The earliest Annunciation icon

The oldest surviving icon of the Annunciation is found in the Catacomb of Priscilla on the Via Salaria in Rome, Italy, and dates from the second half of the second century A.D. Priscilla is thought to have been a well-to-do Roman who converted to Christianity and was martyred. More information on this icon and its development over time at the wonderful blog, A Reader's Guide to Orthodox Icons.