Finding a city generator which will produce credible looking cities is a bit like finding the philsopher's stone. There are some automated city generators out there if you're not particular about what your city should look like.
I still remain somewhat convinced that someone who is good at programming could make something with 'Context Free' (google it). I think Redrobes is working on something.
Vector programmes have a brush setting where you can put down 'house shapes' at random following a line, so you can populate a street very quickly that way, (CD3 has a similar option) but the results are a bit 'meh'.
All I can suggest, if you are using photoshop, is to start out with your city as a single solid black shape. Download some references from the web as to what you want your city to look like and start to carve out negative space from the shape using a white brush. It will take ages though.