MLS® listing
229 Winona Drive: detached house for sale
$1,569,000
From the listing brokerage
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!
Facts on the listing
| Square feet | 2000-2500 |
|---|---|
| Style | 2-Storey |
| Basement | Finished with Walk-Out |
| Lot width | 33 |
| Lot depth | 100 |
| Lot measured in | Feet |
| Faces | East |
| Parking spaces | 2 |
| Garage | Detached |
| Heating | Radiant |
| Cooling | Wall Unit(s) |
| Kitchens | 3 |
| Property tax | $6,637 |
| Tax year | 2026 |
| Interior features | None |
Listing courtesy of ROYAL LEPAGE SUPREME REALTY. MLS® C13757114.
About this detached house
229 Winona Drive is a 7 bedroom detached house in TRREB's Oakwood Village community in Toronto, listed for sale at $1,569,000. The listing shows 3 bathrooms and 2000-2500 square feet. The style is given as 2-storey. The lot is listed as 33 by 100 feet. The listing gives the basement as finished with walk-out. It comes with 2 parking spaces and a detached garage according to the listing. The nearest main intersection given is St.Clair and Winona.
These details come from the listing brokerage through TRREB's MLS® System. Room sizes, the lot, the taxes and what is included in the sale should all be confirmed before an offer is firm.
What it costs to buy 229 Winona Drive
At the asking price of $1,569,000, a buyer pays two land transfer taxes on closing: the Ontario tax and the City of Toronto's municipal tax. Both apply to every home inside the City.
| Asking price | $1,569,000 |
|---|---|
| Ontario land transfer tax | $27,855 |
| Toronto municipal land transfer tax | $27,855 |
| Both taxes | $55,710 |
| First-time buyer relief, if you qualify | up to $8,475 |
| Minimum down payment | $313,800 |
The down payment figure is the federal minimum: 20 percent, because a home at $1.5 million or more cannot carry mortgage default insurance. A lender can ask for more. These figures use the asking price, so they change if you pay more or less. Legal fees, title insurance and adjustments are extra: ask your lawyer for a written quote. This is general information, not legal or tax advice. Confirm the figures with a lawyer or accountant. You can change the price in our land transfer tax calculator and our mortgage calculator.
What it costs to own each month
| Property tax (2026) | $6,637 a year, about $553 a month |
|---|
That is before a mortgage payment, home insurance and utilities. The listing shows no monthly maintenance fee, so upkeep of the building and the lot is the owner's own cost.
How the asking price compares
TRREB recorded 550 detached house sales in the City of Toronto in August 2026, at a median price of $1,170,000 and an average of $1,525,749. This home is listed at $1,569,000, which is $399,000 above that median.
The median covers every neighbourhood, size and condition in the City of Toronto, so it is a reference point and not a valuation of this home. Location, size, lot, parking and condition all move the price. Our Toronto house prices page has the figures for every home type.
What to check before you make an offer
- Book a home inspection. An inspector looks at the roof, foundation, wiring, plumbing and heating. The listing gives the heating as radiant.
- Have a lawyer search the title. A title search shows mortgages, liens and easements registered against the property. Ask whether a survey exists and whether it matches the lot on the listing, 33 by 100 feet.
- Ask about permits. Ask which renovations had building permits and whether those permits were closed. The listing shows 3 kitchens. If there is a second unit, ask whether it meets the municipality's rules for one.
- Confirm what is included. Appliances, light fixtures and window coverings are included only if the agreement says so. Ask whether the water heater or furnace is rented.
- Get your financing in writing. A lender looks at the property tax and heating costs as well as the price.
- See it in person. The listing has a virtual tour, but photos do not show noise, light at different hours or the state of the street and the homes beside it.
Our first-time home buyer guide and our page for buyers walk through each step. This is general information, not legal advice. Confirm the details with a lawyer.
Toronto neighbourhoods and prices
Our neighbourhood guides set out TRREB prices by home type, transit and the housing in each area we cover.
Toronto neighbourhood guides · Toronto house prices · All Toronto homes for sale
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Questions about 229 Winona Drive
How much is land transfer tax on 229 Winona Drive?
At the asking price of $1,569,000 the Ontario tax is $27,855 and the Toronto tax is $27,855, $55,710 in total. A first-time buyer who qualifies can get up to $8,475 back. Confirm the final figures with your lawyer.
What is the minimum down payment for 229 Winona Drive?
$313,800 at the asking price of $1,569,000, under the federal minimum down payment rules. A lender may require more.
How much is the property tax on 229 Winona Drive?
The listing shows $6,637 a year for 2026, about $553 a month.
Is 229 Winona Drive priced above or below the median?
It is listed at $1,569,000. The August 2026 median for detached house sales in the City of Toronto was $1,170,000 across 550 sales, so the asking price is $399,000 higher. The median covers all sizes and neighbourhoods.
How do I book a showing for 229 Winona Drive?
Use the form on this page or call us. Quote MLS® C13757114. We will confirm the listing is still available and arrange a time with the listing brokerage.
Is 229 Winona Drive still for sale?
This page is refreshed from TRREB's MLS® System through the day. If the listing sells or is withdrawn the page says so. Contact us to confirm before you make plans.
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