Leaside is between Bayiew and a bend in the Don River, and has some of the most expensive real estate in Toronto for its access to recreation, shopping, and transit. The area was settled by American immigrant farmer John Lea in 1819, and his son built an 1850 octagonal house he named 'Leaside' and the name has stuck. The Town of Leaside was planned and incorporated by the Canadian Northern Railway on land acquired from the Lea family, to build the first fully pre-planned community in Ontario, with industrial areas east of Laird, and homes to the west. During World War I, the community was the location of heavy artillery plant and a training airfield. After the war, residential development continued. In 1967, Leaside was amalgamated into East York, which in 1999 became part of Toronto. To the north of Leaside is the Sunnybrook Health Science Centre and the Lyndhurst Hospital.
Motorists get to downtown in 10 minutes via the Bayview extension and can access the 401 via the Don Valley Parkway. TTC offers a community bus to the St. Clair subway station. and an Eglinton Avenue bus that connect to the Eglinton station on the Yonge-University-Spadina subway line.
The community is served by 2 elementary schools, 2 Catholic elementary schools, 2 public high schools, and 2 private schools,. Nearby colleges includes De La Salle College on Avenue Road at Farnham, George Brown College just south of Davenport, St Michael's College nearby at Bathurst & St Clair. University of Toronto is accessed via the Bloor-Danforth subway, and York University's Glendon Campus just north on Bayview Rd
Bayview Avenue, south of Eglinton, has a compact shopping district with a mix of good shops and restaurants. There are also a number of plazas and malls along Eglinton, including Sunnybrook Plaza (at Bayview), Leaside Centre (at Laird Drive), and the East York Town Center is just east on OverleaBoulevard.
To the north of Leaside is the West Don River valley and Sunnybrook Park, with numerous sports fields, horseback stables & equestrian trails, and nature trails that continue north to the very pretty Edwards Gardens and the Toronto Botanical Gardens, adjacent to the luxury community of Bridal Path. The community has several modest parks with playgrounds, 1 indoor pool, 1 ice arena, 1 outdoor ink, 1 curling rink, 6 tennis courts, 3 baseball diamonds, and a community center with auditorium.
Most Leaside homes were built in the 193s and 40s on good size lots with driveways. Those houses are typically Tudor style 2-storey, bungalow and semi-detached models. The area has a number of newer custom-built homes. Over the 1990s, a number of valley-view rental apartments were built along Leacrest Road, east of Bayview. Prices in the community range from low to high-medium.