Craven Rd in Toronto's East End, created from the former backyards of houses on Ashdale. Most of the originals would have been owner built in the early 1900s and probably were close to legitimate shacks before multiple upgrades over the years:
https://goo.gl/maps/ebh8ifUe2LzasNBV7
https://goo.gl/maps/LKYG4LmyDzQsGVYJ8
Toronto's Earlscourt area was more or less a shack town from the late 1800s to around WWI as it was quite hilly (hard to develop), beyond city limits and lacked basic municipal services. Yet was in close proximity to major industry in the West Toronto Junction and Weston and allowed new immigrants to actually purchase land. Dwellings ranged from fairly decent owner built houses to what amounted to a roof over a roughed in basement. The area was no stranger to media at the time and was even featured in Lawrence Harris paintings:
https://www.klinkhoff.ca/blog/7942/
Today the housing stock is fairly eclectic and what appear to be 1940s/50s standard houses can sometimes belay the suprisingly old bones underneath. On a few streets - particularly the hillier ones - some vestiges of what existed remain:
https://goo.gl/maps/NWBQYNAHTJaEFp2r6
The Earlscourt area was perhaps the most well known, but shack towns more or less encircled Toronto at the time, and there was somewhat of a moral panic regarding this:
All of the above from the interesting article here:
https://leslievillehistory.com/the-g...cktown-crisis/
The books "Toronto Sprawls" by Lawrence Solomon and "Unplanned Suburbs" by Richard Harris cover this part of Toronto's history in extreme detail, particularly the latter.