The old core of Montesperello’s castle was built in 608 by Bernardo Montesperelli. In 997 Ottone III gave it to the abbey of Campoleone, the current Capolona near Arezzo, for will of  Ugo, abbot and marquis of Toscana, son of the countess Wilma. Ugo, even if he was an abbot, he married  Giuditta, niece of the emperor, because, at that time, it was allowed the marriage in order to secularize the ecclesiastical fief.  Montesperello belonged to the countryside of  “Porta Santa Susanna” and in the list of 1282 was cited like villa with 30 inhabitants.  In 1361 took shelter there Averardo II Montesperelli with his followers. He was captain of the Perugia’s noblemen, and in 1343 he went to Firenze like ambassador of Perugia with Orlandum d. Nini jurperitum e Cecchum d. Peronis de Micheloctis.  The castle was attacked and razed to the ground in 1380.
From that moment, until 1438, it will be called again with the term villa. In 1402 the papal troops sacked and devastated  the place that was considerated very important for its position.  But Perugia reconquered it soon.
Meanwhile the Montesperelli had took shelter in Perugia, in the parish of Santa Lucia. The 20th August of 1433 the brothers Averardo III, Nereo, Periteo and Giulio di Guidone di Paolo de nobilibus Monte  were booked for 1.097 pounds.
In 1439 the castle was rebuilt because Perugia considered it a strategic place, although there were no more than 15 inhabitants. In 1456 was called loctus  and it’s possibile to deduce that the defensive works were not finished.  
 Roberto Malatesta and his garrison encamped there in June 1479. Malatesta (1440-82),called the Magnifico, was the illegitimate son of Sigismondo Pandolfo (1417-68). The latter was  lord of Rimini and lieutenant general of the papal troops. They stayed there only few days because the 28th of June the troops of Firenze, after the conquest  of 23 castles on the Trasimeno Lake, attacked Montesperello and completely defeated the papal troops.
The castle was considerably  damaged during this last battle, but in 1495 it was rebuilt by  Averardo IV in accordance with  particular defensive plan in order to give it again its dignity and its function of a castle; in 1501 there were already 50 residents. In 1496, Averardo IV became magistrate of Fabriano. The castle was for centuries a fief of  Montesperelli’s family, to whom belonged jurisconsults, men of letters, wises of the “Collegio del Cambio”, priors, mayors and judges.
Giovanni I, mayor of  Pisa, built the fortress of Torricella, near Magione;

Ceccolo di Averardo I died in Montecatini in 1315; Neri, conspired in 1385 to consign Perugia to Barnabò Visconti: in the summer 1368 the conspiracy was found out and the popular Government sent him to the scaffold; Averardo V, poet and writer; Zopiro, politician.
In the nineteenth centuries Montesperello belonged to Luigi Massini (1820-96), one of the wealthier men of  Trasimeno Lake; then it belonged to Giovanni Battista Piceller, a notary, father-in-law of Aurelio Angeletti (1832-67), mayor of Magione, who had married Piceller’s daughter  Prassede. When Aurelio died, Prassede was one of the richest landowner of the place. To the Angeletti followed  Renzoni first, director of the fair of Milan, and then the Bartoccioni of Magione.
The present residential villa  is very different from the old building, that during the centuries has been an hospital for poor people, too. A steep way down, outside the villa, flanked by remains of a roman villa, leads to the San Cristoforo’s church.
The Pesciarelli’s family from Magione is the present owner of the castle.