5 streets with the coolest houses in Toronto

There are cool houses scattered about Toronto, but to snack on a bunch of them at once there are a handful of streets with more than their fair share. Head out on your own architecture tour of Toronto and see some of the incredible contemporary homes that are scattered over the city.

Here’s a roundup of Toronto streets with the coolest houses.

Roxborough Drive

Roxborough Drive would be worth the trip if only to catch a glimpse of Integral House (#194), one of Toronto’s most astonishing examples of residential architecture. A stroll down this street also reveals gems like Barton Myers’ “Wolf House” at #51 and this subtle gem at #177. Naturally there are other historic Rosedale homes along the way.

48 Heathdale Road

Heathdale Road

Cedarvale is chock full of mesmerizing architecture thanks to the presence of the ravine and some very attractive lots, but Heathdale Rd. takes the cake thanks in part to Atom Egoyan’s movie Chloe, which prominently shows off both Ravine House (#24) and Heathdale House (#48) – the former was used for interiors and the latter for exteriors. 

83 Bridle Path

The Bridle Path

Virtually every house on this street and in this area is stunning (or shocking). The downside is these properties are often set far back from the road and hard to see. One of my favourites is at #83, but the neighbourhood standout is 18 High Point Rd. Drake’s new pad can be easily ogled from the street at 21 Park Lane Circle.

Draper Street Toronto

Draper Street

You won’t find any modern houses on Draper Street, but this little thoroughfare that runs adjacent to Portland St. up from Front St. is like a time warp back to the 1880s in Toronto. These row houses were originally built for labourers, but now house residents with a fierce commitment to retain the historical character of the street.

Wychwood Park

Wychwood Park

Wychwood Park is fascinating for a whole bunch of reasons, not the least of which being that it’s a gated community. The houses here are worth a visit too. Some of the best examples of Arts & Crafts architecture in Toronto can be found here, but also contemporary highlights like Ian MacDonald’s residence at 4a.

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