User blog comment:Thedoucheinthenorth/Should a city-sized Winterhold have been in Skyrim?/@comment-4057437-20121105080352

As was pointed out in the initial blog, there has to be an economic foundation for a city to exist. Aside for the college and one third rate mine, there is nothing in or near Winterhold, not even a shrine to attract pilgrims. The people there are barely surviving as it is.

There IS plenty of empty land, though, as there are no farms or villages nearby.