55' Bridge height, along with all the other desires/requirments, really restricts you to somewhere north of the Clearwater Causway bridge to Tarpon Springs. There are several paths out to open water from there and still reasonable distance from Oldsmar.
You can usually expect 9' in the ICW but many waterfront homes don't have that kind of water at the dock or access to the dock at anything but high tide. I work for a jet boat/watercraft dealership (don't hate me!) and we have many customers who need high tide to get their jet boats out ....... they draw 12".
The Dunedin area is nice but not much in the way of waterfront you could use, some but not much.
Another alternative is Tierra Verde or Vina Del Mar Island; great Gulf access but a long way from Oldsmar.
Palm Harbor and Crystal Beach would be great but the water is really shallow up there ...............
Good Luck with your search, this is a great place to live.