Front of 299 Winona Drive

299 Winona Drive

Toronto (Oakwood Village)
Terminated
1/34
Ontario Real Estate › Toronto › Oakwood Village
Front of 299 Winona Drive

299 Winona Drive

Toronto (Oakwood Village)
Terminated
See all 34 photos
Semi-DetachedMLS C12433756
Last asked:Terminated Oct 10, 2025
$1,399,000
3 Bedrooms
3 Bathrooms
2 Garage
1.1K~1.5K Sq.Ft.
17.17 x 123.83 ft Lot
$5,098 Tax/yr

Property history

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About this home

299 Winona Drive, Toronto

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.

Auto Garage Door RemoteCarpet FreeFenced YardParkPublic TransitSchool

Facts & features

TypeSemi-Detached
Style2-storey
Built51-99
Size1.1K~1.5K Sq.Ft.
Lot17.17 x 123.83 ft
Tax$5,098 (2025)
HeatingForced air, gas
CoolingCentral air
BasementFinished
Parking2 drive
WaterMunicipal

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Rooms

9 rooms · 3 bathrooms
Main floor4 rooms
  • Foyer3′3″ × 3′3″11 sq.ft.
  • Dining room10′10″ × 12′11″139 sq.ft.
  • Living room13′5″ × 12′11″173 sq.ft.
  • Kitchen14′5″ × 9′8″140 sq.ft.
Second floor3 rooms
  • Primary bedroom10′2″ × 12′11″131 sq.ft.
  • Bedroom 28′8″ × 7′2″62 sq.ft.
  • Bedroom 312′3″ × 10′10″132 sq.ft.
Lower level2 rooms
  • Recreation14′3″ × 12′11″184 sq.ft.
  • Laundry6′9″ × 11′1″75 sq.ft.
Bathrooms3
4-pcSecond4-pcBasement2-pcMain
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Around this home

Oakwood Ave. & St. Clair Ave.
10Walking

Schools nearby

School rating, out of 10.

St Alphonsuselementary · Private · 0.3 km
4.9/10
Rawlinsonelementary · Public · 0.5 km
5.1/10
Humewoodelementary · Public · 0.5 km
6.8/10

Listing details

MLS® numberC12433756
Listed onSep 30, 2025
Days on market10
UpdatedOct 10, 2025
Listing brokerageRE/MAX NOBLECORP REAL ESTATE
Possession60-89 days

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