299 Winona Drive, Toronto C03, ON

$1,559,000
MLS#:C12457626
3 beds
3 baths
1100-1500 sqft
2.0 parking
Residential Freehold
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Description

Property Highlights

Welcome to this remarkable ["2-Storey"] semi-detached located in the coveted neighborhood of Oakwood Village. Expertly crafted featuring premium brick construction, this residence presents an exceptional opportunity offered at $1,559,000 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.

  • 3 Bedrooms and 3 Bathrooms
  • Generous living space spanning 1100-1500 sqft on a premium 17.17 x 123.83 ft lot
  • Features a ["finished"] basement, adding superb versatility for recreation, a home gym, or extra storage
  • 2.0 total parking spaces available with a convenient detached configuration
  • Notable attributes: Auto Garage Door Remote, Carpet Free
  • equipped with ["central air"] central cooling and highly efficient forced air heating via gas

Step inside and prepare for the wow factor, this solid, sturdy home has been reimagined from top to bottom. Sitting on an expansive lot in one of the best locations on Winona, it was taken right down to the studs with new electrical, windows, doors, furnace, AC, and hot water tank. Every detail has been addressed with exceptional quality. Inside, you'll find 3 bright bedrooms and 3 bathrooms, including a newly added main-floor bath. High-end finishes shine throughout: a floating staircase, marble countertops, custom built-ins, surround sound, and a cozy fireplace. The vaulted ceiling in the primary suite creates a true retreat, enhanced with smart-home technology. Outdoors, enjoy an entertainers backyard with new decking perfect for gatherings. Complete with a detached garage and ideally positioned just steps to St. Clairs shops, restaurants, and farmers market, with Cedarvale Park and ravine trails nearby.

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Key Features

Bedrooms
3
Bathrooms
3
Kitchens
1
Living Area
1100-1500 sqft
Property Type
Residential Freehold

Additional Details

StatusSold
Sold DateOctober 27, 2025
Sold price information is available to members only
Listed Date10/10/2025
Transaction TypeFor Sale

Property Details

Property Sub-TypeSemi-Detached
ConstructionBrick
Lot Size17.17 × 123.83 Feet
CountyToronto
Annual Tax$5,097.62
Legal DescriptionPT LT 9 PL 2258 TWP OF YORK AS IN TB98490, S/T & T/W TB98490; TORONTO (YORK) , CITY OF TORONTO

Parking & Garage

Parking Spaces2.0
Garage TypeDetached

Heating & Cooling

Heat SourceGas
Heat TypeForced Air
Cooling["Central Air"]

Features

Property Features

Fenced Yard, Park, Public Transit, School, Place Of Worship

Community Features

Location

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299 Winona Drive, Toronto C03, 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 299 Winona Drive, Toronto C03, ON M6C 3S8

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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Financial Audit

Estimated Costs

Loan Amount$1,247,200
Monthly Mortgage$7,247
Property Tax (Est.)$425
Utilities & Maint.$350
Total Monthly Cost$8,022

Nearby School Rankings

No schools found within 3 km of this property.

Within 2km radiusFraser Institute Ratings

Nearby Listings

Distance:

No current listings found in Toronto C03.

City & Neighborhood Guide

Comprehensive city-wide demographics, local real estate stats, and school rankings for Oakwood Village, Toronto C03.

Verified Local Data
City Population2,794,356
City Median Age39.2 Yrs
City Ownership48% Owners
Avg Area List Price$1,206,698

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
Rawlinson
Public231 Glenholme Avenue, York, Toronto, Ontario, M6E 3C7
4.9
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
J R Wilcox
Public231 Ava Road, York, Toronto, Ontario, M6C 1X3
8.1

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.