The village of Monteleone grew organically around the castle in the era of the great noble families. Its exact origins are uncertain, although we do know that around the year 1000, the castle was owned by the church of Ravenna, which was vying for supremacy with Rimini.
The Malatesta family of Rimini built a proper castle in the 14th century; Francesco degli Ordelaffi, Lord of Forlì, took it off them in 1335 before losing it to the Duke of Montefeltro, only for it to come back under the church’s control and boomerang back to the Malatesta in 1433.
The merry-go-round resumed in 1485, when it returned to the control of the archbishop of Ravenna before then being taken over by the Roverella family of Cesena. They held it until 1745, extending the castle and turning it into a summer residence, while encouraging house building around the old walls, demolishing the existing dwellings by the main house and establishing the hanging garden.
The castle was sold to its current owners, the Counts of Volpe, in 1960 (currently the castle is not open to the public).