Had to keep coming back to look to find the things my mind was saying "something just seems...off".

It is good, great even, but I do agree with some of the comments above. The fields & trees and stuff seem to have a slight bluring effect on them that does not exist on the buildings. As to the shadows...the seem almost all uniform. When I do cities like that in CC3 I try and put the trees on one sheet, the hedges on another, the walls & towers on a third, and the buildings on a forth. I then apply different length shadows to them to give the illusion of different heights. You also maybe might want to 'harden' the shadow effect a bit so they show up more.