Anavatos’ first settlers were lumberjacks, to whom the emperor Konstantinos Monomahos assigned the construction of Nea Moni. Lumberjacks were so impressed by the beauty of the landscape that they asked the emperor to grant them the ground. The emperor accepted that, as he was very satisfied from their conscientious work. The lumberjacks planted olives, cultivated vines and created beehives.   
Nonetheless the days of prosperity did not last long, as the village was attacked repeatedly from pirates. The pirates arrived at the beach of Elinta and then went up to the village. The village was burnt many times from the pirates, until it was completely   destroyed.
Then on that steep rock the second settlement began, by those who had been rescued: 400 houses, school, church, courts and prisons were constructed, all of exquisite architecture. The placement of Stone in the houses with arches, the arcs, the small and narrow streets, gave in the village an intense medieval character that still emerges from the ruins that begin to fall apart. 
During the Medieval period, people from Anavatos were attacked once more from pirates. The descriptions of foreigner sightseers are the older reports that still exist and inform us about the life of this unique village in the Aegean. The French historical Jean Dumont, that passed in 1690 from Anavatos, reports: "The residents, which are few and very poor claim that as tradition says, Omiros was born there and cultivated a vine that belonged to him, the famous Omiros’ vine. Almost the same reports about Omiros are written by the eminent Venetian geographer Vincenzo Maria Coronelli in 1696 who adds, "the vine produces the most delicate wine". He also mentions that "the number of residents is 150 only". Another sightseer that passed in 1656 from Anavatos, the French Jean Thevenot, certifies the above, adding the production of coal.