The first documents referencing the Casamassella Castle and the settlement which surrounds it date from medieval times, when the castle was the fortified residence of the fiefdom of Ruggero Maramonte under the reign of Carlo I d’Angiò (Charles of Anjou).
Its geographical location in the hinterlands immediately bordering Otranto, hidden from the frequent incursion by barbaric pirates, Turks and Algerians along the coast, made the Casamassella Castle a secure and prestigious residence, coveted by some of the most noble families of the land of Otranto. As the years passed, different owners came and went and the Castle experienced many changes, but still remained at the centre of the agricultural village of Casamassella. The large, deep moat which surrounded it disappeared, along with the drawbridge; new windows and entrances were opened. In 1700 its function changed completely and the fortress, once characterized by severe military architecture, became an elegant noble palace. In those years the castle belonged to the marquises de Marco. In 1800 the de Marco family adopted the De Viti brothers, one of whom, Raffaele, would become the father of the famous economist Antonio De Viti de Marco (1858-1943), defender of the economic interests of Southern Italy and author of numerous works of international renown. Many important guests frequented the reception rooms of the Castle, including Benedetto Croce. The De Viti de Marco family lived in the Castle until 1969, when it passed to the present owners.