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.
2 bedrooms, 2 bathrooms, about 2,500 sq ft, works out to roughly $700 per square foot, the bed-to-bath ratio is generous. Chat with Zara if you'd like a deeper read on whether this detached fits your budget and timing.
Inside 161 Winchester St
Every detail from the listing, in one place.
Type
Detached
Style
2-Storey
Living space
2500-3000 sq ftas stated on the listing
Parking
2 spaces
Basement
Partial Basement
Features & systems
Parking & garage
Parking spaces
2
Interior
Basement
Partial Basement
Lot & land
Lot size (sqft)
0
Listing & possession
Property style
2-Storey
Property class
Detached
161 Winchester St Price & Sale History
Earlier listings of this property, list-price changes, and the most recent annual property tax on the listing.
Independent mortgage broker · OAC · rates subject to change and underwritingMortgage Squad →
Referral disclosure: Summitly may refer you to Mortgage Squad Advisors, an affiliated mortgage partner. You are free to choose any lender or mortgage professional.
Monthly cost
Enter a rate to see the monthly cost
An estimate, not a quote. Utilities and insurance are extra.
Affordability calculator
Estimated monthly payment
$8,597
/mo
based on the purchase price of $1,749,900
$349,980 cash
$1,399,920 financed
$1,179,100 total interest
Principal54%$1,399,920
Interest46%$1,179,100
20% down · 25-yr amortization · 5.50% rate. Principal & interest only — taxes, condo fees, and insurance not included.
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Figures are Summitly estimates for illustration only — not from TRREB or the MLS® feed, and not a mortgage approval, appraisal, or financial advice.
Rental income potential
Est. monthly rent
low–high
Gross yield
rent × 12 ÷ price
Cap rate (est.)
net of tax + fees
Summitly AI estimate for discussion only — not from TRREB or the MLS® feed, and not an appraisal or investment advice. Yield and cap rate are derived from the estimated rent versus the asking price.
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Mortgage financing is arranged through Mortgage Squad Advisors. Summitly is the technology platform that powers this site. Estimated values, AI insights, calculator results, and rental projections shown on this page are generated by Summitly and are not provided by, reviewed by, or sourced from TRREB, the MLS®, or the listing brokerage; they are not appraisals or opinions of value. 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 Coldwell Banker® name and logo are trademarks of Coldwell Banker Real Estate LLC.
Similar homes for sale nearby in Toronto
Other 3–4 bed homes for sale in Toronto around $1.7M.
Average days on market31Homes sold in about 31 days on average.
Sale-to-list ratio5041.4%On average, homes sold at or above asking.
Active listings13,703Homes for sale here right now.
Median vs prior 90 days+2.8%Compared with Apr 18 – Jul 17, 2026: prices up.
Based on 9,408 sales from Jul 17 – Oct 15, 2026 (6,681 in the prior 90 days). Aggregate MLS® figures for closed sales; individual sold prices are shown only to signed-in members.
161 Winchester St is listed at $1,749,900 (MLS® C13171756). Summitly updates the price as soon as the MLS® record changes.
Is $1,749,900 a good price for 161 Winchester St?
Summitly rates it Excellent Deal: the asking price is 10% or more below Zara's estimate, an estimate built from recent sales in Toronto. The rating is an automated opinion, not an appraisal; "What's it worth?" on this page shows how it is worked out. See Zara's estimate
Has the price of 161 Winchester St changed?
Yes — it was first listed at $1,999,000 and is now $1,749,900, a drop of $249,100 (12.5%).
How many bedrooms and bathrooms does 161 Winchester St have?
161 Winchester St has 2 bedrooms and 2 bathrooms, with about 2,500–3,000 square feet of living space. It is a detached home in Toronto.
Is 161 Winchester St close to transit?
The nearest rapid-transit station is Castle Frank Station (Line 2), about 870 m (about a 11-minute walk) in a straight line. Broadview Station is about 1.2 km (about a 15-minute walk), and Sherbourne Station is about 1.2 km (about a 15-minute walk). Distances are straight-line, not walking routes; check the transit agency for routes and schedules.
How much would the monthly mortgage be on 161 Winchester St?
About $8,597 a month — principal and interest on $1,749,900 with 20% down ($349,980), a 25-year amortization and an assumed 5.5% interest rate. The mortgage calculator on this page lets you change the down payment, amortization and rate.
How does 161 Winchester St compare with other homes in Toronto?
Its asking price of $1,749,900 is about 106% above the median sold price in Toronto over the last 90 days, $848,884, across 9,408 closed sales on the TRREB MLS®. A city median mixes every type and size of home, so the comparable sales on this page are the closer guide.
Has 161 Winchester St been sold before?
Summitly has no earlier MLS® sale or lease of 161 Winchester St on record from the last two years. Older records aren't shown under TRREB rules.
Where is 161 Winchester St?
161 Winchester St is in Toronto, ON. Schools, transit, parks and shops nearby are under Location & lifestyle on this page.
How long has 161 Winchester St been on the market?
143 days — 161 Winchester St was listed on May 25, 2026.
What is the price per square foot of 161 Winchester St?
About $583 to $700 per square foot: the asking price of $1,749,900 over the 2,500–3,000 sq ft the listing gives as its size range.
