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Detached for sale at 366 Winston Road, Oakville - 4 bedroom, 2 bathroom - Photo 1 of 30
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$4,300

366 Winston Rd

Oakville, ON L6L 4W5

366 Winston Rd, Oakville — Listed at $4,300. 4 bedroom, 2 bathroom Bungalow Detached. MLS® W13155292.

4Beds
2Baths
1100-1500sqft
Detached
Bungalow
10Parking
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Description

Experience refined luxury living in the heart of Oakville with this exceptional, fully renovated detached bungalow located at 366 Winston Rd. Blending timeless elegance with modern sophistication, this stunning home features custom architectural additions at both the front and rear, soaring cathedral and cove ceilings, and multiple skylights that fill the grand, open-concept living space with natural light. The gourmet chef's kitchen serves as a true centrepiece, boasting custom maple cabinetry, premium granite countertops, a built-in cooktop, wall oven, travertine flooring, and an elegant skylight overlooking the living area. The thoughtful 2+2 bedroom and 2 bathroom layout features pristine hardwood floors throughout the main level, designer pot lighting, and seamlessly integrated built-in speakers. The finished lower level includes a separate private entrance, offering maximum flexibility for an extended family, a dedicated home workspace, or guest quarters. Adding rare utility to this rental property is an exceptional oversized garage that accommodates up to four vehicles with ample additional storage. Situated in one of Oakville's most prestigious and highly desirable neighbourhoods, this residence places you just minutes from Appleby College, the scenic lakefront, top-tier schools, boutique shopping, and vibrant local amenities. Available immediately, this distinguished home offers an unmatched lifestyle of comfort, elegance, and premium location in perfect harmony.

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 FeaturesNatural Gas
Heating TypeForced Air
Heating SourceGas
A/CCentral Air
SewersSewer
Listed Date5/21/2026
Days on Market175 days
PossessionImmediate

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Listing Courtesy of: SUPERSTARS REALTY LTD.

MLS® #W13155292

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: 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 →