It is an old cape cod style, and the paint job now has a lot of texture from what looks to be many years of paint jobs.
I recal seeing an episode with Bob Vila where they repainted and old place in Florida (I think) and they seemed to be dealing with the same issue. To get a smooth finish they had to either scrape 100% of the paint off or use some sort of filler. I am not sure but I seem to recall them using a filler which they later sanded down for a nice smooth appearance before priming and painting.
Can anyone recall this episode or have any experience dealing with this problem.