229 Winona Dr is a 6-bedroom, 3-bathroom detached home in Toronto, listed for $1,569,000. It has 2000-2500 sq ft of living space.
1Attention Investors and End-Users!
2A high-potential property has arrived just north of the vibrant crossroads of St.
3Complete with on site parking for two vehicles total and a garage for parking for one of those 2 vehicles and\or extra storage, the property is exceptionally accessible with the TTC just steps away.
Attention Investors and End-Users! A high-potential property has arrived just north of the vibrant crossroads of St. Clair Avenue West and Winona Drive. Nestled in a quiet, coveted, and family-friendly neighbourhood where Humewood, Hillcrest, Oakwood Village, and Wychwood meet, this versatile detached home offers an amazing opportunity to make it your own, providing the ultimate canvas for a spectacular single-family home transformation.This bright, spacious, and updated home features 6 bedrooms, 3 bathrooms, and 3 kitchens. Complete with on site parking for two vehicles total and a garage for parking for one of those 2 vehicles and\or extra storage, the property is exceptionally accessible with the TTC just steps away. Enjoy a quick commute to both St. Clair subway stations via the streetcar, with cafes, bars, restaurants, and vibrant city life all within walking distance. With a Walk Score of 95, you do not want to miss this opportunity-act now!
6 bedrooms, 3 bathrooms, about 2,000 sq ft, works out to roughly $785 per square foot. Chat with Zara if you'd like a deeper read on whether this detached fits your budget and timing.
Inside 229 Winona Dr
Every detail from the listing, in one place.
Type
Detached
Style
2-Storey
Living space
2000-2500 sq ftas stated on the listing
Parking
2 spacesYes garage
Basement
Finished with Walk-Out
Features & systems
Parking & garage
Garage
Yes
Parking spaces
2
Interior
Basement
Finished with Walk-Out
Lot & land
Lot size (sqft)
0
Listing & possession
Property style
2-Storey
Property class
Detached
229 Winona Dr Price & Sale History
Earlier listings of this property, list-price changes, and the most recent annual property tax on the listing.
For saleListedThis listingMLS® C13757114$1,569,000
Sourced from MLS®. Includes earlier listings of this property on record.
What's it worth?
How 229 Winona Dr Compares to the Toronto Market
Zara compares it with recent sales of similar homes nearby. It's a guide, not an appraisal.
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
$7,708
/mo
based on the purchase price of $1,569,000
$313,800 cash
$1,255,200 financed
$1,057,208 total interest
Principal54%$1,255,200
Interest46%$1,057,208
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 5–8 bed homes for sale in Toronto around $1.6M.
Average days on market31Homes sold in about 31 days on average.
Sale-to-list ratio4987.8%On average, homes sold at or above asking.
Active listings12,139Homes for sale here right now.
Median vs prior 90 days0.0%Compared with Apr 29 – Jul 28, 2026.
Based on 9,511 sales from Jul 28 – Oct 26, 2026 (6,903 in the prior 90 days). Aggregate MLS® figures for closed sales; individual sold prices are shown only to signed-in members.
229 Winona Dr is listed at $1,569,000 (MLS® C13757114). Summitly updates the price as soon as the MLS® record changes.
Is $1,569,000 a good price for 229 Winona Dr?
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 229 Winona Dr changed?
No — 229 Winona Dr is still listed at its original asking price of $1,569,000.
How many bedrooms and bathrooms does 229 Winona Dr have?
229 Winona Dr has 6 bedrooms and 3 bathrooms, with about 2,000–2,500 square feet of living space. It is a detached home in Toronto.
Is 229 Winona Dr close to transit?
The nearest rapid-transit station is St. Clair West Station (Line 1), about 1.5 km (about a 18-minute walk) in a straight line. Oakwood Station is about 1.9 km (about a 24-minute walk), and Cedarvale Station is about 2.0 km (about a 25-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 229 Winona Dr?
About $7,708 a month — principal and interest on $1,569,000 with 20% down ($313,800), 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 229 Winona Dr compare with other homes in Toronto?
Its asking price of $1,569,000 is about 87% above the median sold price in Toronto over the last 90 days, $840,000, across 9,511 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 229 Winona Dr been sold before?
Summitly has no earlier MLS® sale or lease of 229 Winona Dr on record from the last two years. Older records aren't shown under TRREB rules.
Where is 229 Winona Dr?
229 Winona Dr is in Toronto, ON. Schools, transit, parks and shops nearby are under Location & lifestyle on this page.
How long has 229 Winona Dr been on the market?
48 days — 229 Winona Dr was listed on September 8, 2026.
What is the price per square foot of 229 Winona Dr?
About $628 to $785 per square foot: the asking price of $1,569,000 over the 2,000–2,500 sq ft the listing gives as its size range.
Does 229 Winona Dr have parking or a garage?
Yes — the listing gives 2 parking spaces. Garage: Yes.
