When I first met this family, they were planning to leave the city.
With two school-aged children and a need for more space, they had their sights set on Oakville—newer homes, top-ranked schools, and the idea of a quieter life.
But after touring a few properties and comparing options, they started to feel uncertain. What they thought they wanted—space, affordability, and better schools—suddenly didn’t seem so simple.
By the end of our time together, they had bought a detached home in Leaside. Here’s what changed—and why they now say they couldn’t imagine living anywhere else.
They Started with the “Obvious” Choice: Oakville
Like many families, they assumed Oakville would offer a better return: more space, lower prices per square foot, good schools, and a more suburban pace.
But after several showings, they realized:
- School zones were good, but the commute to downtown was long
- Their daily routine would depend entirely on driving
- The sense of community felt less immediate and less integrated
- The idea of returning to the city for activities and social ties felt exhausting
It wasn’t that Oakville wasn’t beautiful—it just didn’t feel like them.
Then We Walked Through Leaside
They agreed to explore Leaside “just to compare.” And that changed everything.
The first thing they noticed? It felt familiar. Comfortable. Human-scaled.
The streets were quiet, the schools walkable, and everything from the hockey rink to the bakery was around the corner.
We visited homes near Bessborough Drive Elementary and Leaside High School—schools known not just for academics, but for their deep community roots. We toured a detached home with a modest backyard, modern kitchen, and quick access to Bayview shops and the future Crosstown LRT.
It wasn’t bigger than what they saw in Oakville. But it made more sense.
What They Gained by Staying in the City
After the purchase, we sat down to reflect. They said three things stood out:
- “We can walk everywhere again.” Their children walk to school, and they rarely need the car.
- “The city still works for us.” One parent works in finance and the other part-time in education. Commutes are simple.
- “We didn’t give up anything that mattered.” Instead, they gained a stronger community, smart resale value, and daily convenience.
What started as a plan to leave Toronto ended with a better life inside it.
Final Thoughts
If you’re comparing neighbourhoods like Oakville and Leaside, there’s no universal answer.
But your lifestyle, commute, school needs, and long-term plans deserve more than a surface-level comparison.
I help families explore both sides of the decision—suburban and urban—until they land somewhere that actually supports how they live.
Send an email at olena@agentolena.com or call 647.294.3039 to get started.
