Leaside

Leaside stands out as one of Toronto’s most coveted neighborhoods. Given its high profile, it's not surprising that real estate here comes at a premium. This neighborhood is particularly favored by upper-middle-income families who see it as an ideal place to raise children. Leaside boasts ample green space and parkland, a fine selection of schools, one of Toronto’s best shopping districts on Bayview Avenue, and excellent access to public transit.

History

Leaside's origins trace back to John Lea, a pioneer farmer who emigrated from Philadelphia to Canada in 1819. In the 1850s, Lea’s eldest son, William, constructed an octagonal house aptly named 'Leaside' near the present-day site of Leaside Memorial Gardens, giving the neighborhood its name. The Canadian Northern Railway established the Town of Leaside in 1913 on land previously owned by the Lea family. Notably, Leaside was the first town in Ontario to be fully planned on paper before any homes were built. Although residential development slowed due to World War I, Leaside played a crucial role in the war effort, manufacturing heavy artillery at the Leaside Munitions Company and training Canadian pilots at its airfield. In 1918, the Leaside Airfield marked a milestone in Canadian aviation history as the terminus of the first airmail flight in Canada from Montreal to Toronto. Leaside retained its town status until 1967 when it became part of the Borough of East York, which later amalgamated with the City of Toronto.

    • North: Don River

    • East: Canadian Pacific Railway

    • South: Canadian Pacific  Railway

    • West: Bayview Ave

  • Typical Leaside homes sit on large lots with private drives and garages. Many feature beautiful wood trim, hardwood floors, and working fireplaces. Built mainly in the 1930s and 1940s, Leaside’s Tudor-style houses include a mix of two-storey detached homes, bungalows, and semi-detached houses. Over the years, numerous bungalows have been expanded with second-storey additions or replaced by new custom-built homes.In the 1990s, a few exclusive condominium and townhouse projects began to emerge in the neighborhood. Leaside also hosts some of Toronto’s nicest rental apartment buildings, especially on the east side of Bayview Avenue and on Leacrest Road overlooking the Don Valley Ravine.

    • K-6

      • Rolph Road Elementary School

      • Bennington Heights Elementary School

    • K-8

      • Bessborough Drive Elementary and Middle School

      • Northlea Elementary and Middle School

      • St. Anselm Catholic School

    • Grade 9-12

      • Leaside High School

  • In 1918, Leaside was the site of Canada Post’s first airmail delivery, when 120 letters were received from Montreal via airplane to the neighbourhood’s local post office.

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