Was listed for:Expired Sep 14, 2025
$1,712,000

244 Winona Drive

Toronto (Oakwood Village), ON M6C 3S2

Detached House ExpiredNot available

Property not available for sale or for rent.

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Sale & Price History for 244 Winona Drive, Toronto, Oakwood Village

2025-05-14
2025-09-14
Expired
Price
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MLS#
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.

$1,654,828Low confidence
Based on 3 comparable properties
+ $57,172 (3%) above our estimate
See the full analysisFree Every recent nearby sale behind this number

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Mortgage Payment Calculator

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Toronto, ON
Minimum Down Payment Required:20.0%

20% required for homes $1.5M or more

Minimum down payment

$342,400

Scenario 1 Scenario 2 Scenario 3 Scenario 4
−Down payment
%
$
%
$
%
$
%
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+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
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Land Transfer Tax

Provincial

$30,715

Municipal (Toronto)

$30,715

Total Land Transfer Tax

$61,430

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