The Central Square, of Renaissance imprint, embellished by "Logge del Vasari" (XVI century). Decorated with coats of arms in stone and clay and an ancient fresco. Facing the Logge the "Palazzo Comunale" of 1500, then rebuilt in 1935.

The Municipal Gallery (Pinacoteca Comunale), housed since 1991 in Cassero (XI-XII century),is a rich collection of works from local churches. The building includes the Church of St. Angelo, including the museum, where, in addition to paintings from the thirteenth century to the fifteenth are three masterpieces of medieval goldsmiths.

The "Pieve a Rétina", built in the XII-XIII century, has Renaissance forms and the interior has three naves.

The Castle di Montecchio Vesponi, situated on the road that connects Castiglion Fiorentino to Cortona, was donated by Florence to the captain Giovanni Acuto after the battle of Campaldino.