464-468 Winona Drive, Toronto, ON
Oakwood Village, Toronto · MLS® C12554262
About this home
An exceptionally rare opportunity to acquire a premier development site in the heart of Midtown Toronto between Humewood and Cedarvale neighborhoods -one of the city's strongest and most resilient rental markets. The listing price includes Site Plan Approval (SPA) for the proposed 200-unit, 11-story rental development. PAC meetings' feedback and prepared Application Package suggest a short approval period. All seller's obligations related to SPA delivery will be detailed in the Agreement of Purchase and Sale. Offers may be made conditional on these final approvals, giving developers valuable certainty as the project moves toward completion of the planning process. Two independent appraisals have valued the land at about $25 million without approvals, reflecting its true highest and best use as a large-scale rental development. The proposed building aligns perfectly with CMHC's MLI Select program. The completed asset is expected to exceed $100 million in value with projected annual rental income of more than $5,500,000.Situated in a prime Midtown location surrounded by established high-demand rental buildings, the site benefits from strong municipal support for rental intensification as Toronto prioritizes new rental supply. The previously approved townhouse plan is no longer the highest and best use of the land, which is now optimized for a transformative multi-residential project. With near-zero vacancy in the area and robust demand for high-quality rental housing, this is a rare chance for forward-thinking developers to deliver a flagship rental asset in one of Toronto's most coveted neighbourhoods.
Key facts
- Property type
- Other, Other
- MLS®
- C12554262
- Lot
- 71 × 303 ft
- Cross streets
- St. Clair and Winona
- Sewer
- Sewer
- Property tax
- $16,500 / 2025
- Days on market
- 241
- Listing brokerage
- FOREST HILL REAL ESTATE INC.
Heads up: the asking price here sits well above what comparable listings suggest. That can point to premium finishes, a bigger lot, or simply an ambitious ask, so it is worth a close look before you offer. I would not put an automatic figure on this one. Tell me you are interested and I will pull the most comparable recent sales and give you a straight answer on what it will really take.
Ask Moe if this price is fairThe assigned public school is J R Wilcox Community 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. Vaughan Rd at Winona Dr East Side is about a 1-minute walk away. Walkable, transit-friendly spots tend to hold value and widen your resale pool.
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.
- Development potential: upside only if zoning permits, verify with the city before relying on it.
- Worth verifying
The closest active listings by size, beds, and price, so you can see what this home is up against.
The 5 closest of 8 active listings nearby.
See all comparable homesNot enough sq ft data to place this home on the area price curve.
Neighbourhood & location
Oakwood Village, Toronto, ON
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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: Vaughan Rd at Winona Dr East Side, about 43 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 $23,599,200 · 4.14% over 25 years
Total monthly cost
- Mortgage payment (monthly equivalent)
- $125,934
- Property tax
- $1,375
- Condo / maintenance fees
- $0
- Heating
- $0
- Estimated monthly cost
- $127,309
Add your own property tax, condo fees, and heating on the left for a sharper total.
One-time closing costs
- Ontario land transfer tax
- $723,950
- Toronto municipal land transfer tax
- $1,778,900
- Estimated closing costs
- $2,502,850
Plus your down payment of $5,899,800. 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
- $7,556,045
- Principal paid down
- $3,005,364
- Interest paid
- $4,550,682
- Balance remaining
- $20,593,836
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 FOREST HILL REAL ESTATE INC.. MLS®/PropTx.