At the highest point of the place between the eleventh and twelfth centuries the fortress and castle were born, the first a rectangular fortification with the smaller rounded sides and, beside it, the primitive village from which the “castle” originatedIt is also surrounded by walls and with a more complex urban texture.
...The fortress is the first medieval defensive nucleus of Castelleone built around the XI-XII century on the edge of a cliff that characterizes the peak of the hill overlooking the river Cesano. The fortification has a rectangular shape with rounded sides and next to it there is the primitive village from which the “castle”, also surrounded by walls and with a more complex urban texture. Fortress and castle had to adapt to the morphological conformation of the place and the dominant lines of the only road connecting with the Benedictine Abbey of San Lorenzo in Campo where the territory belonged. Right under the fortress and in front of the primitive village, on 5 March 1266 Cantagallo di Cagli and Giovanni di Giglio, captains of men and of the University of Castelleone, together with the parliament of the 57 men of the castle, designate Accorimbona di Egidio as their mayor and prosecutor for submission to the Municipality of Rocca Contrada (now Arcevia). In that period the place is Rinaldo di Brunforte who is also present in the powerful mountain town, of which he became rector in 1288. A little more than a century later, and precisely on November 26, 1371, the same place is the scene of another important event for the suasana historiography. The abbot Reginaldo presented himself with the bull of Gregory XI of 31 August of that same 1371 to ask for the restitution of the fief stolen from the Abbey fifteen years earlier by Cardinal Egidio Albornoz and finished in the Apostolic Chamber.At that time, in fact, the Abbey had a dispute with his wife and the daughter of Ottaviano last of Brunforte lords of Castelleone who claimed the reinvestment on the fief. In the process of reorganization of the Marca, the Legato in Italy had seized the ball and confiscated the territory then infeudato the Florentine Bindaccio Ricasoli. That now, after three favorable judgments to the Abbey laurentina, can not do anything but return the fortress, the castle and its curia with all rights, jurisdictions and relevance. The direct possession of the Laurentina Abbey, however, lasted only fifteen years, because then the contested Abbot Nallo of Civitanova in 1386 granted the fief of Castelleone to Niccolò Castracani of Lucca, his wife Onofria and his mother-in-law Catherine. The two women, however, are none other than the daughter and wife of Octavian last of Brunforte lords of Castelleone. And precisely against the Castracani the new abbot Ugo di Montevecchio will have to make formal protests for the concessions made to the massari, men and the University of Castellone on the occasion of the fortification of the castle.The notification this time takes place on the square of the fortress at the primitive church of San Pietro. To present it on 22 May 1457 is Giovanni di Antonio di Fossombrone, parish priest of Montalfoglio and spiritual vicar of the abbot. Under penalty of excommunication the new lords of Castelleone must thus recognize the full ownership of the monastery on the houses, ditches, banks and appliances, of which they must request the renewal. With the passage of time the defensive needs are attenuated and the fortress gradually loses its pre-eminence to the advantage of the castle below that especially with the Della Rovere develops. In front of the fortress there is a new village outside the castle walls and along the predominance line determined by the road connecting with San Lorenzo in Campo. This will be followed, starting from the seventeenth century, by a new development along the road to the convent of the friars Minims of San Francesco di Paola, wanted by the brothers Giuliano and Ippolito Della Rovere.