299 Winona Drive

299 Winona Drive
299 Winona Drive
299 Winona Drive
+31
3
 bed
3
 bath
2
 parking
1100 - 1500
 sqft
Semi-Detached
$1,399,000
For Sale
23 hours
 on site
$1,399,000
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Size
-
Lot size
2126 sqft
Street frontage
-
Possession
60-89 days
Price per sqft
$933 - $1,272
Taxes
$5,097.62 (2025)
Parking Type
-
Style
2-Storey
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Description
Step inside and prepare for the wow factorthis solid, sturdy home has been fully 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 insulation, electrical, plumbing, windows, doors, furnace, AC, and hot water tank. Every detail has been rebuilt with exceptional quality. Inside, youll 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.
Broker: RE/MAX NOBLECORP REAL ESTATE
MLS®#: C12433756
Property details
Parking:
2
Parking type:
-
Property type:
Semi-Detached
Heating type:
Forced Air
Style:
2-Storey
MLS Size:
1100-1500 sqft
Lot front:
17 Ft
Lot depth:
123 Ft
Listed on:
Sep 30, 2025
Show all details
Rooms
LevelNameSizeFeatures
Main
Living Room
13.4 x 12.9 ft
Second
Primary Bedroom
10.2 x 12.9 ft
Main
Foyer
3.3 x 3.3 ft
Show all
Instant estimate:
orto view instant estimate
$2,087
higher than listed price
i
High
$1,463,980
Mid
$1,401,087
Low
$1,341,661
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About 299 Winona Drive

Located at 299 Winona Drive, this York semi detached house is available for sale. 299 Winona Drive has an asking price of $1399000, and has been on the market since September 2025. This semi detached house has 3 beds, 3 bathrooms and is 1100-1500 sqft. 299 Winona Drive resides in the York Humewood-Cedarvale neighbourhood, and nearby areas include Hillcrest | Bracondale Hill, Corso Italia, Fairbank and Forest Hill.

There are a lot of great restaurants around 299 Winona Dr, Toronto. If you can't start your day without caffeine fear not, your nearby choices include Krave Coffee. For grabbing your groceries, Atlas Grocery is only steps away.

If you are looking for transit, don't fear, there is a Bus Stop (Oakwood Ave at Earlsdale Ave) a 3-minute walk. For drivers, the closest highway is Allen Rd and is within a few minutes drive from 299 Winona Dr, making it easier to get into and out of the city getting on and off at Lawrence Ave W.