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The first reliable news of the existence of the castle of Caldarola dates back to 1191 when Celestino III, granting papal protection to the abbey of S. Clemente di Casauria in Abruzzo, allowed the monastery to enjoy its possessions in the Marche and among these there was also the castrum Caldarole. The castle, most likely built in the 10th century to protect the Benedictine court, must have consisted of a simple wall with a watchtower. The current Cassero tower most likely rises on the foundations of this ancient tower.
The castle restorations carried out in 1460 must not have affected the tower because in a painting by the painter Lorenzo D'Alessandro depicting the Madonna della Misericordia and made in 1491 there is a view of the castle of Caldarola dominated by an austere square tower mutilated by the battlements and ruined part facing outwards. Most likely at the time it had already been abandoned because it no longer responds to the new defense techniques.
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