The village of Montepescini was the domain of the Ardengheschi counts during the early Middle Ages. The bishops and the Capitolo of Siena had the jurisdiction there, as we read in a 1053 diploma of the emperor Henry III and in a note of 1189 of Pope Clement III. It was an important Castle during the thirteenth century. It was so important that a second one was added to the original fortified nucleus of Castel Vecchio, the so-called Castel Nuovo, also called Coppiano, with a parish church. The territory of the people of Coppiano, or Monte Pescini, extended into a portion that also included the nearby hermitage of Montespecchio. When the hermitage was suppressed in 1443 the property of Montepescini belonged to the monks of Montespecchio and than passed to the Augustinian hermitage of Lecceto. Montepescini had 108 inhabitants in 1833. The castle suffered serious damage several times due to Florentine and Pisan raids between 1259 and 1390 which culminated with the war of Siena in 1554 which destroyed the town of Montepescini and turned the entire area to a pile of rubble. In 1601 the Borghesi family bought the ruins of the castle, the remains of the primitive castle were covered by vegetation. To date, the roofs that devastated the interior of the buildings have collapsed, even if the walls are still intact.