Winnipeg skyline ca. 1920.
The taller buildings in the background basically line Portage Avenue from Portage and Main on the right to the Eaton's store on the left.
The homes and smaller buildings in the foreground were almost entirely demolished in the years following WWII as downtown gravitated south from the City Hall/Old Market Square area towards Broadway and the Legislature. Many would agree that this was a catastrophic planning mistake as the end result was spreading downtown Winnipeg over way too large of an area.
Source:
City of Winnipeg Archives