Leaside was first settled by John Lea a pioneer farmer who emigrated to Canada from Philadelphia in 1819. In the 1850's, Lea's oldest son William built an eight-sided octagonal shaped house - appropriately named 'Leaside' - near the present day site of Leaside Memorial Gardens. This neighbourhood has been called Leaside ever since.
The Canadian Northern Railway incorporated the Town of Leaside in 1913 on land formerly owned by the Lea family. Leaside's development was historically significant in that it was the first town in Ontario to be completely planned on paper before any homes were actually built.
Leaside's residential development was stalled due to the outbreak of World War I, however Leaside was an important contributor to the war effort. Heavy artillery was manufactured at the Leaside Munitions Company. Leaside was also the location of an airfield used for the training of Canadian pilots.
In 1918 the Leaside Airfield made Canadian aviation history as the terminus of the first airmail flight in Canada, travelling from Montreal to Toronto. Leaside's status as a Town came to an end in 1967 when it became part of the Borough of East York, which has since amalgamated with the City of Toronto.
Leaside is one of the most popular neighbourhoods in Toronto. In light of its high profile, it is not surprising that Leaside is also one of the more expensive real estate districts in Toronto.
Leaside is in especially high demand with upper middle income families who value this neighbourhood as an ideal place to raise children. Leaside has abundant greenspace and parkland, a fine selection of schools, one of Toronto's best shopping districts on Bayview Avenue, and excellent access to public transit.
The typical Leaside house is situated on a generous size lot with a private drive and a garage. Most of the houses contain beautiful wood trim, hardwood floors and a working fireplace.
Leaside's Tudor-style houses were built largely in the 1930's and 1940's. There is a good mix of two-storey detached homes, bungalows and semi-detached houses. A growing number of Leaside bungalows have had second storey additions, while others have been replaced by new custom designed homes.
During the 1990's a handful of exclusive condominium and townhouse projects have been built on the periphery of the neighbourhood. Leaside also contains some of Toronto's nicest rental apartment buildings, located on the east side of Bayview Avenue and on Leacrest Road overlooking the Don Valley Ravine.
(P) Bessborough Drive Elementary & Middle School, 211 Bessborough Drive, (416) 396-2315
(P) Northlea Elementary & Middle School, 305 Rumsey Road, (416) 396-2395
(P) Rolph Road Elementary School, 31 Rolph Road, (416) 396-2435
(PH) Leaside High School, 200 Hanna Road, (416) 396-2380
(CA) St. Anselm Catholic Elementary, 770 Millwood Road, (416) 393-5243
(PR) The Junior Academy, 235 McRae Drive, (416) 425-4567
(PR) Crescent School, 2365 Bayview Avenue, (416) 449-2556
(PR) Childrens Garden Nursery School, 1847 Bayview Avenue, (416) 488-4298