Here's an idea...upper end of your price range but most Owners are willing to negotiate. These old Irwins are good sailors and have good draft for the Chesapeake. Not quite as pretty as the CD but, in my opinion, more attractive than the Catalinas or Hunters (not that those are bad boats - just a different aesthetic).
A boat this size would be a good day sailor and also give you a tremendous amount of flexibility in expanding your horizons later if you want to.
(I have no connection to or commerical interest in this boat).
1968 Irwin 31 Sail Boat For Sale - www.yachtworld.com