You can walk in Winterhold without a loading screen, because it doesn't have it's own worldspace like the five major cities do.It does have a large castle from what I've been told though, but the town itself is open.
My impression of Winterhold is the college and a few building that make the town, so i'm thinking it's a few small building and one big one. All of which have there own interior cells like Riverwood (and, well every other building in the game).
I also imagine most NPC's will be inside the college not outside so it's not demanding enough to require it's own worldspace like the cities.