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Detached for sale at 366 Winston Road, Oakville - 4 bedroom, 2 bathroom - Photo 1 of 34
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$4,500

366 Winston Rd

Oakville, ON L6L 4W5

366 Winston Rd, Oakville — Listed at $4,500. 4 bedroom, 2 bathroom Bungalow Detached. MLS® W12888432.

4Beds
2Baths
1100-1500sqft
Detached
Bungalow
10Parking
See similar homes in this price range

Description

Experience refined luxury living in the heart of Oakville. This exceptional, fully renovated bungalow blends timeless elegance with modern sophistication, enhanced by custom architectural additions at both the front and rear of the home. Located in one of Oakville's most desirable neighbourhoods-just minutes from Appleby College, the lakefront, top-tier schools, boutique shopping, and vibrant local amenities-this residence offers an unmatched lifestyle of comfort and convenience. Step inside to soaring cathedral and cove ceilings that create an airy, grand atmosphere. The gourmet chef's kitchen is a true centrepiece, featuring custom maple cabinetry, granite countertops, built-in cooktop and wall oven, travertine flooring, and a stunning skylight that fills the space with natural light. The open-concept flow continues with gleaming hardwood floors, multiple skylights, designer pot lighting, and built-in speakers wired throughout for an elevated living experience.The home's thoughtful design extends to the lower level, offering a separate entrance for added flexibility-ideal for extended family, guests, or private workspace needs. A rare oversized garage accommodates up to four vehicles, providing exceptional storage and utility seldom found in rental properties.This is a truly distinguished home that delivers luxury, location, and lifestyle in perfect harmony-an extraordinary opportunity in prestigious Oakville.

Property Details

Property TypeDetached
StyleBungalow
Community1020 - WO West
Rooms5+3
Kitchens1
Washrooms2
Square Feet1100-1500 sqft
Fronting OnWest
Dir/Cross St4th Line / Rebecca St
Garage TypeAttached
Garage Parking Spaces4
DrivePrivate
Parking Drive Spaces6
Total Parking Spaces10
ExteriorStucco (Plaster)
RoofShingles
FoundationUnknown
BasementFinished, Separate Entrance
Fireplace FeaturesYes
Heating TypeForced Air
Heating SourceGas
A/CCentral Air
SewersSewer
Listed Date3/16/2026
Days on Market241 days

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Listing Courtesy of: SUPERSTARS REALTY LTD.

MLS® #W12888432

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.

Thinking about living in Oakville?

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HouseIndex Take: 366 Winston Road

This detached (Bungalow) is located in the 1020 - WO West neighbourhood of Oakville.

The home offers 4+2 bedrooms, 2 bathrooms.

Features include a finished, separate entrance basement, 10 parking spaces including a 4-car garage, a fireplace.

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 →