464-468 Winona Drive, Toronto, ON

$29,499,000
MLS#:C12554262
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0 beds
0 baths
Residential Freehold
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Property no longer active

This property was sold on July 12, 2026. This listing is for reference purposes only. to view the sold price.

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Added:Nov 18, 2025(284 days ago)
Updated:Jul 12, 2026(48 days ago)
Last Checked:22 minutes ago

Property Highlights

Welcome to this remarkable vacant land located in the coveted neighborhood of Oakwood Village. Offering a sublime balance of structural integrity and modern aesthetic appeal, this residence presents an exceptional opportunity offered at $29,499,000 to acquire a beautiful home in a highly sought-after setting. Designed for both comfortable daily living and elegant entertaining, the layout maximizes natural light, functional flow, and lifestyle utility.

  • 0 Bedrooms and 0 Bathrooms
  • Premium 71 x 303 ft lot size

Description

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.

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Property Summary

This vacant land located at 464-468 Winona Drive, Toronto is currently for sale and has been available on SousaSells for 284 days. This property is listed at $29,499,000 with an estimated mortgage of $98,191* per month. It has 0 beds, 0 bathrooms, and is unknown square feet. 464-468 Winona Drive, Toronto is in the Oakwood Village neighborhood.

* Estimated mortgage assumes a 30% down payment, 4.00% interest rate, and 30-year amortization.
Is this a Good Home for Families?

Ideal for small families, couples, or individuals seeking a manageable and comfortable living layout in Oakwood Village, Toronto.

Great for Small Household / Couples
What We Love About This Home
  • •Desirable Vacant Land architecture in Oakwood Village, Toronto
Standout Features & Layout
Who Should Buy This Home?

First-time home buyers, professionals, or investors seeking value.

Target Buyer Match

Key Features

000
Property Type
Residential Freehold

Additional Details

StatusSold Conditional
Sold price information is available to members only
AddedNov 18, 2025 (284 days ago)
UpdatedJul 12, 2026 (48 days ago)
Last Checked22 minutes ago
Transaction TypeFor Sale

Property Details

Property Sub-TypeVacant Land
Lot Size71 Ă— 303 Feet
CountyToronto
Annual Tax$16,500
Legal DescriptionPART LOT 20 PL 115 TWP OF YORK PARTS 3 & 4, PLAN 66R26535, TORONTO (YORK) TOGETHER WITH AN EASEMENT OVER PART LOT 20 PL 115 PARTS 1 & 2, 66R26535 AS IN AT5005921 CITY OF TORONTO and PT LT 20 PL 115 TWP OF YORK AS IN CY643901

Parking & Garage

Heating & Cooling

Features

Property Features

  • Park
  • Public Transit
  • School
  • School Bus Route

Interior Features

None listed

Security Features

None listed

Community Features

None listed

Frequently Asked Questions about 464-468 Winona Drive, Toronto, ON

Q.What is the asking price for 464-468 Winona Drive, Toronto, ON ?

The current listing price for 464-468 Winona Drive, Toronto, ON in Oakwood Village, Toronto is $29,499,000.

Q.How many bedrooms and bathrooms does this property have?

This property features 0 bedrooms and 0 bathrooms.

Q.What property type and architectural style is 464-468 Winona Drive, Toronto, ON ?

464-468 Winona Drive, Toronto, ON is a Vacant Land () featuring a basement.

Q.What key property features does 464-468 Winona Drive, Toronto, ON offer?

Key property features include: Park, Public Transit, School, School Bus Route.

Q.What heating and cooling systems are installed?

Heating is provided via standard central heat and cooling via .

Location

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464-468 Winona Drive, Toronto, ON

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Neighborhood Safety Index

Neighborhood Safety & Crime Analytics

Oakwood Village, Toronto

SAFETY RATING8.9 / 10
Low Incident Area
Total Annual Incidents283 incidents / yr
Average Per Month23.6 incidents / mo
Population Benchmark23,504 residents
Personal Safety
Moderate

137 assaults (583.3/100k)

Property Security
Moderate

47 B&E (200.1/100k)

Auto Theft Risk
Elevated

49 thefts (208.6/100k)

1-Year Trend
â–˛ +6.8%

Elevated vs previous year

How Per-Capita Rate (Per 100,000 Residents) Is Calculated:

Formula: (Annual Occurrences / Population) Ă— 100,000. This standard policing calculation normalizes incident frequencies across different population sizes, allowing accurate safety comparisons between quiet residential pockets and dense urban centres.

Source: Toronto Police Service (TPS) ArcGIS Open Data
Halton & GTHA Police Network

Disclaimer: Crime and safety analytics are compiled from official municipal and regional police open data records for general consumer informational and demographic research purposes only. Data is deemed reliable but is not guaranteed and does not constitute a legal representation or guarantee of future safety.

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Property History

No historical data available for this property.

This could be the first listing for this address.

Pricing & Value Insights

Data-driven valuation for 464-468 Winona Drive, Toronto, ON M6C 3T7

Estimated Sales Range
$1.2M - $1.4M

Based on 0 recent similar sales in the pocket.

Market Speed
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Properties in this area are selling at a steady pace.

Market Trend
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Mortgage & Affordability Audit

Calculate your monthly payment, minimum downpayment, and land transfer taxes for this home in Toronto.

Configure Loan Settings

Interest Rate4.00%
Down Payment$8,849,700 (30.0%)
* Minimum Canadian down payment required for this price is $5,899,800.
Amortization Period30 Years
Estimated Monthly Payment$98,191Based on a loan of $20,649,300 over 30 years.
Purchase Price$29,499,000
Loan Amount$20,649,300
Provincial Land Transfer Tax:$723,950
Toronto Municipal Land Transfer Tax:$723,950
Total Estimated Closing Taxes:$1,447,900

About Purchasing a Home in Toronto, ON

For a property listed at $29,499,000 in Toronto, the legal minimum down payment is $5,899,800 under current Canadian banking regulations. This calculation applies a 5% requirement on the first $500,000, 10% on the next $499,999, and a flat 20% on any amount exceeding $1,000,000.

Additionally, buyers in Ontario must budget for the Provincial Land Transfer Tax, which is estimated at $723,950 for this transaction. Since the property is located in Toronto, a municipal land transfer tax of $723,950 also applies, bringing the total estimated land transfer taxes to $1,447,900.

Similar Listings in Oakwood Village, Toronto

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Oakwood Village, Toronto Neighborhood Guide

Comprehensive city-wide demographics, local real estate stats, and school rankings for Oakwood Village, Toronto.

Verified Local Data
City Population2,794,356
City Median Age39.2 Yrs
City Ownership48% Owners
Avg Area List Price$1,583,510

People & Families

Age Distribution

Household Composition

One-person households
32%
Families with children
36%
Couples without children
24%
Other households
8%

Top Ethnic Origins

Chinese11%
English9%
Canadian8%
East Indian8%

Best Schools in Oakwood Village, Toronto

Elementary Schools

Davisville
Public529 Vaughan Road, York, Toronto, Ontario, M4S 1J6
6.2
D'Arcy McGee
Public20 Bansley Avenue, York, Toronto, Ontario, M6E 2A2
3.4
St John Bosco
Public75 Holmesdale Road, York, Toronto, Ontario, M6E 1Y2
6.1
St Alphonsus
Public60 Atlas Avenue, York, Toronto, Ontario, M6C 3N9
6.6
St Thomas Aquinas
Public636 Glenholme Avenue, York, Toronto, Ontario, M6E 3G9
7.0

Secondary Schools

Oakwood
Public991 St. Clair Avenue West, Toronto, Ontario, M6E 1A3
4.6
Loretto
Public151 Rosemount Avenue, Toronto, Ontario, M6H 2N1
5.7

Oakwood Village, Toronto Demographic Home information

Structural Home Types

Tenure (Ownership vs Rental)

Owner-Occupied48%
Rented52%

Need more details or a custom CMA?

Generate a full market evaluation or explore city guides using the sidebar links.

Notice: Market Insights are generated by analyzing real-time data and should be used for informational purposes only. Consult with a licensed professional for exact valuations.

Disclaimer: AI Insights are generated by an automated system and should be used for informational purposes only. While we strive for accuracy using current market data and deep-learning models, these assessments do not constitute professional real estate, legal, or financial advice. All property values, predictions, and scores are estimates. We strongly recommend verifying all property details and conducting independent due diligence with a licensed professional before making any purchase decisions.

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