Living in Leaside
Leaside is one of the only neighbourhoods in Ontario that was a family neighbourhood before it was anything else — planned that way on paper in 1913, then filled in with the Tudor-style homes that still line its streets. It’s also the rare Toronto neighbourhood whose biggest change in decades just happened: the Eglinton Crosstown opened right along its northern edge in February 2026.
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A Town Planned Before a Single House Existed
Most neighbourhoods grow into their character. Leaside was handed one on day one: incorporated in 1913, it was the first town in Ontario ever laid out completely on paper — streets, lots and all — before a single home was built, designed by landscape architect Frederick Todd for a subsidiary of the Canadian Northern Railway. The houses came through the 1930s and 40s, mostly Tudor-style detached and semi-detached homes, and the plan is still doing exactly what it was built to do.
About 49% of Leaside’s households today are families with children — one of the highest shares anywhere in central Toronto — and the neighbourhood still runs on school schedules, hockey practice, and the Saturday walk down to Bayview Avenue.
From Farmland to a Company Town
Before it was a town, it was the Lea family’s farm — settled in the early 1800s, and farmland for most of the century that followed. The name comes from Leaside Junction, a rail stop named for the Leas’ octagonal farmhouse. When the Canadian Northern Railway needed a planned community to support its rail yards, that farmland became the site, and on April 23, 1913, the Town of Leaside was incorporated with a population of 43.
It stayed its own town for over fifty years. In 1967, Leaside amalgamated with the Township of East York to form the Borough of East York, and in 1998, East York — along with the rest of old Metro Toronto — became part of the amalgamated City of Toronto.
Some of my favourite Leaside streets are the quiet, tree-lined ones where you get a real sense of the neighbourhood’s history. The streets feel established and residential, but you’re still close to the shops, schools, parks and transit that make Leaside so convenient.
Quiet South, Connected North
Leaside isn’t one commute or one pace of life — it splits roughly in two along how close a street sits to Eglinton. The Crosstown’s arrival made that split sharper than it used to be.
South of Leaside is great — Airdrie Road and Sutherland Drive are very quiet and family-oriented, but you’re further from the subway. Streets closer to Eglinton have a better commute and are closer to the amenities on Bayview and Laird.
Neither side is the “wrong” choice — it’s a genuine trade-off between the calmest, most established family streets and the shortest walk to a station and a coffee shop. Worth working through with a buyer before a specific street gets ruled in or out.
Real Recreation, Not Just a Park Sign
Leaside Memorial Community Gardens, at Millwood and Laird, is the neighbourhood’s institution — twin ice pads, an indoor pool and a curling rink, with generations of Leasiders having learned to skate there. Trace Manes Park, off McRae Drive, is home to the Leaside Tennis Club’s six courts along with a playground, a baseball diamond and a winter rink, with the Leaside branch of the Toronto Public Library right next door. Howard Talbot Park, at Bayview and Eglinton on the neighbourhood’s northwest edge, covers two more baseball diamonds and a splash pad.
On the eastern edge, the ravine system takes over: Serena Gundy Park runs 62.6 acres in the northeast corner, connecting through to Sunnybrook Park and the Don trail system. It’s suburb-calm streets with a genuine wilderness exit a few minutes’ walk away.
The Schools Are the Market
No honest Leaside page can bury this: schools drive this market. Families buy in specifically for the catchments and hold on for a decade or more — a large part of why inventory stays tight and values hold. As always, catchments change — verify with the TDSB before an offer rests on one.
305 Rumsey Rd · JK–8
211 Bessborough Dr · JK–8
31 Rolph Rd · JK–6
76 Bennington Heights Dr · JK–6
200 Hanna Rd · Grades 9–12
182 Bessborough Dr · JK–8
A Main Street, and Finally a Subway
The Bayview Leaside BIA runs from Davisville to Soudan — specialty shops like Cumbrae’s (butcher) and Alex Farm Products (cheese), restaurants and cafés with strollers parked two-deep. A block over on Laird, Olde Yorke Fish & Chips has been serving the neighbourhood for 20-plus years, and LOCAL Public Eatery occupies a converted 1940 bank building with two floors and a rooftop patio. Leaside Village, at Laird and Esandar, adds the anchor stores: 120,000 square feet built around a Longo’s in a heritage 1919 railway building, alongside Linen Chest, Amsterdam Barrel House, PetSmart and Shoppers Drug Mart. Everyday life happens on foot here, which is rarer than it should be in a neighbourhood of driveways and garages.
Leaside’s historic weak spot — transit — is the thing that just changed. The Eglinton Crosstown (Line 5) opened on February 8, 2026, running along the neighbourhood’s northern edge with Leaside station (at Bayview) and Laird station, connecting Leaside into the rail network it never had. Drivers are minutes from the DVP via Millwood or Eglinton.
Leaside has a way of feeling established without feeling stuck in the past. I love the combination of mature streets, character homes and easy access to the Eglinton Crosstown — it’s now one of the reasons buyers love it even more.
What Leaside Actually Sells For
Through September 2026, 79 detached homes have sold in Leaside this year. Nearly half — 35 of them — sold under $2 million, with the least expensive going for just over $1 million and a typical 30-foot lot landing around $1.3 million. At the top end, the year’s two priciest detached sales were $6.75 million and $4.6 million.
Semi-detached sales this year have ranged from $960,000 up to $2.1 million. Condos remain the minority option here by a wide margin — just 22 condo apartments sold across all of Leaside in 2026, reflecting how little of that stock actually exists in the neighbourhood.
Who’s Buying
About 49% of Leaside households are families with children — the number that explains almost everything else about how this market behaves: low turnover, long hold periods, and prices that lean on catchments as much as square footage.
Leaside Toronto — Your Questions, Answered
About the Neighbourhood
Buying Into Leaside
Thinking About Leaside?
South Leaside or the Eglinton edge, semi or detached, catchment or condo — the right answer depends on what you actually need day to day. Let’s talk it through.
No hard sell. No pressure. Just honest answers.
Cag Icer, Sales Representative · Zolo Realty Brokerage · Licensed in Ontario (RECO #5035461)
Serving Leaside, Toronto, and the Greater Toronto Area.