Leaside Neighbourhood | One of Toronto?s most desirable and family-friendly neighbourhoods

This article was originally featured in the 2020 Fall Issue of Invest In Style Magazine


One of Toronto’s most desirable and family-friendly neighbourhoods, Leaside is bounded on the west by one of the city’s most popular shopping districts, along Bayview Avenue, and extends north to the parkland beyond Eglinton Avenue East. Leaside’s eastern border ends just before Leslie Street, along more green space. Close to its southern border, south of Moore Street, a commercial area includes a multi-service recreation centre, bordered by a walkable forest and the Don Parklands. Leaside is only a 10-minute drive to the downtown core, via the Bayview extension.




Leaside was the first Ontario town to be planned on paper before any building began, in the early 1900s. Homes here are set on ample lots along winding, tree-lined streets. Most of the shopping in this neighbourhood is located along Bayview Street, with its mix of ethnic restaurants, boutique clothing and home décor, children’s toys and clothes, art galleries, specialty shops and neighbourhood pubs. Many of these businesses are locally owned and family run. A number of fresh food markets dot Bayview and there’s a Whole Foods grocery store at the north west corner of the neighbourhood. The residential centre of the neighbourhood is well-served by parks, recreation centres, schools and public transit. When completed in 2021, the Eglinton Crosstown LRT will serve the area with three stations.


Leaside homes include two-storey detached, semi-detached, and bungalows, including the hard-to-find craftsman-style bungalows.


While similar to the adjacent neighbourhood to the north west, exclusive Lawrence Park, Leaside has more of a mix of homes. These include two-storey detached, semi-detached, and bungalows, including the hard-to-find craftsman-style bungalow. Most of the homes are Georgian revival and Tudor-style, but a number of the houses on corner lots were built in the Cape Cod style of architecture, with a side entrance, bay window and mix of brick and stone.


The neighbourhood also includes exclusive condominiums and townhouses, from the 1990s, as well as new buildings still under construction. Leaside is also home to some of the nicest apartments in the city, some with views of the Don Valley.


Leaside is home to many local businesses, Bayview Avenue features a wonderful collection of shops, specialty stores, and neighbourhood pubs.


At the south west corner of Eglinton Avenue East and Brentcliffe Road, a new luxury condo development, the Upper East Village, will cover three blocks, centred around a public park. Proposed amenities include a rooftop dining terrace, indoor pool, and fireplace lounge for the limestone, brick, wood and glass buildings, inspired by the Upper East Side neighbourhood of New York.


Leaside is a family-centred neighbourhood with a strong sense of community. Its many parks and green spaces, recreational facilities and good schools serve residents well. In the north east corner of the neighbourhood, Serena Gundy Park offers walking, cycling and cross- country ski trails. And a waterfall! Down a set of wooden steps, a wooden trestle bridge crosses the Don River and leads to the 147-acre Sunnybrook Park, with its off-leash dog area and horse stables.



Trace Manes Park Community Centre offers a variety of programs for families and seniors. Trace Manes Park Community Centre is located near Laird Drive and Eglinton Avenue East. 


In the centre of the neighbourhood, Trace Manes Park Community Centre offers a variety of programs for families and seniors. The park itself includes a baseball diamond, playground, and tennis courts, run by the Leaside Tennis Club. At the north end of the park you’ll find the local branch of the Toronto Public Library. Howard Talbot Park in the south west of the neighbourhood has two baseball diamonds and an outdoor splash park for the little ones.


South east, on Millwood Road, in the commercial area of the neighbourhood, the Leaside Memorial Community Gardens includes ice and curling rinks and an indoor pool. There’s a Home Depot in this area for the DIYers.


Leaside Tennis Club is a very active community tennis club operating in the popular Leaside area of Toronto. Trace Manes Leaside’s family-centred neighbourhood Park, between Rumsey Road and McRae Drive. The six courts are floodlit for evening play and feature “Deco Turf” surface.


On the western border of the neighbourhood, along Bayview, historic Mount Pleasant Cemetery’s expansive green space is home to a botanical garden and is one of the most impressive arboretums in North America. The grounds offer visitors walking and running routes and provide access to Avenue Road on the west side.


There are a number of good schools to choose from throughout the neighbourhood, including a Montessori school, art and music schools, and well- ranked elementary and high schools such as Northlea Elementary and Middle School, Bessborough Drive Elementary, Leaside High School and St. Anselm Catholic School. CGS (Children’s Garden School) is a co-ed, private elementary school (preschool to grade 3) on Eglinton Avenue, just east of Bayview.



Leaside High School was founded in 1945. Leaside continues to maintain a tradition of academic excellence.


There are two hospitals in and near Leaside: Holland Bloorview Kids Rehabilitation Hospital in the north west corner, and Sunnybrook Health Sciences Centre just north of the neighbourhood boundary. Kid- centred Ontario Science Centre is just a few minutes east of Leaside.




The wide variety of Leaside’s family-friendly amenities, including green spaces, recreational facilities and some of the best shopping opportunities in the city, all adjacent to hundreds of acres of walking and biking trails, make this one of Torontos most desirable neighbourhoods.


Written By Lesley Kenny

Photography By Taylor Nullmeyer