On the hill above the Annex: substantial houses, steep streets and long views.
Written by Nick Ntoukas, Toronto realtor · Chestnut Park Real Estate · Updated August 2026
The Casa Loma neighbourhood takes its name from the castle at its centre and occupies the escarpment above the Annex — which means genuinely steep streets and, from the right houses, views south across the city. The housing is substantial and varied: large Edwardian and interwar detached homes, some grand, alongside semis and a stock of converted apartments closer to Dupont. It is a short walk to the Annex and to St Clair, and the topography keeps through traffic down. Buyers are often drawn by the combination of scale and proximity to downtown, which is unusual at this price point.
Large detached and semi-detached houses, apartment conversions near Dupont.
Families, professionals, and buyers who want scale within walking distance of the Annex.
Dupont and St Clair West stations; the Bathurst and Spadina bus routes.
Hillside lots can carry drainage and foundation issues. A thorough inspection matters more here than most places.
Loading listings…
Straight-line distances from the centre of Casa Loma. 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 Casa Loma — 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 Casa Loma. A written valuation of your Casa Loma home is free and arrives within 48 hours: call 647-208-8588 or request it online.