Leaside has ample parkland, greenspace, outdoor recreation and one of the best shopping districts uptown along Bayview Avenue making it one of the most popular neighbourhoods in Toronto. It is no surprise why Leaside is consistently sought after among move-up buyers and custom home builders. Leaside homes are characterized by larger than normal lots with private drives and garages. The moment you drive through any of the quaint Leaside streets you will see why people love to live here. 



Leaside has been an in-demand neighbourhood for years and the reasons are obvious if you take the time to walk or drive along it’s streets. From the shops along Bayview Avenue to abundant parkland and great schools, the community that has thrived in Leaside is incredibly special. The recreational aspects of the neighbourhood are vast with the Leaside Baseball Association, soccer associations, tennis courts and Serena Gundy Park in North Leaside. Leaside also hosts a variety of pre-school, elementary, and high schools within a short distance which make it a great option for families who want a long-term close-knit community.

Homes in Leaside are situated on generous size lots with private drives and garages. The Tudor-style houses built in Leaside during the 1930’s and 40’s contain beautiful wood trims, hardwood floors and fireplaces. Custom homes or large-scale renovations of old bungalows are becoming more and more prevalent with the rise of home prices in the area. During the 1990’s there were some exclusive apartments and townhomes built on the periphery of the residential streets. Most of these are along the East side of Bayview Avenue and on Leacrest Road overlooking the Don Valley Ravine.


John Lea, a pioneer farmer who emigrated to Canada from Philadelphia in 1819 is Leaside’s namesake. His first home in the rural neighbourhood at the time was situated near what is now Leaside Memorial Gardens. The Canadian Northern Railway incorporated the Town of Leaside in 1913 on land formerly owned by the Lea family. Leaside holds a historically significant place in Ontario’s developmental history. It was the first town in Ontario to be entirely drafted on paper before being built.

World War I stalled the development of the residential portion of the community, but Leaside was incredibly important to the outcome of the war. The Leaside Munitions Company manufactured heavy artillery for the war effort as well as trained Canadian pilots at an airfield nearby the factory. In the final year of World War I Leaside also made Canadian Aviation history by being the landing point of the first airmail flight in Canada from Montreal to Toronto.


James Strathy Warren

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Alexander Obradovich

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