The town of Monteleone, which arose spontaneously around the castle, saw its development in the epoch of the lords: the exact origins are not documented, although we know that around the year 1000, the castle was owned by the church of Ravenna, in struggle with Rimini for the property.
Just in the fourteenth century Rimini built a first real fortress, held by the Malatesta family until 1335, then lost to Francesco degli Ordelaffi di Forlì then to the Montefeltro, to return under the control of the Holy See and subsequently, in 1433, again to the Malatesta .
In 1485 it returned under the control of the Archbishop of Ravenna, and was given to the Roverella di Cesena who held it until 1745, making extensions and the transformation from a castle into a summer residence. At the same time, the construction of houses on the ancient wall circuit was encouraged, demolishing the previous ones more leaning against the building and creating a hanging garden in their place.
In 1960 the castle was sold to the current owners, the Volpe counts (currently the castle cannot be visited).