As part of research in the broader Anopoli region, at elevations of 600 to 800 meters, a few sites dating to the Late Neolithic / Early Minoan period have been discovered. The remains of ancient Anopolis (as referred to by Stephanus of Byzantium) are located on the hill of Agia Ekaterini, west and southwest of the modern village of the same name. Its position provided extensive control over large areas of land as well as the Libyan Sea. Maritime communication, as an intermediate station between East and West, was ensured by the port of Phoenix, modern-day Loutro. Ancient sources report that in the 3rd century BC it was occupied by neighboring Aradena and later liberated by Charmadas, a citizen of Anopolis. This period likely corresponds to the first phase of its fortification walls. Between 230–210 BC it is mentioned in a list of cities that sent theoroi to Delphi. Anopolis, along with Aradena and Poikilasos, is also recorded among the cities that signed a treaty with Eumenes II of Pergamon in 183 BC.