I've always wondered what this tiny, gloomy, haunted looking ruin used to look like before it was almost totally destroyed. Anyone got info or especially pics of what it used to look like before it all went to Oblivion?

i hope we could see it in a future dlc/expansion involving psjiic order,dwever or whatever have been the causes of the great collapse and concomitant volcano eruption in morrowind

I doubt this

But I do hope we get a dlc on par with Hearthfire for us to become Jarl and to build it up a bit. That and have a stone castle home as part of it

I seem to remember that at one point it was the capital of Skyrim, meaning it must have been very large, rich and prosperous at some point, as well as it being deemed a suitable place for a college of magic.

it was the augur of dunlain and his quest for power that brought about the great collapse

i'm ok with the little additions like hearthfire,but i think that a "rebuild dlc" would be more appropriate for helgen,even more because we have only sea and two-three "houses" around the academy at the actual state

however,i think that the opportunity to see winterhold in his former glory would be fantastic for an expansion or a great sized dlc - with a solid plot and concrete choices/consequences of course

ive always wondered this same thing. OP, i dont know what system you play on, but if its PC, theres a very interesting mod related to that on Skyrim Nexus found here:
http://skyrim.nexusmods.com/mods/8333/ i highly recommend it if you're into content mods. its very well done and you can tell the author worked very hard on it. it basically adds ruins to Winterhold and a couple of quests to go along with them.