
244 Winona Drive
Toronto (Oakwood Village), ON M6C 3S2
- 4Bedrooms
- 4Bathrooms
- 0Garage
- 2000–2500Sq Ft
- $5,772Tax
- 28×102 ftLot Size
- Estimated Value:$1,654,828See Free Estimate Report

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Free Home EvaluationHow Much Is My Home Worth?Homes for Sale NearbySale & Price History for 244 Winona Drive, Toronto, Oakwood Village
| Start Date | End Date | Price | Event | MLS# |
|---|---|---|---|---|
| 2025-05-14 | 2025-09-14 | Login to See Prices | Expired | c12149556 |
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*Sold prices and complete sale & price history are regulated data. Under the Trust in Real Estate Services Act, 2002 (TRESA) and the rules of the Real Estate Council of Ontario (RECO), and pursuant to the Multiple Listing Service® rules of the Canadian Real Estate Association (CREA) and the Toronto Regional Real Estate Board (TRREB), this information may be shown only to registered users who have agreed to the applicable terms of use (a Virtual Office Website, or "VOW," arrangement). HOMEH Inc., Brokerage therefore provides it to signed-in members only. Creating an account is free and takes under a minute.
About 244 Winona Drive, Toronto, Oakwood Village
Looking for a property that pays you to live in it? Congratulations, youve hit the real estate jackpot. This gem in the heart of Toronto has three separate units, meaning you can live in one and let the others foot the bills. Thats right collect rent while lounging in your pajamas. The top floor is already pulling its weight with $5,000/month in rent, so youre off to a strong start. Plus, theres a generous rear addition that gives you plenty of room to stretch out, host friends, or finally start that indoor herb garden youve been talking about. With recent updates, the home is fully move-in ready. Theres even a legal front parking pad, because circling the block in Toronto traffic is so 2020. Just steps to St. Clair Wests shops and restaurants, this location is hotter than your neighbors Wi-Fi signal. So whether youre an investor, a savvy house-hacker, or just someone who loves the idea of tenants paying your mortgage 244 Winona Drive is ready to make you laugh all the way to the bank.
Key Facts & Features
Property Costs
- Annual Property Tax Amount
- $5,772
- Land Transfer Tax Fee
- $61,430
- Basement Type
- Finished
Interior Features
- Laundry Level
- Lower Level
- Interior Extras
- Water Heater
- Security Features
- Carbon Monoxide Detectors, Security System, Smoke Detector
- Fireplace/Stove
- Yes
- Elevator
- No
Exterior Features
- Pool
- None
- Property Features
- Park, Public Transit, School
Building
- Building Type
- Detached
- Building Style
- 1 1/2 Storey
Construction
- Exterior Finish
- Brick
- Roof
- Asphalt Shingle
- Foundation Details
- Concrete
- Special Designation
- Unknown
Lot
- Lot Front
- 27.50 ft
- Lot Depth
- 102.33 ft
Inclusions
- Inclusions
- Electric light fixtures, window coverings. Appliances; main floor - electric stove, hood vent, fridge, dishwasher, microwave.Upper level - fridge, countertop stove top, built in oven, dishwasher. Basement - fridge, electric oven, clothes washer and dryer
Parking & Garages
- Garage Type
- None
- Garage Spaces
- 0
- Parking Spaces
- 0
- Total Garage And Parking Spaces
- 0
Heating & Cooling
- Heat Source
- Gas
- Heat Type
- Forced Air
- Air Conditioning
- Other
- Water
- Municipal
- Sewers
- Sewer
- Bedrooms
- 4
- Washrooms
- 4
- Kitchens
- 3
- Family / bonus room
- Yes
Room sizes
- Living Room—Main level, Fireplace, Overlooks Frontyard, French Doors
- Dining Room—Main level, French Doors, Crown Moulding, Hardwood Floor
- Kitchen—Main level, Tile Floor
- Office—Main level, Large Closet, Hardwood Floor
- Bedroom 2—Main level, 3 Pc Ensuite, Large Closet, Overlooks Backyard
- Living Room—Second level, Overlooks Frontyard, Open Concept, Vaulted Ceiling(s)
- Dining Room—Second level, Combined w/Living, Hardwood Floor
- Kitchen—Second level, Open Concept
- Office—Second level, Large Window, Closet, Hardwood Floor
- Primary Bedroom—Second level, Large Closet, Overlooks Backyard, Hardwood Floor
- Living Room—Basement level, Open Concept, Broadloom, Above Grade Window
- Bedroom 3—Basement level, Broadloom
- Dining Room—Basement level, Open Concept, Combined w/Living
- Laundry—Basement level, Laundry Sink, Ceramic Floor
Washrooms
- 4-piece, Main
- 3-piece, Main
- 4-piece, Second
- 3-piece, Basement
- Municipality
- Toronto
- Neighbourhood
- Oakwood Village
- Main cross streets
- Oakwood Ave and St. Clair Ave. W
- Directions
- Oakwood Ave and St. Clair Ave. W
- MLS® number
- C12149556
- Data source
- Toronto Regional Real Estate Board
- Status change
- 2025-09-14
- Listed on
- 2025-05-14
- Days on market
- 123 days
- Possession type
- 90+ days
- Co-op commission
- 2.5% +HST
- Seller
- Listed by
- KELLER WILLIAMS REFERRED URBAN REALTY
Home Market Value
Current home valuation for 244 Winona Drive, Toronto, Oakwood Village, Toronto, ON. Listed for $1,712,000
HOMEH Estimate
$1,654,828
Estimated Sales Range
$992,897 - $2,316,759
HOMEH Estimate for 244 Winona Drive, Toronto, Oakwood Village
Calculated with a real agent's CMA method — 45+ years of experience, codified. Not an AI guess.
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Mortgage Payment Calculator
Compare up to 4 down payment scenarios
20% required for homes $1.5M or more
$342,400
| Scenario 1 | Scenario 2 | Scenario 3 | Scenario 4 | |
|---|---|---|---|---|
−Down payment | % $ | % $ | % $ | % $ |
+CMHC insurance | $0 | $0 | $0 | $0 |
=Total mortgage | $1,369,600 | $1,284,000 | $1,198,400 | $1,112,800 |
Amortization | ||||
Mortgage rate | % | % | % | % |
| Payment frequency | ||||
=Mortgage payment | $6,687monthly | $6,269monthly | $5,851monthly | $5,433monthly |
Land Transfer Tax
$30,715
$30,715
$61,430
Around this home
Data provided by OpenStreetMap & Fraser Institute School Rankings
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