Montecchio Vesponi is a small village part of the municipality of Castiglion Fiorentino, province of Arezzo. Located 4 km south of Castiglion Fiorentino, it lies on a hill at the bottom of the Chio valley, 364 m above sea level. There are about 1200 inhabitants.
The first dwellings on the hill of Montecchio date to the Etruscan and Roman periods when a sanctuary might have been built there. Around the 9th century the castle was built, part of the fee of the Marchiones family and related to Farneta abbey. Other related feudal were the Orselli and Panzoni of Cortona or the Da Vitiano.At the beginning of the 13th century, it became allied with the municipality of Arezzo and the castles of Mammi and Monticello.In around 1234 it was bought by the municipality of Arezzo which settled more people there, making it a municipality under its influence and a stronghold against Castiglion Fiorentino and Cortona.
In 1281 Arezzo enlarged the castle walls completing the fortress which is visible today, making it similar to Montecolognola and Monteriggioni, and settled families in the interior.In 1289 after the defeat suffered by Arezzo in the battle of Campaldino it passed to Florence. It switched back to Arezzo in 1303 and at the beginning of the 14th century was a stronghold against Perugia.
In around 1383, the Arezzo military being weak and without control of its territory, the castle was occupied by John Hawkwood, known in Italy as "Giovanni Acuto", who settled there. Upon his death (1394) Montecchio became again the property of the municipality of Florence and was used by Florentine administrators.
It was made part of the Castiglion Fiorentino municipality in 1774 with administrative reform of Leopold II, Duke of Tuscany.
In the 19th century the castle, formerly subdivided into many small properties, was bought by a Servadio banker who started restoration work. It was later sold to the Budini-Gattai family which restored the tower and continued consolidating the walls. It was then abandoned. It became the property of Countess Orietta Floridi.