I'm trying to remember the most housing crowded airport I flew into as
PIC.

Midway comes to mind. LGA is pretty crowded, so is what used to be
called Washington National.

For general aviation, Lakeway in Austin is in the middle of a housing
development. Some houses near the airport have hangers, not garages.
Gee, the remote control for a garage door is still another radio in the
airplane.