Leaside Neighbourhood Guide: History, Homes, and Why People Stay
Welcome to the first post in a new series where I’ll be highlighting some of Toronto’s most interesting and sought-after neighbourhoods — exploring their history, homes, and what makes them unique places to live.
I’m starting with Leaside — not just because it’s one of the city’s most established and family-friendly areas, but because it’s where I grew up. I know the streets, the parks, the routines, and the ways this neighbourhood has grown while still holding onto its identity. Whether you're just getting to know Toronto or have lived here for years, Leaside offers a mix of character and consistency that’s hard to ignore.
A Look Back: The History That Shaped Leaside
Long before it became one of Toronto’s most sought-after neighbourhoods, Leaside was a carefully planned community with deep roots in industry, transportation, and local pride.
The area takes its name from the Leaside family, particularly John Lea, who immigrated from England and settled in the region in the early 1800s. His son, William Lea, built the family home near what is now Bayview and Eglinton, and the name “Leaside” came from their stone house, Leaside Manor.
But it wasn’t until the early 1900s that Leaside began to take real shape. The Canadian Northern Railway selected Leaside as the site for a major railway and industrial hub. In 1913, the area was officially incorporated as the Town of Leaside, with a vision of being a modern, self-contained suburb — one of Canada’s first planned communities.
Throughout the 1920s and 1930s, residential growth expanded along key streets like Bessborough Drive, Laird Drive, and Hanna Road, where many of the classic brick homes still stand today. The area was filled with detached homes, generous lots, and a village-like layout, all of which remain part of Leaside’s charm.
Leaside also played a role in Canada’s military history — De Havilland Aircraft Company operated a major aircraft manufacturing facility on Wicksteed Avenue during World War II, producing the Mosquito bomber aircraft. This industrial past helped fuel employment and economic growth, shaping the community around it.
After being amalgamated into the City of Toronto in 1967, Leaside retained its identity through local institutions like Trace Manes Park, the Leaside Library, and the Leaside Memorial Community Gardens, a beloved hockey and recreation hub that continues to serve generations of local families.
Today, you can still feel that small-town legacy — from the post-war homes lining Fleming Crescent to the locally owned shops along Bayview Avenue. It’s that rare blend of heritage and livability that continues to make Leaside one of Toronto’s most enduring and respected neighbourhoods
How Leaside’s Housing Market Has Evolved
Leaside’s housing market has been shaped by a combination of thoughtful planning, generational ownership, and growing demand — all of which have helped it hold its value and prestige through market ups and downs.
In the mid-20th century, most of Leaside’s homes were built as solid, functional single-family houses — modest in size by today’s standards, but known for quality craftsmanship. These homes, especially those along Bessborough Drive, Parkhurst Boulevard, and Rykert Crescent, became staples of the east-end housing stock.
By the 1990s and early 2000s, Leaside began to shift. The neighbourhood’s appeal to families — especially those looking to trade up from condos or starter homes — drove demand higher. As property values in central Toronto surged, Leaside’s quiet streets and access to top-tier schools made it a natural move-up destination. Many original homeowners either stayed put or passed homes down to family, which kept inventory tight and prices rising steadily.
The early 2010s brought another transformation: new-build custom homes and major renovations began to replace original bungalows and wartime homes. It’s common now to see large, modern houses on lots that once held compact post-war dwellings — particularly near Hanna Road, Sutherland Drive, and Randolph Road. These new builds helped raise the overall price benchmark for the neighbourhood and attracted a new generation of affluent buyers.
In more recent years, the development of the Eglinton Crosstown LRT has continued to shape demand. Although delayed, its eventual opening will give Leaside faster, direct transit access across the city — a huge value-add for both homeowners and investors.
Despite broader market shifts across Toronto, Leaside has shown remarkable stability. Homes tend to sell quickly when priced properly, and the community remains a magnet for buyers looking for long-term value and a strong sense of place. What’s changed over the decades is not just the pricing — but also the expectations. Today’s buyers are looking for move-in-ready homes, thoughtful renovations, and proximity to both downtown and green space.
Why People Stay in Leaside (And What Keeps Them Here)
Ask most people who live in Leaside how long they’ve been there, and the answer usually isn’t months — it’s decades. This is the kind of neighbourhood where families grow up, kids walk to school just down the block, and people find very little reason to leave. It’s not just about location — it’s about rhythm, routine, and community.
One of the biggest anchors is the school system, with several well-regarded public schools serving the area:
Bessborough Drive Elementary and Middle School
Rolph Road Elementary School
Northlea Elementary and Middle School (offering French immersion)
Leaside High School
For many families, the ability to walk to these schools is a huge part of why they stay rooted here long term.
Beyond the classroom, Leaside’s lifestyle offers even more reasons to stay:
Leaside Memorial Community Gardens — home to house league hockey, skating programs, and a community pool
Trace Manes Park — a family hub with baseball diamonds, tennis courts, and a playground
House league baseball — a longtime neighbourhood tradition each spring and summer
Bayview Avenue — lined with local bakeries, cafés, flower shops, and small businesses that residents grow up loving
There’s also a strong sense of community through seasonal events, rec leagues, and an active neighbourhood association. Even as the homes evolve — through renovations or rebuilds — the heart of the area remains the same: a place where people settle in and stay for the long haul.
Final Thoughts: Why Leaside Still Feels Like Home
Leaside has changed in a lot of ways over the years — but at its core, it’s still the same tight-knit, proudly local neighbourhood I grew up in. I was lucky to experience everything it has to offer: the schools, the parks, the hockey games, and the sense of community that makes this place feel like more than just a collection of homes.
That personal connection is what makes helping clients buy or sell here so meaningful for me. It’s not just about square footage or pricing strategy — it’s about understanding the rhythms of a neighbourhood, the value of its streets, and the lifestyle that comes with it.
Whether you’re considering a move to Leaside or just starting to explore what Toronto has to offer, I’m always happy to share what I know — no pressure, just honest insight from someone who’s seen this community grow from the inside out.
Need Advice? I’m Here to Help.
If you’re curious about how things are moving in your specific area — or you just want to talk strategy — feel free to reach out anytime. Whether you're ready to jump in or just gathering info, I'm happy to help you make sense of the market.
