It's certainly true that there are certain buildings that almost always have clear space around them. Churches are the obvious case. Markets are anothe good example. Then municipal buildings come in. Other than that I am certainly struggling to think of any reason for there to be clear space between buildings. I guess the issue of keeping everyone inside the city walls forces buildings to crowd up too.
Good thing I asked here before embarking upon a large settlement!
Certain factions might have the clout to sort of 'own' land too - greens, gardens, stables & space for security might exist for the very powerful. The balancing factors would be of course that most often no one but the city rulership had real control of the land and every cottage or family probably paid taxes.
If you were a knight with a manor in the city you might have grazing rights or clout enough to stop hangers on from building off your home. Your use of the land might deter builders.
If you had no prestige its unlikely you'd get much support because the new building probably meant more taxes in one manner or other. Green space would be at the whims of the city and likely trampled and plundered unless you had a wall around it or something.
I like your hand drawn look. How hand drawn is it?
I'll quickly echo the other comments about urban planning/spacing.
Otherwise, the style is great! My one nitpick is that the building shadows look less "hand drawn" than the rest of it. But that's not really a criticism, just an observation.
It's all hand drawn, though the building outlines are all from the same 9 outlines just rotated and flipped - but they were hand drawn initially. No filters used other than to create the underlying background texture.
Good ideas guys. I'll factor them into version 2.
My thought is that a town would have spaced buildings where a city would have the common wall thing. I think people pay far too much attention to that and think that every settlement has to have joined condominium type housing. Personally, I hate the common wall...reminds me of having to listen to my neighbor's tv when I lived in an apartment, or listen to people argue in the hotel room next to mine. By the way, I like your town style.
The drawing style is wonderful.