The present day Leaside Memorial Gardens marks the area where the son of John Lea, pioneer farmer from Philadelphia, built an octagonal shaped house in the 1850s. This neighbourhood has been called Leaside ever since. In 1913, the Canadian Northern Railway incorporated the land owned by the Lea family into the Town of Leaside. This is the first town in Ontario which was completely planned on paper before any of the home were actually built. The outbreak of World War I stalled the residential development of Leaside, but the town was quite useful as it was the place where heavy artillery was manufactured. This was also the location used for training Canadian pilots. In 1967 Leaside became part of the Borough of East York which then amalgamated with the City of Toronto.

Today Leaside is one of Toronto's most popular neighbourhoods, and also one of the most expensive. Middle to High income families see this location as an ideal place to raise children with lots of parkland, great schools, and one of the best shopping districts, the Bayview Avenue. Leaside's new shopping destination is the Leaside Centre, and right across it is the Leaside Business Park which contains a mix of specialty retail stores with light industrial businesses. You will also find many antique shops, and pubs. In terms of recreation Leaside can't be compared to other neighbourhoods, as it is in league of its own. The Leaside Memorial Community Gardens is a multi-recreational complex which offers an indoor ice arena, a curling rink, an auditorium, and an indoor swimming pool. In Sunnybrook Park enjoy a horseback ride, or exercise along the fitness trail, and if you are into sports here you will find excellent sports fields. Worth mentioning is also the Serene Gundy Park, the Trace Manes Park, and the Howard Talbot Park. Another benefit of this location is that this neighbourhood is also well connected to the city's public transit.

Here you will find Tudor-style houses, many of these homes were built in the 1930s and 1940s. A good mix of two-storey detached homes, semi-detached houses and bungalows can also be found in this area. Moreover, in the 1990s there were many condominium and townhouse projects. This location also offers some of Toronto's nicest rental apartments. According to the 2014 real estate stats; semi detached homes sold for $675,000 to $950,000. Older detached homes sold for as a high as $1.2 million whereas newer detached homes sold for between $1 - $1.7million. Bungalows typically sold for over $1 million. Lastly, new custom homes in Leaside old for between $1.7 - $2.7 million.

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