Size of Settlements

I working on creating a bit more detail for the starting town, Threshold, and would like a map. But I don’t know what area it should cover or how many buildings it should have. I’m leaning towards giving it one building for each family, but I’m curious how other people have thought about this.

I use the “1 square mile of land per 38,850 people” average from Medieval Demographics Made Easy to determine how big the urban settlement is going to be. I map urban settlements using a style similar to this 1930’s street map style, where you sketch the borders of city blocks and then highlight landmark buildings.