This outpost was built to serve as the base for a bandit gang that was posing as carpet merchants, and was part of a 3-year campaign using the Worlds Without Number fantasy tabletop roleplaying game. See below for more info & a close-up detail image.
I run games in a very sandbox style, where there are no predetermined outcomes or right answers, so it was up to my players to decide on their approach to this location. They were aware that there were bandits in the area, but not their precise location. As such, they approached this outpost with caution, but not open hostility. They were welcomed in, offered tea, poisoned by said tea, and then thrown into a battle whilst dealing with the resulting sickness.
At 50x50 grid squares (representing 250 by 250 feet), it's a fairly large map, primarily because I wasn't sure whether the characters would give themselves away before even getting inside. Such a ranged battle would likely have turned out very differently, as there were lookouts with crossbows on the roofs. Similarly, I needed players to be able to see the stilts holding up these buildings, in case they wanted to hide there (they did end up disintegrating part of a building floor, so it was a contingency that paid off).
The final map was set up in Foundry VTT, my personal favorite option for running tabletop RPGs virtually.
This map was created using Dungeondraft and primarily using assets by Forgotten Adventures, although a sprinkling of assets by Tom Cartos were utilized as well. Created for personal use only.
Detailed view of the outpost's interior.