362 Winston Road, photo 1

For sale West, Oakville, ON

362 Winston Road

List price
$1,799,900
Sq ft
2000-2500
Bedrooms
3
Bathrooms
4

About this home

Welcome to 362 Winston Road, a sophisticated South Oakville residence situated on a coveted street surrounded by custom multimillion-dollar homes, and walking distance from Appleby College. This deceptively large, renovated bungalow features an amazing, multi-level rear addition that dramatically expands its square footage and provides distinct, functional living zones. The heart of the addition is a spacious ground-floor family room with a gas fireplace, large windows, and a direct walk-out to a private, west-facing backyard. Positioned on its own dedicated upper level, the expansive primary bedroom retreat serves as a private sanctuary complete with a sitting area, skylight, generous closet space, and a 5-piece ensuite. The original main level accommodates daily living with hardwood floors, solid wood California shutters, an updated skylit kitchen, a breakfast nook, a formal dining room, two additional bedrooms, and a 4-piece bathroom. The home's footprint extends into a fully finished lower level, significantly increasing functional space with a large recreation room, home office, gym, laundry area, full 3-piece bathroom, and extensive storage. With four full bathrooms distributed throughout, the layout effortlessly accommodates families and guests. Externally, the property features a rare, oversized attached four-car garage and mature landscaping. This property offers a rare blend of space, privacy, and location in one of South Oakville's premier enclaves.

Photos of 362 Winston Road

Facts and features of 362 Winston Road

Key facts
TypeDetached
StyleBungalow
Bedrooms3
Bathrooms4
Size2000-2500 sq ft
Lot75.13 x 155.94 Feet
Parking8
GarageAttached
HeatingForced Air
CoolingCentral Air
BasementCrawl Space, Full, Unfinished, Finished
ExteriorStucco (Plaster)
Age51-99
Taxes$9,004 (2026)
Days on market4
Listing brokerageRoyal LePage Realty Plus Oakville, Brokerage

Rooms

17 rooms, with sizes

RoomLevelSizeFeatures
Bedroom 2 Main 13′ 7″ × 11′ 3″
Bathroom Ground 10′ 8″ × 5′ 1″ 3 Pc Bath
Bathroom Main 6′ 6″ × 4′ 11″ 4 Pc Bath
Dining Room Main 16′ 3″ × 7′ 8″
Recreation Basement 14′ 6″ × 10′ 8″
Bathroom Second 11′ 1″ × 5′ 0″ 5 Pc Ensuite
Laundry Basement 26′ 11″ × 8′ 0″
Breakfast Main 12′ 0″ × 8′ 9″
Family Room Ground 17′ 4″ × 15′ 7″
Kitchen Main 11′ 8″ × 9′ 8″
Bathroom Basement 6′ 6″ × 6′ 1″ 3 Pc Bath
Primary Bedroom Second 21′ 1″ × 19′ 4″
Office Basement 11′ 7″ × 10′ 8″
Bedroom 3 Main 13′ 7″ × 9′ 0″
Living Room Main 15′ 4″ × 9′ 10″
Den Basement 14′ 10″ × 10′ 8″
Other Main 8′ 11″ × 4′ 1″

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MLS® W14117948 Data source: PropTx Listed October 26, 2026