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NEXT Open House + more
Oct 04, 2025 02:00 PM - 04:00 PM EDT

299 Winona Drive
Oakwood Village Toronto M6C 3S8

$1,399,000
Residential Freehold beds: 3 baths: 3.0

Main Photo: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 1: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 2: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 3: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 4: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 5: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 6: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 7: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 8: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 9: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 10: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 11: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 12: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 13: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 14: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 15: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 16: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 17: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 18: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 19: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 20: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 21: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 22: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 23: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 24: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 25: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 26: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 27: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 28: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 29: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 30: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 31: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 32: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 33: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Photo 34: 299 Winona Drive in Toronto: Oakwood Village House for sale (Toronto C03)  : MLS®# C12433756
Open House - Oct 04, 2025
02:00 PM - 04:00 PM EDT
NOTES: Open House on Saturday, October 4, 2025 2:00PM - 4:00PM
Open House - Oct 05, 2025
02:00 PM - 04:00 PM EDT
NOTES: Open House on Sunday, October 5, 2025 2:00PM - 4:00PM
Status:
Active
Prop. Type:
Residential Freehold
MLS® Num:
C12433756
Bedrooms:
3
Bathrooms:
3
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.
Property Type:
Residential Freehold
Property Sub Type:
Semi-Detached
Property Attached:
Yes
Home Style:
2-Storey
Approx. Age:
51-99
Total Approx Floor Area:
1100-1500
Depth:
123'10"
Frontage:
17'2"
Lot Details:
17.16 x 123.83 Feet (*S/T & T/W Tb98490; Toronto (York))
Direction Faces:
East
Bedrooms:
3
Bathrooms:
3.0
Water supply:
Municipal
Kitchens:
1
Bedrooms Above Grade:
3
Kitchens Above Grade:
1
# Main Level Bedrooms:
0
# Main Level Bathrooms:
0
Rooms Above Grade:
7
Rooms Below Grade:
1
Rooms:
6
Zoning:
Residential
Heating type:
Forced Air
Heating Fuel:
Gas
Fireplaces:
1
Cooling:
Yes
Foundation:
Concrete Block
Roof:
Asphalt Shingle
Basement:
Finished
Fireplace Features:
Electric
Fireplace/Stove:
No
Attached Garage:
No
Garage:
Detached
Garage Spaces:
2.0
Parking Features:
Lane, Private
Parking Spaces:
0
Total Parking Spaces:
2.0
Family Room:
No
Possession Details:
60 Days/Flex
Pool:
None
HST Applicable To Sale Price:
Included In
Taxes:
$5,097.62 / 2025
Assessment:
$- / -
Toronto
Toronto C03
Oakwood Village
Fenced Yard, Park, Public Transit, School, Place Of Worship
Irregular Lot
Auto Garage Door Remote, Carpet Free
Hot water tank.
All existing appliances, light fixtures and window coverings.
Brick
No
Floor
Type
Size
Other
Main
Dining Room
12'11" × 10'9½"
Picture Window, Hardwood Floor, Pot Lights
Main
Kitchen
14'5¼" × 9'8"
Marble Counter, B/I Appliances, Pot Lights
Main
Living Room
13'5" × 12'11"
W/O To Yard, 2 Pc Bath, Fireplace
Second
Primary Bedroom
12'11" × 10'2"
Vaulted Ceiling(s), Picture Window, Double Closet
Second
Bedroom 2
8'7½" × 7'2¼"
Hardwood Floor, Window, Pot Lights
Second
Bedroom 3
12'3" × 10'10"
Hardwood Floor, B/I Closet, Pot Lights
Lower
Recreation
14'3" × 12'11⅛"
Open Concept, Pot Lights, 4 Pc Bath
Lower
Laundry
11'1" × 6'9"
Open Concept, Pot Lights, Closet
Special Designation:
Unknown
Sewers:
Sewer
Air Conditioning:
Central Air
Central Vacuum:
No
Seller Property Info Statement:
No
Ensuite Laundry:
No
Laundry Level:
Lower Level
Date Listed:
Sep 30, 2025
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Listed by RE/MAX NOBLECORP REAL ESTATE
Data was last updated October 3, 2025 at 08:15 PM (UTC)
Area Statistics
Listings on market:
15
Avg list price:
$1,075,000
Min list price:
$729,000
Max list price:
$2,168,000
Avg days on market:
15
Min days on market:
1
Max days on market:
142
These statistics are generated based on the current listing's property type and located in Oakwood Village. Average values are derived using median calculations. This data is not produced by the MLS® system.
ALEX PRASOULIS
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.