At its Southern tip, I exited onto the Heath St. entrance of the St. Clair station. Lower Village Gate was a gated community comprising of 2 low-rise condo buildings facing a row of townhouses, all fenced off from the surrounding streets. Pedestrian walkways gave access to it during the day. At the Eastern end, the ravine merged into Suydam Park and Forest Hill (South).
At first, this neighbourhood didn't live up to its chi-chi reputation. But further exploration of streets like Dunloe, Hawarden, Vesta, Burton, and Delavan revealed enormous homes where the second car was a Mercedes or BMW. Afterwards, I looked at satellite images and saw that they hid large backyards complete with swimming pools and even small basketball courts. The architecture was eclectic but none of it felt old. I suspect Forest Hill's new money reputation played a role; it was as if the suburban enclave of Oakville was dropped into Toronto. There was almost no one around except for tradespeople fixing roofs, paving driveways, or landscaping front yards.
Finally, around Spadina and Lonsdale, I found pedestrians amid a cluster of old buildings housing apartments and shops. They barely covered a city block and didn't stand out: bank branches, Subway, Starbucks. Perhaps the residents of upscale Forest Hill mostly drive elsewhere for restaurants and other amenities.