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Copyright © 2026 The Canadian Home Realty Inc.
  • Ontario
  • Toronto
  • Oakwood Village
  • 299 Winona Drive
299-winona-drive-toronto-ontario-c12457626
299-winona-drive-toronto-ontario-c12457626
299-winona-drive-toronto-ontario-c12457626
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  • Sold Sold in Oct 2025
  • Semi Detached

299 Winona Drive

Toronto, Oakwood Village
  • 3 Bedrooms
  • 3 Bathrooms
  • 2 Garage
  • Share
Sold Price: $ 1,510,000
3.14%
Listed Price: $ 1,559,000
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Room Details of 299 Winona Drive, Toronto

FloorBedroomsBathrooms
Basement * 1
Ground * 1
Second 3 1

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Key Facts About 299 Winona Drive, Toronto

  • Tax $5,098 / 2025
  • Property Type Residential
  • Building Type Semi-Detached
  • Building Style 2-Storey
  • Building Age 51-99
  • Size 1100 - 1500 feet²
  • Lot Size 17.17 x 123.83 feet
  • Basement Finished
  • Listing # C12457626
  • Data Source PROPTX
  • Days on Market 13
  • Listed On 10/10/2025
  • Updated On 27/10/2025
  • Market Demand
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Description

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, a

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Property Details of 299 Winona Drive, Toronto

Property

  • Property Type Semi Detached
  • Style 2-Storey
  • Fronting On E
  • Community Oakwood Village
  • Municipality Toronto

Inside

  • Bedrooms 3
  • Bathrooms 3
  • Bathroom Details 1, 2pc Main
  • Bathroom Details 1, 4pc Second
  • Bathroom Details 1, 4pc Basement
  • Basement Finished
  • Kitchen 1
  • Rooms 7
  • Family Rooms N
  • Central Vac N
  • Fireplace N

Utilities

  • Water Municipal
  • Cooling Central Air
  • Heating Type Forced Air
  • Heating Fuel Gas

Building

  • Size 1100 - 1500 feet²
  • Architecture Style 2-Storey
  • Exterior Feature Brick
  • Building Age 51-99

Parking

  • Drive Way Lane, Private
  • Garage Type Detached
  • Garage 2
  • Total Parking Places 2

Land

  • Sewer Sewer
  • Frontage 17.17
  • Depth 123.83
  • Zoning Residential
  • Lot Size 17.17 x 123.83 feet
  • Lot Size Code Feet
  • Cross Street Oakwood Ave. & St. Clair Ave.

Features

  • Fenced Yard Y
  • Park Y
  • Public Transit Y
  • School Y
  • Place Of Worship Y

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Our Estimate

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Estimated Rent

$ 4,577

Rental Yield

-26.31%

School Score

7.6/10

Rental Score

1/5

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Rooms

Dining Room (4.09 metre)
Living Room
Level: Main
Kitchen (4.01 metre)
Kitchen
Level: Main
Living Room (3.38 metre)
Dining Room
Level: Main
Primary Bedroom (3.71 metre)
Primary Bedroom
Level: Second
Bedroom 2 (3.43 metre)
Bedroom 2
Level: Second
Bedroom 3 (3.56 metre)
Bedroom 3
Level: Second
Recreation (4.34 metre)
Recreation
Level: Lower
Laundry (2.06X3.37 metre)
Level: Lower

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Expense Breakdown

Monthly Mortgage Payment

$0/monthly

30 Year , 3.99% interest

Cash Expenditure for Home Purchase

$1,000

  • Downpayment
    $0
  • PST on Mortgage Insurance
    $0
  • Land Transfer Tax
    $0
  • Lawyer Fees
    $1,000
  • Title Insurance
    $0

Monthly Expenses After Home Purchase

$569

  • Mortgage Payment
    $0
  • Property Insurance
    $50
  • Property Tax
    $250
  • Phone
    $40
  • Monthly debt payments
    $0
  • Cable
    $60
  • Utilities
    $124
  • Internet
    $45
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MLS® Trusted listing from Toronto Real Estate Board The trademarks MLS®, Multiple Listing Service® and the associated logos identify professional services rendered by REALTOR® members of CREA to effect the purchase, sale and lease of real estate as part of a cooperative selling system.

Copyright:© The Canadian Home Realty Inc. All rights reserved. The Canadian Home Realty Inc is a registered real estate brokerage.

About 299 Winona Drive, Toronto

Welcome to this stunning house for sale in Toronto , located at 299 Winona Drive, Toronto. This semi-detached gem in the vibrant Oakwood Village community has been meticulously transformed from top to bottom, offering a perfect blend of modern living and classic charm. As you step inside, prepare to be wowed by the attention to detail and quality finishes that define this remarkable home.

The property boasts a generous lot size of 17 x 124 feet, providing ample outdoor space for relaxation and entertaining. Although there is no pool, the backyard is designed for gatherings, featuring new decking that invites you to host barbecues or simply enjoy the fresh air. The exterior of the house is elegantly clad in brick, giving it a sturdy and timeless appearance that complements the neighbourhood's character.

Inside this house for sale in Toronto, you will find three bright and spacious bedrooms, each designed to maximise natural light and comfort. The layout includes three bathrooms, with a newly added main-floor bath that adds convenience for family and guests alike. The absence of a den means that the living space is open and airy, allowing for a seamless flow throughout the home.

The heart of the house is undoubtedly the main kitchen, which is beautifully appointed with high-end finishes. Marble countertops and custom built-ins enhance the aesthetic, making it a delightful space for cooking and entertaining. Although there is no additional kitchen, the main kitchen is more than sufficient for all your culinary needs. The finished basement offers extra room for storage or a play area, while the absence of a family room means that the main living areas are designed for versatility and comfort.

One of the standout features of this house for sale in Toronto is the central air conditioning, ensuring that you stay cool during the warmer months. The forced air heating system provides efficient warmth in the winter, making this home comfortable year-round. While there is no fireplace, the modern design and smart-home technology create a warm and inviting atmosphere that feels like a true retreat.

At 299 Winona Drive, Toronto, you’ll also appreciate the convenience of modern amenities such as internet connectivity, which is essential for today’s lifestyle. The property is unfurnished, allowing you to put your personal stamp on the space and make it truly your own. The detached garage provides two spaces for parking, and the private lane driveway ensures easy access to your vehicle.

Situated just steps away from the bustling shops, restaurants, and farmers market on St. Clair Avenue, this house for sale in Toronto offers not only a beautiful home but also a vibrant lifestyle. Cedarvale Park and the nearby ravine trails provide excellent opportunities for outdoor activities, making it an ideal location for families and nature enthusiasts alike.

With a building age of 51-99 years, this semi-detached house has a character and history that new builds often lack. The combination of modern renovations and classic features creates a unique living experience that is hard to find.

In summary, if you’re searching for a house for sale in Toronto that combines modern luxury with a prime location, look no further than 299 Winona Drive, Toronto. This property offers everything you need for a comfortable and stylish lifestyle, making it a must-see for anyone looking to make Oakwood Village their home. Don’t miss your chance to own this exceptional property!

Oakwood Village, nestled in the vibrant city of Toronto, is a charming neighbourhood that beautifully blends urban convenience with a welcoming atmosphere. Characterised by its tree-lined streets and a diverse array of shops, cafes, and restaurants, it offers residents a lively yet relaxed environment. The area is well-connected by public transport, making it easy to explore the wider city, while local parks provide green spaces for leisure and recreation. With a rich cultural tapestry and a strong sense of community spirit, Oakwood Village is an inviting place for those seeking a balance of city life and neighbourhood warmth.

Schools in the Neighbourhood

This property is conveniently located near several educational institutions, making it an excellent choice for families. The closest school is St. Alphonsus Catholic School, just 0.2 km away, offering both English and French instruction for grades JK to 8, with a school rating of 4.9. Humewood Community School, also nearby at 0.5 km, provides a public education in both English and French for grades JK to 8, boasting a rating of 6.8. For secondary education, Forest Hill Collegiate Institute is located 2.3 km from the property, while Loretto College School is 1.2 km away, both offering English instruction for grades 9 to 12, with Loretto rated at 6. Additionally, Marshall McLuhan Catholic Secondary School, 3.2 km away, offers a French curriculum for grades 9 to 12, with a rating of 6.6. Overall, the area features a mix of public and Catholic schools, providing diverse educational options for children of all ages, ensuring families have access to quality education within a short distance from home.

Key Statistics of the Neighbourhood

The area surrounding the property has a population of 484 residents, with an average household size of 2.7. The community is characterized by a relatively mature demographic, with an average age of 40.8 years. Economic indicators show a strong average household income of $144,000, with only 5.6% of the population classified as low-income. The average property price in the area is $1,320,000, reflecting the affluent nature of the community. Socially, 39.24% of the population is single, while a significant 57.14% of households include children, indicating a family-friendly environment. The area is also home to a diverse population, with 22.12% being immigrants. Renters make up 28.57% of the housing situation, and there are no condominiums available in the vicinity. Educational attainment is high, with 68.29% of residents holding a college or university degree. However, 24.39% of the population is not in the labor force, which may reflect various factors such as retirement or other commitments. Overall, this community presents a blend of affluence, family orientation, and educational achievement, making it an attractive area for potential homeowners.

FAQs About 299 Winona Drive, Toronto

How many bathrooms does this property have?

This property features 3 bathroom(s) and 3 bedroom(s).

Does this 3 bedroom property have additional bedrooms or a den?

This Semi Detached property does not have an additional bedroom or a den.

What is the square footage (sqft) of this Semi Detached property?

The total square footage of this Semi Detached 3 bed property in Toronto is 1100 - 1500.

How many parking spaces are available with this property?

There are no parking spaces available with this property.

How many cars can be parked in the garage of 299 Winona Drive?

This property features a garage with space for 2 cars.

What type of garage does this property have?

This property includes an Detached garage with space for 2 cars.

Does this property have a basement?

Yes, this property has a basement.

What type of basement is it?

This property features Finished basement.

Does this property have a swimming pool?

It is not specified whether this property has a swimming pool.

Does this property have a fireplace?

There is no fireplace in this property.

How many kitchens does this property have?

This property includes 1 kitchen(s).

Is there a maintenance fee associated with this property?

Information about the maintenance fee is not available.

Is this property furnished?

Information about whether this property is furnished is not available.

What type of heating system is in place?

The heating system in place is a Forced Air.

What utilities are available for this property?

Information about utilities is not available.

School Rating for 299 Winona Drive, Toronto

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Listing History

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