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Detached for sale at 362 Winston Road, Oakville - 3 bedroom, 4 bathroom - Photo 1 of 26
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$1,974,000

362 Winston Rd

Oakville, ON L6L 4W5

362 Winston Rd, Oakville — Listed at $1,974,000. 3 bedroom, 4 bathroom 1 1/2 Storey Detached. MLS® W13830254.

3Beds
4Baths
2000-2500sqft
Detached
1 1/2 Storey
8Parking
$9,003.51Taxes/yr · 2026
See similar homes in this price range

Description

Welcome to 362 Winston Road, an exceptional South Oakville residence situated on one of the area's most prestigious and highly sought-after streets, surrounded by stunning custom-built multi-million-dollar homes. Just a short walk to the renowned Appleby College, this beautifully renovated bungalow offers an outstanding blend of elegance, comfort, and convenience. Thoughtfully updated and impeccably maintained, the home features a substantial rear addition showcasing a spacious family room with a cozy gas fireplace and a walkout to the private west-facing backyard. Large windows adorned with solid wood California shutters fill the home with natural light, while hardwood flooring throughout the main level adds warmth and timeless appeal. The updated kitchen overlooks the mature backyard and features a skylight that floods the space with sun. Adjacent to the kitchen, a charming breakfast nook with a bay window provides the perfect spot for casual dining, while a separate formal dining room offers an elegant setting for entertaining. Privately located on the upper level, the impressive primary retreat features a spacious sitting area, skylight, generous closet space, and a 5-piece ensuite. Two additional bedrooms and a 4-piece bathroom complete the main floor. The finished lower level expands the living space with a large recreation room, office, gym or potential additional bedroom, laundry area, abundant storage, and another full bathroom. With four full bathrooms throughout the home, there is plenty of room for family and guests. Outside, a rare oversized attached four-car garage and a private west-facing backyard offer exceptional outdoor enjoyment, mature landscaping, and beautiful sunset views. Ideally located close to high-ranking public and private schools, parks, transit, shopping, and major highways, this solidly built home presents a rare opportunity to own in one of South Oakville's most desirable enclaves.

Property Details

Property TypeDetached
Style1 1/2 Storey
Community1020 - WO West
Approximate Age51-99
Rooms11
Kitchens1
Washrooms4
Square Feet2000-2500 sqft
Lot Dimensions75.13 × 155.94 ft
Fronting OnWest
Dir/Cross StRebecca/Fourth Line
Garage TypeAttached
Garage Parking Spaces4
DrivePrivate, Private Double
Parking Drive Spaces4
Total Parking Spaces8
ExteriorStucco (Plaster)
RoofAsphalt Shingle
FoundationConcrete Block
BasementCrawl Space, Full, Unfinished, Finished
Fireplace FeaturesNatural Gas
Heating TypeForced Air
Heating SourceGas
A/CCentral Air
SewersSewer
Taxes (2026)$9,003.51
HSTIncluded In
Listed Date9/25/2026
Days on Market48 days
PossessionFlexible

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Listing Courtesy of: Royal LePage Realty Plus Oakville, Brokerage

MLS® #W13830254

TRREBMLS®

The listing data is provided under copyright by the Toronto Regional Real Estate Board (TRREB). The listing data is deemed reliable but is not guaranteed accurate by TRREB. The trademarks REALTOR®, REALTORS®, and the REALTOR® logo are controlled by The Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by CREA and identify the quality of services provided by real estate professionals who are members of CREA. Used under license.

© 2026 Toronto Regional Real Estate Board. All rights reserved.

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HouseIndex Take: 362 Winston Road

This detached (1 1/2 Storey) is located in the 1020 - WO West neighbourhood of Oakville.

The home offers 3 bedrooms, 4 bathrooms.

Features include a crawl space, full, unfinished, finished basement, 8 parking spaces including a 4-car garage, a fireplace.

Additional details: lot dimensions of 75.13 × 155.94 feet.

About Oakville Real Estate

This Detached is located in the 1020 - WO West community in Oakville. Oakville is an affluent lakefront town in Halton Region known for heritage estates in Old Oakville, a thriving downtown core along Lakeshore Road, and excellent schools. The QEW provides quick access to Toronto and Hamilton, while the Oakville GO station offers 30-minute service to Union. It consistently ranks among Canada's best places to live. Detached homes in Oakville are in high demand among families seeking space, privacy, and long-term equity growth.

Lakefront trails & Bronte HarbourTop-ranked Halton District School Board30-minute GO Train to Union StationBoutique shops along Lakeshore Road
~35 min commute to downtown TorontoWalkability: Walkable downtown — suburban outer areas
View full Oakville neighbourhood guide →