Toronto's first planned town, Leaside-Bennington delivers prestigious east-end living with top-ranked schools, 147-acre Sunnybrook Park, boutique Bayview Avenue shopping, and the coming Eglinton Crosstown LRT.
Highly educated professional families, top-ranked schools, prestigious village-style community, exceptional green space, and Eglinton Crosstown LRT access
Ontario's first town planned entirely on paper before a single home was built, Leaside-Bennington became part of Toronto in 1998 and has retained its distinct village identity and prestigious character ever since.
A high-income, highly educated community where 69 percent of adult residents hold a bachelor's degree or higher, families with children make up half of all households, and very low crime rates underpin a strong sense of safety.
Boutique shopping on Bayview Avenue, 147-acre Sunnybrook Park, the Leaside Memorial Community Gardens complex, and a full suite of tennis courts, ice rinks, and ravine trails create an exceptional quality of everyday life.
Leaside was the first town in Ontario designed entirely on paper before any homes were built, planned in 1912 by Frederick Todd, one of Canada's most celebrated landscape architects and town planners.
Leaside-Bennington is among Toronto's most expensive and consistently in-demand residential markets, dominated by large single-family homes with generous lots and strong multi-cycle value retention.
The Eglinton Crosstown LRT is adding underground stations at Bayview Avenue and Laird Drive, giving Leaside-Bennington its first rapid transit connection and direct access to Pearson Airport and Scarborough.
Ontario's first planned town, now one of Toronto's most prestigious and family-oriented east-end addresses.
Leaside-Bennington occupies a distinguished position in Toronto's east end, its identity rooted in a remarkable origin: incorporated as the Town of Leaside in 1913, it was the first town in Ontario designed entirely on paper by a professional town planner before a single home was built. That early commitment to thoughtful planning is still evident in the neighbourhood's wide residential streets, generous lots, and exceptional community infrastructure. Leaside-Bennington homes for sale command significant premiums in Toronto's market, attracting high-income families and professionals, while Leaside-Bennington homes for rent appeal to executives who want the neighbourhood's quality of life with flexibility.
An affluent, family-oriented community with prestigious schools and a genuine village-like character.
Expect a neighbourhood of substantial single-family homes, many built in the mid-twentieth century with spacious yards, mature trees, and architectural character maintained and enhanced over generations. Leaside-Bennington is known for its very low crime rates, deeply engaged residents, and strong community identity. Families with children make up half of all households, and the neighbourhood consistently attracts professionals and executives who value tranquility, top schools, and proximity to Toronto's core.
World-class parks, boutique shopping, and outstanding community recreation facilities within walking distance of home.
Life in Leaside-Bennington centres on an exceptional collection of recreational assets. Sunnybrook Park spans 147 acres with an off-leash dog area, horse stables, and extensive trails. Trace Manes Park provides six tennis courts, a baseball diamond, and an outdoor natural ice rink each winter. The Leaside Memorial Community Gardens houses an indoor arena, swimming pool, curling rink, and auditorium. Serena Gundy Park offers forested ravine trails for walking, cycling, and cross-country skiing, while Bayview Avenue and Eglinton Avenue deliver boutique restaurants, cafes, and specialty shops steps from home.
Unexpected Appeal:
A neighbourhood born from a visionary planner's blueprint, built to last, and still delivering on every promise a century later.
One of Toronto's most consistently prestigious and in-demand residential addresses, with strong multi-cycle value retention.
Leaside-Bennington is among Toronto's most expensive residential markets, where consistent demand from high-income families and professionals has maintained values through multiple cycles. The neighbourhood is dominated by large detached homes on generous lots, with a limited but growing supply of townhomes and condominiums for buyers seeking entry at lower price points. The Eglinton Crosstown LRT stations within the neighbourhood add compelling long-term value to an already elite address.
The village feel, the parks, the schools, and the rare combination of prestige and genuine livability.
You will fall in love with the way Leaside-Bennington manages to feel like a quiet village while sitting squarely within Canada's largest city. Sunnybrook Park delivers nature at a scale that rivals conservation areas, Bayview Avenue offers boutique shopping and dining that neighbouring districts envy, and the schools are among Toronto's most highly regarded. When the Eglinton Crosstown LRT is fully operational, Leaside-Bennington will gain rapid transit connections it has never had, making one of Toronto's finest addresses genuinely unbeatable.
