A changing neighbourhood of modest houses with a strong Caribbean and Italian history.
Written by Nick Ntoukas, Toronto realtor · Chestnut Park Real Estate · Updated August 2026
Oakwood Village runs north and west of St Clair and Oakwood, and it has one of the more distinctive cultural histories in the city — a long-established Italian community, later joined by a substantial Caribbean one, both still visible in the retail along Eglinton and St Clair. The housing is modest by midtown standards: mostly semi-detached and detached brick on narrow lots, much of it unrenovated until relatively recently. That has made it one of the last genuinely accessible entry points into midtown, and renovation activity has picked up considerably. The Eglinton Crosstown runs along its northern edge.
Semi-detached and detached brick houses on narrow lots; some duplex and triplex stock.
First-time buyers, young families, and long-established local owners.
The Eglinton Crosstown; the 512 St Clair streetcar and the Oakwood bus.
Many houses here are legally duplexed. Confirm the use and any retrofit requirements before you buy.
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Straight-line distances from the centre of Oakwood Village. 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 Oakwood Village — 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 Oakwood Village. A written valuation of your Oakwood Village home is free and arrives within 48 hours: call 647-208-8588 or request it online.