Many sixteenth and eighteenth century sources reference “San Caloiro” as the region of the Pantacus River, named by Ptolemy (second century BC), Virgil (first century BC), and Ovid (first century BC).

In 1768, Nicolas Lenglet Du Fresnoy - scholar, philosopher, and bibliographer of alchemy - explained in his book “Méthode pour étudier la géographie,” that Sicily was among a list of Greek colonies referenced after contemporary locations. The town of San Caloiro is associated with the Greek colony of Trotylum. Inside our estate lies tombs from the ninth and tenth centuries BC, as well as a cave which served as a place of worship in the Byzantine era. It is said that the presence of a saint on these lands influenced the name that first appeared on the documents when Riccardo Passeneto, a nobleman from Normandy, founded the “Encomienda” under the knightly order of Saint James of the Sword. There also once stood a castle, unfortunately now destroyed, on the estate that was carefully depicted by Camilliani in the sixteenth century. The encomienda was later granted to the Gaetani family (Princes of Cassaro and Marquises of Sortino, ancestors of maternal lineage of the Matarazzo’s - the current owners of the estate). After a disastrous earthquake in 1693, the Masseria was almost entirely rebuilt on the ruins of the fourteenth century abbey. At the beginning of the nineteenth century it was already beginning to deteriorate, and was rebuilt in the east wing of the main house and the remainder of the buildings, including the chapel, maintained their original function. Outer buildings were subsequently constructed to give the manor its current small country, village-like appearance.

Over the last two centuries, the house has been inhabited more frequently by its owners, the aristocratic family, not only for the administrative needs of the estate, but also because the house became a cherished retreat for many members of the family who spent most of their time hunting, horseback riding, and gardening. The estate remained a hunting reserve until the 1970’s and is still home to the family’s farm of horses, one of the oldest existing in Sicily. The Commenda di San Calogero is a Grade I listed building in history for its architecture and presence of archaeological remains. It is also a member of the Association of Italian Historic Houses (A.D.S.I).