229 Winona Drive, Toronto, ON
Oakwood Village, Toronto · MLS® C13757114
About this home
In short
- Attention Investors and End-Users.
- 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 andor extra storage, the property is exceptionally...
- With a Walk Score of 95, you do not want to miss this opportunity-act now.
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 andor 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!
Key facts
- Property type
- Detached, 2-Storey
- MLS®
- C13757114
- Bedrooms
- 6+1 (7 total)
- Bathrooms
- 3
- Size
- 2000-2500 sq ft
- Lot
- 33 × 100 ft
- Cross streets
- St.Clair and Winona
- Parking
- 1 garage · 2 parking (detached)
- Basement
- Finished with Walk-Out
- Kitchens
- 3 (2 + 1)
- Heating
- Radiant
- A/C
- Wall Unit(s)
- Exterior
- Brick
- Foundation
- Unknown
- Roof
- Shingles
- Sewer
- Sewer
- Property tax
- $6,637 / 2026
- Days on market
- 41
- Listing brokerage
- ROYAL LEPAGE SUPREME REALTY
Rooms
w/o to yard · tile floor
window · tile floor
window · east view · tile floor
Concrete Floor
window · tile floor
window · closet
window · laminate
Concrete Floor
window · tile floor
laminate · window
window · linen closet · overlooks living
window · laminate
Glass Block Window
window · west view · overlooks dining
window · laminate
window · laminate
window · tile floor
window · laminate
No automatic estimate is shown here: there is not a deep enough record of recent sales of homes like this one in this neighbourhood to support one.
Considering this property? Request a written price readThe assigned public school is Humewood Community School. EQAO is only one input, and families here also look at French Immersion, boundary, and private options, the full breakdown is below.
For sale
For sale
For sale
For sale
For sale
For sale
For sale
For saleNothing closely matching this home is listed nearby right now, so these are the nearest detached listings on the market.
Per square foot, these ask about $1,154/sqft; this home lists at $697/sqft. Size is part of the price story, not just the sticker.
The 5 closest of 8 active listings nearby.
See all comparable homesSold price trend
Median sold price for detached homes in Oakwood Village: $1.12M in September 2026, up 9% from a year ago, on 97 closings in 11 months.
Line: median sold price, each month averaged with its neighbours and weighted by closings. Bars: closings that month.
Month by month
| Month | Median sold | Closings |
|---|---|---|
| October 2025 | $913K | 10 |
| November 2025 | $1.07M | 9 |
| January 2026 | $1.20M | 9 |
| February 2026 | $1.18M | 6 |
| March 2026 | $1.35M | 8 |
| April 2026 | $1.41M | 10 |
| May 2026 | $1.28M | 9 |
| June 2026 | $1.13M | 11 |
| July 2026 | $1.10M | 9 |
| August 2026 | $1.24M | 8 |
| September 2026 | $1.12M | 8 |
Neighbourhood & location
Oakwood Village, Toronto, ON
Enter a workplace or destination and we’ll show the door-to-door time by car, transit and bike.
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.
Also nearby: 12 more schools within 2.5 km
Not the assigned catchment: schools a family here could reach, with EQAO results where published.
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 4.34% via Ratehub.ca (as of October 20, 2026); conventional rates run a little higher.
Mortgage amount $1,255,200 · 4.49% over 25 years
Total monthly cost
- Mortgage payment (monthly equivalent)
- $6,940
- Property tax
- $553
- Condo / maintenance fees
- $0
- Heating
- $0
- Estimated monthly cost
- $7,493
Add your own property tax, condo fees, and heating on the left for a sharper total.
One-time closing costs
- Ontario land transfer tax
- $27,855
- Toronto municipal land transfer tax
- $27,855
- Estimated closing costs
- $55,710
Plus your down payment of $313,800. 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
- $416,413
- Principal paid down
- $153,362
- Interest paid
- $263,051
- Balance remaining
- $1,101,838
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
Income potential: the basement has a separate entrance, which often supports a rentable in-law or second suite. That can lift real rent well above the figure above and help carry the mortgage. Ask us about permitted use in this area.
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 ROYAL LEPAGE SUPREME REALTY. MLS®/PropTx.