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.
362 Winston Rd. Oakville On L6l 4w5 is located in Oakville, ON (L6L 4W5).
362 Winston Rd. Oakville On L6l 4w5 is listed for sale at $1,799,900.
This detached home offers 3 bedrooms and 4 bathrooms.
It is a detached home.
Annual property taxes are approximately $9,004 (2026).
Yes — 362 Winston Rd. Oakville On L6l 4w5 includes 8 parking spaces.
Contact Barbara Beers and the Barbara Beers Real Estate team at +1-905-634-2335 or barbara@barbarabeers.com to book a private showing or request more details.

Royal LePage Burloak Real Estate Services
Purchase Price
Estimate only. Does not include property taxes, insurance, or fees. Actual rates may vary. Contact us for personalized mortgage guidance.
Listing Brokerage: Royal LePage Realty Plus Oakville, Brokerage
Advertised By: Royal LePage® Burloak Real Estate Services
MLS®, REALTOR®, and associated logos are trademarks of CREA.
362 Winston Rd. Oakville On L6l 4w5, Oakville, ON, L6L 4W5
City: Oakville
Price: $1,499,900 - $2,099,900
Type: Residential
Bedrooms: 3+
Bathrooms: 4+