Neat. This is Forest Hill Village — which is just a bit north of Spadina & St. Clair — in 1927. It was brand new back then: the village was incorporated just a few years earlier and wouldn't be officially swallowed up by the City of Toronto until 40 years after this photo was taken.
Just a block to the west (i.e. to the left) of this spot is Cedarvale Ravine. Hemingway lived not far away just a few years earlier than this, and he'd take walks along Castle Frank Brook, which runs along the bottom of the ravine. It's also where the city planned to put the Spadina Expressway in the 1960s, until the famous grassroots campaign forced them to cancel the plans.
We're looking north at the intersection of Spadina & Lonsdale. That building on the north-east corner is home to a Second Cup now. The one of the south-east is a restaurant with yoga upstairs (Um, well, last I checked, anyway — it's just a few minutes from my place, but I don't go over there as much since my favourite breakfast place closed).