That’s a tall order and I don’t think you’ll find a filter to do what you want. I think you’re going to have to sit down and find a technique that is reasonably close.
Probably the closest I ever got to that look is:
http://www.artisticphotography.us/St_Johns/ But there’s an incredible amount of touch-up on something like this.
I don’t really remember how I did it but if you want a place to start:
Boost the contrast up to an annoyingly high level and balance the brightness at the same. Going lighter will help you lose detail. Work until you get rid of the detail you don’t want (for example, all of the brick detail). Don’t be afraid of going to 100% contrast and seeing what happens. The image will look pretty wild.
Then start applying filters and see what you get. Start with "find edges". Also try sketch, etc.
By this point, most of the similar types of stuff will be similar colors. Some you will want and some you will not. For example, the road will be some color (and there’s no way of predicting what it will be). Use magic wand to select the colors you want to get ride of and delete them (or change to white)
After you are done, then convert to b&w
Go in and touch it up by hand. Removing things you don’t want.
Then you will probably have to soften it a bit because the lines will be too crisp.
In the end, it will be simpler to have hand-drawn it.
