If we had any kind of clue as to what you are looking for, we might be able to steer you to and away from areas, but since we don't know if you are looking for a 20' daysailer or a 60' ocean crosser, we can't help.
Are you afraid that if you told us what you were looking for, we would all run out and buy up all the available inventory and leave you high and dry?
I'm only guessing here (since that is all we are allowed to do) but my guess is you are looking for something cheap that will most likely only be found walking the docks and boat yards. All the better (and more expensive) boats will be found on the major web sites like Yachtworld. Whole lot easier searching the web than driving all over the country.
I could tell you lots of places to look around the Chesapeake Bay but if you are looking for something larger, say 45 plus, you would be wasting your time going to most of them.
If you gave us some idea of what you are looking for, there's a good possibility someone here on SN knows of a boat that would suit your needs perfectly.