Tips on Making a Town Map less Photoshoppy

[Midgardsormr]

For the shadows: Make a copy of your buildings, fill it with your shadow color (try a dark grey-blue, very low saturation), then give that layer a bit of a directional blur. Offset the layer such that shadows only stick out in one direction. That will solve the floating block problem. Give it a small Gaussian blur to soften the edges, probably.

More generally, I can see that one issue you have here is that everything looks a little plastic. Thatch and wood shingles don't really reflect all that much specular light. Try reducing the opacity of the highlights and shadows so that your shading is a bit subtler. Look at the shading on your hills to give you an idea of the level of light you want to see on the roofs. The shadows will be a bit deeper due to the steepness of the roofs, but the highlights should not be any stronger than what you see on the grass. From the looks of things, you might want to simply turn the higlights off entirely and let the bevel be carried entirely by the shadow.

Ultimately, the only way to make something look less filtered is to paint it by hand. Yeah, that means that towns are a heck of a lot of work! There are procedural solutions to some things, but nobody's found a silver bullet yet. You might take a look around the forums for Ravells' work. He's been looking into city generation techniques harder than anyone else I'm aware of.

[EricPoehlsen]

Give it a small Gaussian blur to soften the edges, probably.

Don't overdo on shadow blurring, real sunlight makes pretty crispy shadows...