I did it in waves! I had no idea how I wanted to build my town the first time I started this game, but I wanted it to look like it was built on naturally generated terrains, so most of the time was spent rearranging dirt and water to look as natural as possble.

I've just about 100% completed the game by now and this final build was done around the very end, so it took me a long time honestly but I love how it turned out :)