3 Bathrooms with 3 functional kitchens
  • Generous living space spanning 2500-3000 sqft on a premium 28.29 x 80 ft lot
  • Features a ["partial basement"] basement, adding superb versatility for recreation, a home gym, or extra storage
  • 2.0 total parking spaces available
  • Notable attributes: Separate Hydro Meter
  • equipped with ["other"] central cooling and highly efficient forced air heating via gas

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.

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Key Features

Bedrooms
2
Bathrooms
3
Kitchens
3
Living Area
2500-3000 sqft
Property Type
Residential Freehold

Additional Details

StatusActive
Listed Date5/25/2026
Transaction TypeFor Sale

Property Details

Property Sub-TypeDetached
ConstructionBrick, Board & Batten
Lot Size28.29 × 80 Feet
CountyToronto
Annual Tax$14,779.05
Legal DescriptionPT LT 2 PL D9 TORONTO AS IN CA578609; S/T CA578609; CITY OF TORONTO

Parking & Garage

Parking Spaces2.0
Garage Spaces2
Garage TypeNone

Heating & Cooling

Heat SourceGas
Heat TypeForced Air
Cooling["Other"]

Features

Property Features

Fenced Yard, Hospital, Park, Public Transit, School

Community Features

Location

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161 Winchester Street, Toronto C08, ON

City & Neighborhood Guide

Comprehensive neighborhood overview, demographics, and school rankings for Cabbagetown South St James Town, Toronto C08.

Verified Local Data
Population6,202,225
Median Age39.6 Yrs
Ownership65% Owners
Avg Area List Price$850,000

People & Families

Age Distribution

Household Composition

One-person households
25%
Families with children
50%
Couples without children
24%
Other households
0%

Top Ethnic Origins

Chinese11%
English9%
Indian9%
Irish8%

Local Schools Guide

Elementary Schools

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Secondary Schools

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Homes & Housing

Structural Home Types

Tenure (Ownership vs Rental)

Owner-Occupied65%
Rented35%

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Property History

No historical data available for this property.

This could be the first listing for this address.

Pricing & Value Insights

Data-driven valuation for 161 Winchester Street, Toronto C08, ON M4X 1B5

Estimated Sales Range
$1.2M - $1.4M

Based on 0 recent similar sales in the pocket.

Market Speed
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Properties in this area are selling at a steady pace.

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Financial Audit

Estimated Costs

Loan Amount$1,599,200
Monthly Mortgage$9,292
Property Tax (Est.)$1,232
Utilities & Maint.$350
Total Monthly Cost$10,874

Nearby School Rankings

No schools found within 3 km of this property.

Within 2km radiusFraser Institute Ratings

Nearby Listings

Distance:

No current listings found in Toronto C08.

Notice: Market Insights are generated by analyzing real-time data and should be used for informational purposes only. Consult with a licensed professional for exact valuations.

Disclaimer: AI Insights are generated by an automated system and should be used for informational purposes only. While we strive for accuracy using current market data and deep-learning models, these assessments do not constitute professional real estate, legal, or financial advice. All property values, predictions, and scores are estimates. We strongly recommend verifying all property details and conducting independent due diligence with a licensed professional before making any purchase decisions.