Hello there,
Here's a map of a town I had been a part of for 13 months on the buxville.net Minecraft server. It changed a lot since its initial creation, I might actually post a post-factum WIP thread too (I have the older versions too).
Note, this was intended to help the mayor govern the town. You see rectangles instead of houses - these are numbered lots. It made more sense to draw these than the actual houses, since lot ownership changed countless times over the months.

Too long a story, here's the map:

Video made by the mayor, so that you can compare the map to the actual town:

Forgot to add: it was made entirely in MS PowerPoint 2007.

I have more of these PowerPoint maps, of other towns on the server (commissions). Might post later :>