This is the heart of the town. When people dream of "Oakville," this is usually what they are picturing: the boutique shops on Lakeshore, the sailboats in the harbour, and homes that have stood for a century.
Old Oakville (often overlapping with Southeast Oakville) is unmatched in character. It is the only place where you can find a 1800s heritage cottage right next door to a modern, custom-built masterpiece.
The Real Estate Landscape
Real estate here is diverse but generally commands a premium price per square foot due to the land value.
- Heritage Homes: South of Lakeshore and near the downtown core, you find designated heritage properties. These are stunning but require a Realtor who understands heritage permits and renovation restrictions.
- The "Gold Coast": Along Lakeshore Road East and the streets running down to the lake, you will find some of the most expensive real estate in Canada. Massive lots, private gates, and lake views.
- Luxury Townhomes: Near the library and the harbour, there are high-end townhomes perfect for downsizers who want to walk to dinner.
🛒 The Walkable Lifestyle
The biggest perk here is the lifestyle. You can leave the car in the driveway. You are steps away from high-end dining like Hexagon or Oliver's, coffee at Tribeca, and browsing the boutiques. The Oakville Harbour is your backyard.
Schools
Education is a major draw. Oakville Trafalgar High School (OT) is legendary for its academics. You also have easy access to top private schools like St. Mildred's-Lightbourn (girls) and Linbrook (boys), as well as MacLachlan College right on Trafalgar.
Transit & Connectivity
While it feels like a village, it’s incredibly well-connected. The Oakville GO Station is the main hub—you can get express trains to Union Station in about 30 minutes. It is the preferred neighbourhood for Bay Street executives who want the cottage feel without the cottage commute.
Why Choose Old Oakville?
It’s about prestige and charm. There is a sense of history here that you cannot replicate in the suburbs. Whether it’s the Jazz Festival in the summer or the tree lighting in the square at Christmas, there is a true sense of community.
Explore Old Oakville
Navigating the heritage districts and custom home market in Old Oakville requires local expertise. Let's discuss your vision.