304 Winston Road, Oakville, ON L6L4W5




Property Overview
- Detached Home Type
- House Building Type
- 12551 Sqft Lot Size
- NoneCommunity
- 5 Beds
- 6 Full Baths
- Air Conditioning (Central) Cooling
- 0 Half Baths
- 8 Parking Space(s)
- 2026 Year Built
- — Property Taxes
- 100 days Days on Market
- W13159190 MLS® #
- $1,228 Price / Sqft
- Two Storey Style
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Description
Welcome to 304 Winston Rd, an exceptional custom-designed and built residence offering 5897 sq ft of total living space in one of Oakville's most prestigious neighbourhoods. Perfectly positioned on a premium lot just a few minutes walk to Appleby College, this spectacular home blends timeless transitional architecture with sophisticated finishes, modern smart-home technology, and luxurious resort-inspired living.The exceptional backyard is an outdoor retreat featuring custom infinity edge saltwater pool and hot tub surrounded by expansive entertaining areas. Enjoy indoor-outdoor living beneath the covered rear porch complete with built-in automated screens, fireplace and TV allowing for enjoyment well into the shoulder seasons. Integrated security cameras, advanced Control4 automation, and a dedicated Generator provide added convenience, comfort, and peace of mind. Inside, the home exudes warmth and sophistication. The thoughtfully designed layout offers exceptional versatility, highlighted by a rare main floor primary complete with a luxurious ensuite bath and walk-in closet. An integrated elevator provides ease with access to all levels of the home. With 4+1 bedrooms and 5.5 baths, the residence is perfectly suited for families of all sizes. Two separate laundry rooms further enhance the home's everyday practicality and convenience. The fully finished lower level has been meticulously designed for year-round enjoyment featuring radiant heated floors throughout for exceptional comfort. This impressive space includes a home theatre, gym, rec area, guest/nanny suite & ample storage. Combining luxurious amenities, timeless design, and an unbeatable South Oakville location close to top-ranked schools, parks, waterfront trails, and everyday conveniences, 304 Winston Rd. presents an extraordinary opportunity to experience refined custom living in one of the town's most sought-after communities.
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Data is supplied by the Toronto Regional Real Estate Board (TRREB) MLS® System. TRREB is the owner of the copyright in its MLS® System. Data is deemed reliable but is not guaranteed accurate by TRREB. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by The Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA. Used under license.
Data was last updated Friday, August 28, 2026, 2:38:44 PM UTC.







































