There are two things people haven't mentioned yet: amalgamations and Interstate highways.
Calgary is a great case study for the first. Calgary actually sprawls pretty aggressively, but it's almost all
in Calgary. The city itself gobbles up surrounding land, services it, and sets the rules for development. If someone wants to develop a parcel of land beyond what the city is ready to service, tough shit.
American cities rarely annex or amalgamate land like this. The administrative patchwork in its stead leads to a development patchwork as multifarious communities allow this or that development.
Further down, you used an example from just outside of Winnipeg. in the '70s, Winnipeg went through a big amalgamation with most of its suburbs. The sprawl you see inside its large city limits is, therefore, orderly and characteristically Canadian. But the piece of land you've asked about is just outside city limits. The rural municipality there probably isn't capable of providing services like sewer and water to a large development. The province of Manitoba has nevertheless put it on the city to extend its water and sewer services to surrounding communities. It's not impossible that this piece of land would develop like you've illustrated, but there's another impediment: road access.
The parcel of land in question has no meaningful transportation connection to the city. In the US, there would probably be a nearby Interstate highway, which would carry drivers directly into the city. There's no such thing in Canada, and cities aren't particularly interested in building roads for residents of neighbouring municipalities to dump traffic onto. There was a recent case on the northern edge of Winnipeg where the neighbouring municipality wanted to permit a Walmart on a street only accessible through the city. It was a shameless property tax grab that would have dumped significant expenses on the city. The city kiboshed the idea by pointing out that they could close the road.
If there was a serious plan to develop the parcel you've asked about, it's likely the city would annex the area.
For what it's worth, there is a fair bit of exurban sprawl around Winnipeg. Directly north of the city looks like this:
https://www.google.com/maps/@49.9726.../data=!3m1!1e3
Very American. The municipalities there want development but are eager to maintain a rural character. It's worth noting, too, that a lot of these Mcmansions don't even have sewer services. I don't know how people who live there can enjoy their pools and huge yards when there's always a shit truck rumbling around, stinking up the place.
A similarly messy situation exists just west of the city.
https://www.google.com/maps/@49.8686.../data=!3m1!1e3
You'll notice that both of these areas have good highway connections to the city.
A lot of exurban sprawl also hides in nearby small towns. The towns are able to provide some services and they sprawl in the orderly Canadian way, just on a small scale. These towns don't have booming local economies; they're just bedroom communities.
https://www.google.com/maps/@49.6063.../data=!3m1!1e3