The geographical position in which it rose, in the immediate Otranto hinterland, 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, who in the course of the centuries occupied it. It belonged to the Sambiasi, to the da Noha, and then the dell’Antoglietta until 20 May 1476, when King Ferrante d’Aragona, reconfirmed it to Filippo Antonio Maramonte (descendent of the first feudatory) as a reward for all his military successes. In those years, the events regarding the Kingdom of Naples, were in fact characterised by the rebellion of the Barons, and wars with other Italian States. Through the centuries the Castle changed feudatory again.

In the 1500 it belonged to the Paladini and then to the Rondachi, a family of Greek origin, who resided in Otranto. They owned much of the land in Salento.

According to studies by Florio Santini (a contemporary and renowned writer, who was conquered by the charm of Casamassella) in 1600 the Castle was inhabited by Spanish governors, among whom was Michele Fernandez da Azedo, this was followed, after a short return of the Rondachi, by Didaco Perez Serrano, and by the “Vicario Generale” Don Giuseppe Centonze. As the years went by, and different owners came and went, the Castle underwent many changes, but it remained the centre of the agricultural village of Casamassella.

The large and deep torrent which surrounded it disappeared, as did the drawbridge; new windows and entrances were installed. In 1700 its functions changed completely and the construction was fortified, however out of the severe military architecture, emerged an elegant and noble palace, the façade was refined by a windowed balcony over the main entrance. In those days, the castle belonged to the Marquises de Marco. In 1800 the de Marco adopted the De Viti brothers, one of the two, Raffaele, father of the famous economist Antonio De Viti de Marco (1858-1943), defender of the economic interests of the “Mezzogiorno”, and author of many works which have international fame. Oak trees in the courtyard of the Castle are dedicated to Lady Caroline and Lady Giulia, mother and sister of the Economist. Both women, very well educated contributed to spreading of the art of “the fiocco” of Casamassella.

Over the years, many important guests have frequented the reception rooms of the Castle. We can recall Benedetto Croce, whose wife was a close friend of Lady Caroline. In 1890, the poet and essayist, Girolamo Comi, Baron of Lucugnano, was born in the Castle. An artist with a complicated and original personality, who according to the critic Caporossi, gained him the appellative of “ascetic narcissus”.

The De Viti de Marco family lived in the Castle until 1968, when it then passed on to the present owners, the De Donno family.