7 days on market
Virtual Tour360°
$1,399,000
For Sale

299 Winona Dr

Oakwood Village, Toronto

3+null Bed|3 Bath|Yes|7 days on market

$1,399,000

Buy with Dwelly and Save $13,990

Or call Dwelly at: (647) 797-1133

Home Details

Taxes
$425 / month
Total Parking Spots
2
Driveway
Lane, Private
Garage Spaces
2
Furnished
No
Lot Size
17.17 x 123.83 Feet
Move-in Date
60 Days/Flex
Building Age
51-99 Years
Hydro Included
No
Heating
Forced Air
Water Included
No
Kitchens
1
Family Room
Yes
Basement
Finished
Fireplace
N
Air Conditioning
Central Air
Central Vaccum
No
Laundry Access
Lower
Exterior
Brick
Zoning
Residential
Sewer
Sewers
Property Type
Semi-Detached
Style
2-Storey
Status
New
Give Money

Buy with Dwelly and save $13,990 refund

Refunds vary by sale price, market and are subject to a minimum commission. Please get in touch and read the Refund Terms and Conditions to learn more.

Listing 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.
All existing appliances, light fixtures and window coverings.

Property History

or to view this property's history
Listing DateDOMList PriceSold PriceEventMLS ID
Oct 1, 20205$1,049,900$1,115,000SoldC4936387
Apr 10, 20067$299,000$381,000SoldC876839

Rooms

Room dimensions for 299 Winona Dr, Toronto
Dining
3 x 39 sqft
Kitchen
3 x 39 sqft
Living
3 x 39 sqft
Foyer
3 x 39 sqft
Primary
3 x 39 sqft
2nd Br
3 x 39 sqft
3rd Br
3 x 39 sqft
Rec
3 x 39 sqft
Laundry
3 x 39 sqft

Market Trends and Insights

Mortgage Calculator

Your estimated monthly payment for 299 Winona Dr is 7322

Price

$

Rate

%

Ammortization

Down Payment

$

Total Mortgage


Purchase Price$1399000
Down Payment$279800
Mortgage Insurance$0
Total Mortgage$1119200

Monthly Payment


Mortgage Payment$6897
Property Taxes$425
Maintenance Fees$0
Monthly Payment$7322
$7322
monthly

Sold Comparables

Sold Comparables homes near 299 Winona Dr, Toronto

About 299 Winona Dr, Toronto

Located at 299 Winona Dr , this Toronto house is available for sale. This property was listed for $1,399,000 on Tue Sep 30 2025. This house's size is 1100-1500 Sqft. It has 3 bedrooms and 3 bathrooms. The property includes the following rooms: Dining, Kitchen, Living, Foyer, Primary, 2nd Br, 3rd Br, Rec, Laundry. This property comes with 2 parking spots. 299 Winona Dr, Toronto is situated in the Oakwood Village neighbourhood.


MLS#: C12433756 · $1,399,000 · 3 bedroom house in Oakwood Village, Toronto