464-468 Winona Drive, Toronto, ON

$29,499,000
MLS#:C12554262
0 beds
0 baths
Residential Freehold
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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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Key Features

000
Property Type
Residential Freehold

Additional Details

StatusSold Conditional
Listed Date11/18/2025
Transaction TypeFor Sale

Property Details

Property Sub-TypeVacant Land
Lot Size71 × 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

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Features

Property Features

Park, Public Transit, School, School Bus Route

Interior Features

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Community Features

Location

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464-468 Winona Drive, Toronto, ON
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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 C03, 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.

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Mortgage & Affordability Audit

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

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Interest Rate5.25%
Down Payment$5,899,800 (20.0%)
* Minimum Canadian down payment required for this price is $5,899,800.
Amortization Period25 Years
Estimated Monthly Payment$140,632Based on a loan of $23,599,200 over 25 years.
Purchase Price$29,499,000
Loan Amount$23,599,200
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.

Nearby Listings

Distance:

No current listings found in Toronto.

City & 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$1,395,665

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%

Local Schools Guide

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 Alphonsus
Public60 Atlas Avenue, York, Toronto, Ontario, M6C 3N9
6.6
St John Bosco
Public75 Holmesdale Road, York, Toronto, Ontario, M6E 1Y2
6.1
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

Homes & Housing

Structural Home Types

Tenure (Ownership vs Rental)

Owner-Occupied48%
Rented52%

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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.