Our City Spotlight  series explores the neighbourhoods that make up Toronto and the GTA. Each month, we take a look at what makes these areas unique and what we love most about them. Join the discussion on our social media and share your favourite things about each neighbourhood we feature!



Located northeast of the downtown core in the midtown area of Toronto, Leaside is one of the most popular and desirable neighbourhoods in the city. 

Its expansive greenspace and parkland, excellent recreational facilities, a selection of top-notch schools, the fantastic shopping districts on Bayview Avenue, and easy access to public transit lend to its appeal. The neighbourhood has attracted young and growing families for decades, and offers homeowners the potential for an excellent return on their investment. 

The typical Leaside home has a large lot with a private drive and a garage. Leaside's Tudor-style houses were built largely in the 1930's and 1940's. The neighbourhood features a good mix of two-storey brick 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 A growing number of Leaside bungalows have had second storey additions, while others have been replaced by new custom designed homes.

Many of the houses in Leaside share definitive architectural characteristics, including prominent front bay windows, arched entryways accentuated with cut stone, and wide door casings made of hand-crafted wood. Intricate stonework, etched dentil, artisan mouldings and patterned masonry are among the other common design elements of Leaside homes. The average lot size is 32 feet by 125 feet, and virtually all the neighbourhood’s homes have their own private driveways. According to the North Toronto Post, Bessborough Drive is the neighbourhood’s best street, offering wide, majestic boulevards, mature trees and grand homes with historic dignity.


Fun Facts

  • The neighbourhood takes its name from William Lea and the Lea family, who settled there in the early years of the 19th century. 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.
  • The district made important contributions to the Canadian war effort during World War I, as the Leaside Munitions Company was an important manufacturer of heavy artillery. Leaside was also the location of an airfield used for the training of Canadian pilots.
  • Leaside was the site of the first airmail delivery in Canada Post history, when 120 letters sent from Montreal were delivered via airplane to the local post office in 1918.
  • The intersection of Bayview and Eglinton was also home to Toronto’s first strip mall, known as Sunnybrook Plaza.
  • Over the years, many luminaries and prominent citizens have called Leaside home. Prime Minister Stephen Harper was born in Leaside, and former Toronto Maple Leafs players Darcy Tucker and Doug Gilmour also live in the neighbourhood. Former NHL player and current Sportsnet hockey analyst Nick Kypreos is another well-known Leaside resident.


Future Outlook

The development of the Eglinton Crosstown LRT will provide visitors and residents with even better access to the transit system and an easier commute to the Yonge Street corridor and the downtown core. Along with the recent addition of the Leaside Smartcentre off of Laird Drive with its many big-box stores, and with the near and future completion of several prominent condominium developments in the area, property values are sure to appreciate at an even greater rate, so buying in this neighbourhood is certainly a solid investment! 


Cool places to check out in Leaside