All photos courtesy The Fine Estates Team

Just 30 kilometres west of Toronto’s ritzy Yorkville district and 40 minutes from the wine country of Niagara-on-the-Lake, Oakville continues to dominate the Greater Toronto Area luxury real estate market. The community’s peaceful tree-lined streets, its proximity to Lake Ontario, and access to some of Canada‘s highest-rated schools have transformed former farmland into one of the country’s wealthiest municipalities.
The numbers tell the story. Median household incomes here exceed $170,000, nearly double the provincial average. Residents also enjoy 1,400 hectares of parkland, 280 kilometres of walking trails, and a lovely harbourfront area that rivals any in the Golden Horseshoe.

Add direct GO Train service to Union Station in downtown Toronto in just 35 minutes, and it becomes clear why families relocating from places like the UK, Europe, and the United States, also consistently choose Oakville over other GTA communities.
Now, 493 Brookside Drive enters this competitive market with a proposition that goes well beyond simply square footage (and at 4,000 sq ft, that’s something it certainly has plenty of). Newly listed, this immaculate, must-view custom-built Oakville home occupies a quiet spot in the mature South Oakville neighborhood, where century-old oaks shade the streets and properties rarely turn over.
Rare Luxury South Oakville Home for Sale
The home’s 14.5-foot ceilings immediately set the tone upon entry. Coffered detailing in both living and dining rooms recalls traditional estate architecture, while floor-to-ceiling windows flood every corner with natural light. The main floor flows from formal spaces to a chef-caliber kitchen equipped with JennAir professional series appliances, while the waterfall island spans nearly 12 feet, providing both prep space and casual seating for six.

A walk-through servery connects the kitchen directly to the formal dining room, a layout that eliminates the typical bottleneck during dinner parties. Custom cabinetry throughout includes soft-close drawers, pull-out pantry systems, and a built-in coffee station with its own water line.
There’s a main floor office, too, which addresses today’s “work-from-home reality.” Thanks to its own exterior entrance, clients or colleagues can enter directly without having to pass through living spaces, maintaining professional boundaries while eliminating commute time. Built-in shelving, hardwired ethernet connections, and soundproofing make this a legitimate commercial-grade workspace.
GTA Living at its Best
Upstairs, a skylight illuminates the central hallway, reducing the need for artificial lighting during daylight hours. Each of the four upper bedrooms includes its own ensuite bathroom, eliminating morning conflicts and providing hotel-like privacy for teenagers or guests. The huge primary suite occupies the entire rear portion of the second floor, with a walk-in closet that features its own skylight and custom organizer systems from California Closets.

You’ll find the primary bathroom rivals any spa with its freestanding soaker tub, dual-entry glass shower with rainfall and handheld fixtures, along with a double vanity topped with Caesarstone quartz. Heated floors are timer-activated, ensuring warm tiles for those early starts.
The 2,000-square-foot finished basement adds countless other entertainment possibilities with its custom bar with a Sub-Zero beverage fridge, dishwasher, and granite countertops. The open-concept media area accommodates a 75-inch television with surround sound wiring already in place, while a fifth bedroom and full bathroom create options for live-in help, elderly parents, or returning kids.
Posh Living in Oakville
From the kitchen’s west-facing windows, the backyard reveals its centerpiece: a brand-new saltwater pool complete with cascading water features and LED lighting systems.

The outdoor space also eliminates maintenance headaches through the clever use of artificial turf that stays green year-round without watering or cutting being necessary, while the walk-up access from the basement to the backyard means pool parties flow naturally between indoor and outdoor spaces.
But the property’s most unusual feature (it’s certainly an appealing one) might be the gated access directly to the adjacent municipal park. This private entrance transforms public green space into an extension of the backyard, essentially adding acres of maintained parkland for morning runs or evening strolls.
Location, Location, Location
Location-wise, the property sits within the catchment for Sunningdale Public School and White Oaks Secondary School, both ranking in Fraser Institute’s top tier of educational institutions. If you’d prefer to go the private route, the now co-ed Appleby College and the all-girls St Mildred’s-Lightbourn School could be just the ticket your kids need to a successful future.

If higher education is on the radar, Sheridan College‘s Trafalgar Campus is an easy 10-minute drive, while both McMaster and the University of Toronto campuses are accessible via GO Train connections from the nearby Oakville GO station.
You’ll find your shopping needs met at Oakville Place, while golf enthusiasts will want to play at Glen Abbey, just five minutes north of town. ClubLink‘s Hidden Lake Golf Club course is equally close. For aviation enthusiasts or those wanting to fly north to Muskoka, nearby Burlington Airpark accommodates private aviation for those weekend cottage escapes.
Fast Facts & Fast FAQs
Need to know more about this luxury South Oakville home for sale? Here’s the scoop:
- Location: 493 Brookside Drive, Oakville, ON
- Listed for sale by Ashtonne Tesoro, Salesperson, The Fine Estates Team, Revel Realty Inc.
- House Type: 4,000 sq ft custom-built two-storey detached
- Bedrooms: 4+1
- Bathrooms: 6
- Garages: Information not provided in listing
- Price: $3,750,000
- MLS#: W12416428
Interested in learning more? Check out the full listing for this luxury South Oakville home for sale by clicking here.
______________________
Bryan Dearsley is an Ontario-based writer and is Editor of LuxuryOntario and LuxuryOakville.