161 Winchester Street, Toronto, ON
Cabbagetown-South St. James Town, Toronto · MLS® C13171756
About this home
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.
Key facts
- Property type
- Detached, 2-Storey
- MLS®
- C13171756
- Bedrooms
- 2
- Bathrooms
- 3 (1 half)
- Size
- 2500-3000
- Lot
- 28.29 × 80 ft
- Cross streets
- Sumach St/ Winchester St
- Parking
- 2 parking
- Driveway
- Private
- Basement
- Partial Basement
- Heating
- Forced Air
- A/C
- Other
- Exterior
- Brick, Board & Batten
- Foundation
- Unknown
- Roof
- Asphalt Shingle
- Sewer
- Sewer
- Property tax
- $14,779 / 2025
- Days on market
- 53
- Listing brokerage
- SOTHEBY'S INTERNATIONAL REALTY CANADA
Listing history
- May 25, 2026Listed$1,899,000
Price and status history from the listing board. Deemed reliable but not guaranteed.
Listed at $1,899,000, this home is tracking about 25% below a wider set of listings, though close matches were thin, so it is worth confirming with a precise CMA rather than reading it as a clear deal. The number above is my independent estimate of value, not the asking price.
There are only a few closely comparable homes right here, so this is a broad read from wider listings in the area. Ask me for a precise CMA before relying on it.
Based on 21 similar homes nearby, adjusted for size, beds, and baths.Median of 21 comparable active listings, adjusted for size, beds, and baths. The city (MPAC) assessment points to about $3.11M, higher than the comparables and worth a second look.
How I got there
Here is the exact math behind the estimate. I start from the closest comparable listing and adjust for the real differences (size, beds, baths) to land on a like-for-like value for this home.
- Closest comparable, listed at $1.87M
- Size difference +$932K
- Bedrooms −$30K
- Bathrooms −$15K
- Adjusts to $2.76M
That comparable adjusts to $2.76M; the $2.55M estimate above is the median of all 21 comparables, which is steadier than any single home.This uses comparable active listings, not sold prices. Lot, condition, and finishes are my in-person call, and I can run a full CMA with recent solds.
The assigned public school is Sprucecourt Public School. EQAO is only one input, and families here also look at French Immersion, boundary, and private options, the full breakdown is below.
On location, this is a very walkable address with everyday errands close by. Gerrard St East at Sumach St is about a 5-minute walk away. Walkable, transit-friendly spots tend to hold value and widen your resale pool.
Total price vs nearby homes. Fair value about $2.55M, median of 21 comparables.
What the listing highlightsThese are claims from the listing. The only way to know for sure is to see it in person, and I am happy to book you a private showing.
- Transit / schools nearby: convenience and resale support, verify the exact distances and school catchment.
- Value driver
This home lists 32% below the area average of $1,010/sqft.
52 days longer than the Toronto average (1 days).
View comparable listingsPrice per square foot vs the area average.
Neighbourhood & location
Cabbagetown-South St. James Town, Toronto, ON
Enter a workplace or destination and we’ll show the door-to-door time by car, transit and bike.
Getting around
Very WalkableA walkability read built from the amenities around this home: how close the nearest transit stop is, and how many grocery, dining, park, and pharmacy destinations fall within a 15-minute walk. It is a guide, not a guarantee. Places data from Google.
Most daily errands can be done on foot.
🚉 Nearest transit: Gerrard St East at Sumach St, about 434 m away
Within a 15-minute (1.5 km) walk.
How asking prices compare in the closest areas to this home. Longer bars mean a pricier market.
Typical asking price of active listings of the same type, per area (outliers removed). Toronto.
Get the full neighbourhood report (schools, parks, transit & safety) →
The public and Catholic schools this address is zoned for, with EQAO results (the share of students meeting Ontario's provincial standard).
School attendance boundaries and EQAO results are Ontario government data and can change. Confirm the current catchment with the school board before relying on it.
Affordability & Mortgage
Income needed assumes a ~32% GDS ratio; weekly is mortgage principal & interest only. Price ÷ income is the home price over the income needed. Fixed reference assumptions so listings compare on equal footing, not a lending decision.
Calculate and customize your mortgage and other expenses
Adjust the down payment, rate, and amortization, and add property tax, condo fees, and heating to see your true monthly cost.
Your numbers
Homes over $1.5M can't be insured, so 20% down or more is required.
Conventional (20%+ down). Best insured 5-year fixed 3.99% via Ratehub.ca (as of July 17, 2026); conventional rates run a little higher.
Mortgage amount $1,519,200 · 4.14% over 25 years
Total monthly cost
- Mortgage payment (monthly equivalent)
- $8,107
- Property tax
- $1,232
- Condo / maintenance fees
- $0
- Heating
- $0
- Estimated monthly cost
- $9,339
Add your own property tax, condo fees, and heating on the left for a sharper total.
One-time closing costs
- Ontario land transfer tax
- $34,455
- Toronto municipal land transfer tax
- $34,455
- Estimated closing costs
- $68,910
Plus your down payment of $379,800. Legal fees, title insurance, and adjustments are extra and vary by deal.
Mortgage stress test
Lenders qualify you at the greater of your rate plus 2% or 5.25%. You do not pay this rate. It just shows you could still handle payments if rates rose, so aim to stay comfortable at this higher number.
Over the full 25 years
At the end of your 5-year term
- Total paid over the term
- $486,421
- Principal paid down
- $193,470
- Interest paid
- $292,950
- Balance remaining
- $1,325,730
Talk to Team Asgarian about your options
Rates and programs change often. We will connect you with a trusted mortgage professional and build a plan that fits your budget and goals.
Estimates only, not a mortgage quote or pre-approval. Figures use Canadian semi-annual compounding, current minimum down-payment rules, CMHC premium tiers, and Ontario (plus Toronto, when selected) land transfer tax. Actual rates, taxes, insurance, and closing costs vary by lender and property. Confirm every number with your mortgage professional.
Investor snapshot
Thinking of this home as an investment? We will pull real comparable rents and run the full numbers with you.
Talk about the numbersEstimates only. Rent is modelled on above-grade size and local norms, so a finished basement or second suite (a separate entrance often means one) can push real rent well above this. Taxes, fees, and vacancy vary by property, and cap rate is before financing. A starting point, not a final number, let us run the real ones with you.
Helpful resources
All information deemed reliable but not guaranteed. For personal, non-commercial use only. Listing courtesy of SOTHEBY'S INTERNATIONAL REALTY CANADA. MLS®/PropTx.