Collesano Castle was built during norman domination at the behest of Countess Adelaisa around 1100, when King Roger destroyed the castle on Monte d'Oro (Qal-at as-sirat = Rocca della Strada) because of the disputes with his brother in law Rainuph. The first document mentioning the castle comes from 1194: this document states the castle donation from king William III to the Archbishop Bartolomeo from Palermo.

The same document also proves the break-up of the Norman dynasty. From the 13th century the castle passed to Cicala family from Alife. With Anjou domination the castle passed to De Monfort family and then to Giovanni De Bullasio. With the birth of the new Collesano county, after the War of the Sicilian Vespers, the castle and its lands were held by Francesco and Antonio Ventimiglia for most of '300. Later, during '400, after Antonio Centelles, all the county passed to Cadorna family and then to Moncada family until '600, when the castle reached the pinnacle of its architectural value and one of its widest hall was transformed in a theatre for representations, religious mostly, presented by the local Accademia degli Offuscati. The 1693 earthquake made the castle unusable and was no longer restored due to noble families decline and indebtedness. Only the "Sacra Famiglia" painting from 1688, author unknown, shows an image of the castle still intact and Collesano urban and architecture layout at the end '600. The painting, once preserved in Chiesa del Collegio, has been recently moved to the Basilica di San Pietro. Lately, the castle was held by Ferrandina dukes during the '700 and by Alvarez from Toledo during '800. Nowadays the castle is still unusable, and only its ruins can be seen.