464-468 Winona Drive
Oakwood VillageToronto, ONM6C 3T7Near St. Clair and Winona
- 0
- Vacant Land
3 upcoming open houses
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What this listing tells us
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.
Cleaned for readability — original MLS® text was lightly de-abbreviated and decapitalized.
Listing, price, and tax history
Every previous listing of this property, every list-price change, and 5 years of estimated annual property tax — switch tabs to drill in.
| Date | Event | Status | Price | Change | MLS® | View |
|---|---|---|---|---|---|---|
| Mar 24, 2026 | Previously listed | Ter | $8,500,000 | — | C12923744 | View |
| Nov 18, 2025 | ListedCurrent | For sale | $29,499,000 | — | C12554262 | This page |
| Aug 8, 2025 | Previously listed | Ter | $24,800,000 | — | C12334019 | View |
| Jul 7, 2025 | Previously listed | Ter | $6,989,999 | — | C12267150 | View |
| Jul 7, 2025 | Previously listed | Exp | $6,989,999 | — | C12267139 | View |
| Jan 21, 2025 | Previously listed | Ter | $24,800,000 | — | C11934192 | View |
| Sep 17, 2024 | Previously listed | Ter | $29,500,000 | — | C9353710 | View |
| Sep 4, 2024 | Previously listed | Ter | $29,950,000 | — | C9299634 | View |
| Apr 1, 2024 | Previously listed | Ter | $6,999,999 | — | C8187644 | View |
| Jan 11, 2024 | Previously listed | Ter | $24,990,000 | — | C7401202 | View |
Inside this property
Systems, finishes, room dimensions, and building information — pulled from the full MLS® feed.
Features & systems
Heating, cooling, parking, exterior, lot, possession, and more.
Systems
2- Water source
- Municipal
- Sewer
- Sewer
Getting around, schools & the block
Walkability and transit, the nearest schools, an interactive map of the exact spot, and what's nearby.
Points of interest classified by the MLS® feed.
- Park
- Public Transit
- School
- School Bus Route
The money — monthly cost, mortgage & return
Everything financial in one place: what you'd pay each month, a live mortgage calculator at the asking price, and what it could return as a rental.
Cost of ownership
A monthly snapshot at typical assumptions — personalize the mortgage just below.
How this home sits in the Toronto market
Live neighbourhood stats, the closed sales you'd negotiate against, and comparable active listings.
The Toronto market right now
Average sold price, days on market, and closed-transaction count for Toronto — sourced from MLS®.
- Avg sold price$1,088,463Last 30 days
- Median sold price$858,962Middle of the market
- Days on market28 dAvg from list to close
- Closed last 30d6,676MLS® transactions
We'll get you into 464-468 Winona Drive — the seller pays our commission
On every MLS® listing in Canada, the seller's brokerage pays a cooperating commission to whoever brings the buyer. Buyer representation is free to you.
$0 to you. The seller pays our fee.
On every MLS® listing in Canada, the seller's brokerage advertises a cooperating commission for the buyer's agent. A Coldwell Banker Summit Realty agent represents you — you owe us nothing.
Property flags & disclosures
An automated scan of public records and news for anything a buyer should know about this specific address — liens, outstanding work orders, or stigma-related history. We never invent flags.
We scanned public records and news for liens, outstanding work orders, and stigma-related history (e.g. a former grow-op or fire) at 464-468 Winona Drive and found nothing flagged. We re-check automatically as new records publish.
Common questions about this property
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How much is 464-468 Winona Drive listed for?
464-468 Winona Drive is listed at $29,499,000 on the MLS® (listing C12554262). The price refreshes on Summitly within minutes of any MLS® change.
How many bedrooms, bathrooms, and square feet does 464-468 Winona Drive have?
Coldwell Banker Summit Realty is a RECO-licensed Ontario real estate brokerage, independently owned and operated. Mortgage financing is arranged through Mortgage Squad Advisors. Summitly is the technology platform that powers this site. Listing data is sourced from MLS® and is provided for informational purposes only — not guaranteed accurate by the MLS® or its members. 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.






