My 2 cents:
Small communities, especially farming communities, will probably not have many houses sharing walls. But I think it's likely that houses in these kinds of communities will have their own yards, barns, vegetable patches, etc.
Large communities, especially walled cities, will probable have a lot of houses sharing walls. This is cheaper and there is limited space within the walls (or limited space near premium locations, like the market, church, etc).
I do like the handdrawn style by the way Torstan.