Despite its remodelling in the course of the 18th century on the occasion of its transformation into a villa, the Meleto Castle still betrays its military vocation in its irregular four-sided plan with the keep tower in the middle. Originally (11th century) in the possession of the Vallombrosan monks of the nearby Abbey di Coltibuono, the castle was at length contended by the provinces of Siena and Florence, for its position of control over the road connecting the Upper Valdarno and the Chianti territory. It remained at length a stronghold of the Florentines who, in 1480, reinforced its defensive structures. In particular, two powerful cylindrical keeps built at that time, present the typical characteristics of contemporary military constructions: a high scarp, a vertical segment marked by projecting double cordons in stone, the defensive system projecting on triangular stone corbels and little brick arches, and the insertion of embrasures for both archery and cannons, today in part lost. Never destroyed, but partially dismantled to transform it into a villa in the first half of the 18th century, it still conserves the furnishings of the period, including a little theatre of 1742 equipped with seven original sceneries. Property of the Ricasoli family until 1968, it is today the headquarters of a prestigious winegrowing firm.