$849,000
344 Winona Drive, Toronto C03, ON M6C 3T3
3 Beds
2 Baths
1 Parking
Situated on a rare corner lot on a quiet cul-de-sac, this home is filled with opportunity, and future potential. With a exceptional outdoor space, garage, and exciting garden suite potential (garden suite report available), this is the kind of property that rarely becomes available in this coveted neighbourhood. Whether you're a 1st time buyer or a renovator looking for your next project, this home offers the perfect canvas to create something special. Enjoy summer entertaining, gardening, play space, and future expansion possibilities. Inside, the sun-filled open-concept main floor offers a bright and airy feel, featuring 3 bedrooms, 2 bathrooms, a high-ceiling basement with a separate entrance, and a functional layout ready for your personal vision. An enclosed sunroom/mudroom adds everyday practicality with space for strollers, bikes, and daily gear, while also offering a cozy retreat to relax and enjoy your morning coffee. Practical upgrades include updated electrical, metal roof, furnace, central air conditioning and a backwater valve. Just a short stroll to St. Clair West cafés, restaurants, and shops, Wychwood Barns farmers market, Cedarvale ravine, and Leo Baeck Day School, with quick access to the TTC, subway, Allen Road, and the 401 - making commuting and weekend exploring a breeze. A wonderful opportunity to put down roots in a welcoming, community-focused neighbourhood where everything is right at your fingertips!

Property Summary

Property Type Residential Freehold
Property Sub Type Semi-Detached
Transaction Type For Sale
Style 2-Storey
Bedrooms Above Grade 3
Bathrooms 2
Kitchens 1
Basement Separate Entrance, Partially Finished
Exposure West
Possession 30days/TBA

Building

Building Type Semi-Detached
Square Footage 1100-1500
Exterior Brick
Foundation Unknown
Roof Metal
Heating Forced Air
Heat Source Gas
Cooling Central Air
Fireplace No

Measurements

Lot Size 16.1 x 100
Lot Size Units Feet
Frontage 16.1
Depth 100
Total Living Area 1100-1500

Land

Address 344 Winona Drive, Toronto C03, ON M6C 3T3
City Toronto C03
Community Oakwood Village
County / Area Toronto
Cross Street St Clair Ave/Winona Dr
Sewer Sewer
Pool None
Parcel Number 104730548

Parking and Garage

Total Parking 1
Garage Spaces 1
Garage Type Detached

Taxes and Listing Info

List Price $849,000
Annual Taxes $4,719
Tax Year 2026
Status Active
Listing Date 2026-05-21T17:36:22Z
Updated 2026-05-22T19:39:11Z
MLS Number C13156722
Local Market Insight

What Buyers Should Know About 344 Winona Drive, Toronto C03, ON M6C 3T3

This editorial summary helps buyers look beyond the headline price and review the neighbourhood, transit, schools, rental demand, long-term value, and due-diligence items that often matter before booking a showing or submitting an offer.

Neighbourhood Analysis

344 Winona Drive, Toronto C03, ON M6C 3T3 is positioned in Oakwood Village, a part of Toronto C03 where buyers should compare the street setting, nearby amenities, daily travel routes, and surrounding housing stock. For a 2-Storey, the strongest fit often depends on whether the location supports everyday routine as well as the numbers on paper.

School And Family Considerations

Families reviewing this Semi-Detached should confirm school boundaries directly with the local school boards before relying on listing notes. It is also worth checking walkability to parks, childcare, recreation centres, libraries, and community facilities because these details can influence both lifestyle value and future resale demand.

Transit And Access

The location should be assessed around commute patterns, access to St Clair Ave/Winona Dr, public transit options, parking availability, and drive times to employment areas. A property with 1 parking and practical road access can appeal to buyers who need convenience without giving up neighbourhood quality.

Investment Potential

At $849,000, buyers should compare recent nearby sales, days on market, condition, lot utility, and the cost of future repairs or upgrades. The property shows 3 bedrooms, 2 bathrooms, basement details marked as Separate Entrance, Partially Finished, and a lot size of 16.1 x 100, all of which can affect value.

Rental Demand

If this property is being reviewed as a rental or investment, demand should be measured by bedroom count, transit access, employment access, nearby schools, parking, and the condition of the unit or home. In Toronto C03, rental appeal usually improves when a property is easy to maintain and simple for tenants to live in.

Local Attractions And Amenities

Buyers should look at grocery access, restaurants, trails, parks, shopping, medical services, and weekend amenities around Oakwood Village. These features do not always appear in the MLS data, but they can make a major difference in how the home feels after move-in and how future buyers compare it.

Builder, Condition, And Due Diligence

For resale homes, review renovations, permits, roof and mechanical age, exterior condition, inclusions, and rental items. For condo or newer properties, review building history, maintenance fees, reserve fund information, rules, amenities, and future cost exposure. A showing and document review should confirm anything not visible in the listing.

Nearby Infrastructure

Infrastructure matters because transit improvements, road projects, schools, parks, commercial growth, and employment nodes can change how an area performs over time. For 344 Winona Drive, Toronto C03, ON M6C 3T3, buyers should check municipal plans, nearby construction, zoning context, and future projects that may affect enjoyment or resale value.

This section is informational only. Buyers should verify schools, measurements, rental rules, taxes, zoning, and property condition with the appropriate professionals before making a decision.

Listing data is provided through PropTx/MLS data services and is deemed reliable but not guaranteed. Listings are subject to change without notice.