A small ravine-bounded pocket south of Leaside, quiet and tightly held.
Written by Nick Ntoukas, Toronto realtor · Chestnut Park Real Estate · Updated August 2026
Bennington Heights is a compact neighbourhood south of Leaside, cut off from through traffic by ravine on three sides and reached by a small number of streets. That isolation is the point: it is genuinely quiet, the ravine trails are at the door, and the housing is a mix of interwar and postwar detached homes on good lots, many since expanded or rebuilt. It shares Leaside’s schools and much of its family character while feeling considerably more secluded. Very little comes up for sale in any given year.
Detached houses, interwar and postwar, many substantially renovated.
Families, often moving from Leaside for more space and quiet; long-term owners.
The Bayview bus south to the Bloor line; the Eglinton Crosstown to the north.
Access is limited to a few streets, which matters in winter. Drive the routes before deciding.
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Straight-line distances from the centre of Bennington Heights. Proximity is not catchment — check the board locators or ask Nick. School locations: Statistics Canada, Open Database of Educational Facilities, adapted; contains information licensed under the Open Government Licence — Canada.
Worth a look if you like Bennington Heights — each has its own guide, live listings and schools.
Nick Ntoukas is a Toronto real estate agent with Chestnut Park Real Estate Limited, Brokerage — the exclusive Ontario affiliate of Christie’s International Real Estate — working with buyers and sellers across the GTA, including Bennington Heights. A written valuation of your Bennington Heights home is free and arrives within 48 hours: call 647-208-8588 or request it online.