299 Winona Drive
Toronto (Oakwood Village), ON M6C 3S8
- 3Bedrooms
- 3Bathrooms
- 2Garage
- 1100–1500Sq Ft
- $5,098Tax
- 17×124 ftLot Size
Estimated Value:$1,255,358See Free Estimate Report
This home has sold. It is no longer available.
Property not available for sale or for rent.
Sale & Price History for 299 Winona Drive, Toronto, Oakwood Village
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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 299 Winona Drive, Toronto, Oakwood Village
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.
Key Facts & Features
Property Costs
- Annual Property Tax Amount
- $5,098
- Land Transfer Tax Fee
- $55,310
Rental Items
- Rental Equipment
- Hot Water Tank.
- Basement Type
- Finished
Interior Features
- Laundry Level
- Lower Level
- Interior Extras
- Auto Garage Door Remote, Carpet Free
- Fireplace/Stove
- No
- Fireplace Features
- Electric
- Elevator
- No
Exterior Features
- Pool
- None
- Property Features
- Fenced Yard, Park, Public Transit, School, Place Of Worship
Building
- Building Type
- Semi-Detached
- Building Style
- 2-Storey
- Approx Age
- 51-99
Construction
- Exterior Finish
- Brick
- Roof
- Asphalt Shingle
- Foundation Details
- Concrete Block
- Special Designation
- Unknown
Lot
- Lot Front
- 17.17 ft
- Lot Depth
- 123.83 ft
- Lot Size
- 17.16 x 123.83 Feet (*S/T & T/W Tb98490; Toronto (York))
- Lot Size Code
- 17.16 x 123.83 Feet (*S/T & T/W Tb98490; Toronto (York))
Inclusions
- Inclusions
- All existing appliances, light fixtures and window coverings.
Parking & Garages
- Garage Type
- Detached
- Garage Spaces
- 2
- Parking Spaces
- 2
- Total Garage And Parking Spaces
- 2
Heating & Cooling
- Heat Source
- Gas
- Heat Type
- Forced Air
- Air Conditioning
- Central Air
- Water
- Municipal
- Sewers
- Sewer
- Bedrooms
- 3
- Washrooms
- 3
- Kitchens
- 1
Room sizes
- Dining Room4.09 x 2.87Main level, Picture Window, Hardwood Floor, Pot Lights
- Kitchen4.01 x 3.30Main level, Marble Counter, B/I Appliances, Pot Lights
- Living Room3.38 x 3.10Main level, W/O To Yard, 2 Pc Bath, Fireplace
- Primary Bedroom3.71 x 3.20Second level, Vaulted Ceiling(s), Picture Window, Double Closet
- Bedroom 23.43 x 3.05Second level, Hardwood Floor, Window, Pot Lights
- Bedroom 33.56 x 2.34Second level, Hardwood Floor, B/I Closet, Pot Lights
- Recreation4.34 x 3.89Lower level, Open Concept, Pot Lights, 4 Pc Bath
- Laundry—Lower level, Open Concept, Pot Lights, Closet
Washrooms
- 2-piece, Main
- 4-piece, Second
- 4-piece, Basement
- Area
- Toronto C03
- Municipality
- Toronto
- Neighbourhood
- Oakwood Village
- Main cross streets
- Oakwood Ave. & St. Clair Ave.
- Zoning
- Residential
- Directions
- Oakwood Ave. & St. Clair Ave.
- MLS® number
- C12457626
- Data source
- Toronto Regional Real Estate Board
- Status change
- 2025-10-27
- Listed on
- 2025-10-10
- Days on market
- 17 days
- Possession type
- Flexible
- Co-op commission
- 2.5% + HSt
- Seller
- Listed by
- RE/MAX NOBLECORP REAL ESTATE
Home Market Value
Current home valuation for 299 Winona Drive, Toronto, Oakwood Village, Toronto, ON. Listed for $1,559,000
HOMEH Estimate
$1,255,358
Estimated Sales Range
$878,751 - $1,631,965
HOMEH Estimate for 299 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
$311,800
| Scenario 1 | Scenario 2 | Scenario 3 | Scenario 4 | |
|---|---|---|---|---|
−Down payment | % $ | % $ | % $ | % $ |
+CMHC insurance | $0 | $0 | $0 | $0 |
=Total mortgage | $1,247,200 | $1,169,250 | $1,091,300 | $1,013,350 |
Amortization | ||||
Mortgage rate | % | % | % | % |
| Payment frequency | ||||
=Mortgage payment | $6,089monthly | $5,709monthly | $5,328monthly | $4,948monthly |
Land Transfer Tax
$27,655
$27,655
$55,310
Around this home
Data provided by OpenStreetMap & Fraser Institute School Rankings
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