Semi-Detached House for sale at 299 Winona Drive, Toronto, Ontario, M6C 3S8 - Oakwood Village - MLS: C12433756

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299 Winona Drive

Toronto, Ontario, M6C 3S8 - Oakwood Village

$1,399,000

Virtual Tour

Neighbourhood

Oakwood Village
Major Intersection

Oakwood Ave. & St. Clair Ave.

Listed Since: 6 day(s)
Last update: 4 day(s) ago

Virtual Tour

Overview

Property Type

Semi-Detached, 2-Storey
Bedrooms

3
Bathrooms

3
Basement

Finished
Kitchen

1
Total Parking

2 Detached Garage
Lot Size

17.17x123.83 (Feet)
Taxes

$5,097.62 (2025)
Type

Freehold

Property Description

Property description for 299 Winona Drive, Toronto

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.

Listed by RE/MAX NOBLECORP REAL ESTATE

Property details

MLS #

C12433756
Sq. Ft

1100-1500
Sq. Ft. Source

MLS
Lot Irregularities

n/a
Year Built

51-99
Pool

None
Drive

Lane, Private
Garage

Detached, 2 spaces
Total Parking

2
Family Room

N
Den

N
Exterior

Brick
Fireplace

N
Roof

Asphalt Shingle
Foundation

Concrete Block
Elevator

n/a
Water View

n/a
Laundry Level

Lower
Heat

Forced Air
A/C

Central Air
Water

Municipal
Water Supply

n/a
Sewers

Sewers
Central Vac

N

MLS #

C12433756
Sq. Ft

1100-1500
Sq. Ft. Source

MLS
Lot Irregularities

n/a
Year Built

51-99
Pool

None
Drive

Lane, Private
Garage

Detached, 2 spaces
Total Parking

2
Family Room

N
Den

N
Exterior

Brick
Fireplace

N
Roof

Asphalt Shingle
Foundation

Concrete Block
Elevator

n/a
Water View

n/a
Laundry Level

Lower
Heat

Forced Air
A/C

Central Air
Water

Municipal
Water Supply

n/a
Sewers

Sewers
Central Vac

N

Dining

3.29 x 3.93 ft Main level

Picture Window, hardwood floor, Pot Lights
Kitchen

4.4 x 2.95 ft Main level

Marble Counter, B/I Appliances, Pot Lights
Living

4.09 x 3.93 ft Main level

W/O To Yard, 2 Pc Bath, Fireplace
Primary

3.1 x 3.93 ft 2nd level

Vaulted Ceiling, Picture Window, Double Closet
Foyer

1.0 x 1.0 ft Main level

Closet, hardwood floor, Open Stairs
2nd Br

2.63 x 2.19 ft 2nd level

hardwood floor, Window, Pot Lights
3rd Br

3.73 x 3.3 ft 2nd level

hardwood floor, B/I Closet, Pot Lights
Rec

4.34 x 3.94 ft Lower level

Open Concept, Pot Lights, 4 Pc Bath
Laundry

2.06 x 3.37 ft Lower level

Open Concept, Pot Lights, Closet

Contact Manoj Kukreja

Sales Representative,
Century 21 People’s Choice Realty Inc.,
Brokerage
(647) 576 - 2100

Open house for 299 Winona Drive, Toronto

Property History

Property history for 299 Winona Drive, Toronto

This property has been sold 2 times before. Create your free account to explore sold prices, detailed property history, and more insider data.

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Neighbourhood Amenities & Points of Interest

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Local Real Estate Price Trends for Semi-Detached in Oakwood Village

Active listings

Average Selling Price of a Semi-Detached

September 2025

$1,002,500

Last 3 Months

$939,833

Last 12 Months

$1,106,805

September 2024

$1,117,667

Last 3 Months LY

$1,101,722

Last 12 Months LY

$906,561

Change

-10%

Change

-15%

Change

22%

Number of Semi-Detached Sold

September 2025

Last 3 Months

Last 12 Months

September 2024

Last 3 Months LY

Last 12 Months LY

Change

33%

Change

67%

Change

67%

How many days Semi-Detached takes to sell (DOM)

September 2025

Last 3 Months

Last 12 Months

September 2024

Last 3 Months LY

Last 12 Months LY

Change

76%

Change

110%

Change

100%

Average Selling price

Inventory Graph

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First time home buyer

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Down Payment(%)*

Additional information

Provincial Land Transfer Tax

Ontario Land Transfer Tax Rebate

Toronto Land Transfer Tax

Toronto Land Transfer Tax Rebate

PST on CMHC Insurance Premium

Lawyer Fees

$2,825

Government Registration Fee's

$164

Title Insurance

Closing Cost Total

Total Cash flow for purchasing this property

Provincial Land Transfer Tax

Ontario Land Transfer Tax Rebate

Toronto Land Transfer Tax

Toronto Land Transfer Tax Rebate

PST on CMHC Insurance Premium

Lawyer Fees

$2,825

Government Registarion Fee's

$164

Title Insurance

Purchase Price

Down Payment($)

Down Payment(%)*

First time home buyer

* A down payment of less than 20% is permitted only for first-time home buyers purchasing their principal residence. The minimum down payment required is 5% for the portion of the purchase price up to $500,000, and 10% for the portion between $500,000 and $1,500,000. For properties priced over $1,500,000, a minimum down payment of 20% is required.