The name of the Castle of Montecchio Vesponi derives from a corruption of “Castrum Montis Guisponi”, a name acquired from the last name of the Aretine family that originally owned the locality. This small fortress, built on a “monticulus” at an altitude of 364 metres a.s.l., has been documented ever since the 11th century, when it seems to have originated as a sighting point. The approximately thirthy-metre-high tower became gradually surrounded by the crenellated walls that can be dated well into 13th century.

The characteristic of its military function over the underwent Florentine domination, during which it was awarded for about 10 years (1383-94) to the soldier of fortune John Hawkwood (who, in Italian, became Giovanni Acuto), thanks to the services which he had rendered to the “City of the Lily”. During the entire 16th century, the Medici were successful in reclaiming a good part of the lands in the plain below the castle. These went to constitute the extension of the estate of Montecchio, the largest of the eight enormous agricultural entities which in the following century were to give substance to the properties of the reigning house, administered by a special body: the Office for Court Possessions. In 1641, Grand Duke Ferdinando II de’ Medici granted the castle in fee for six years to Marchese Tommaso Capponi, after which the small Commune remained on its feet until 1774, the year in which Grand Duke Pietro Leopoldo of Lorraine annexed it to the Commune of Castiglion Fiorentino.

Notwithstanding the concomitance of these identities, between 1651 and 1685 four of the eight Medici estates were made over to the Sacred Military Order of the Knights of Santo Stefano, of which the Medicis by right were always to cover the role of Great Master. The estate of Montecchio was then sold in 1685 to the Order (or Religion) of Santo Stefano by Grand Duke Cosimo III in exchange for about 108,00 “scudos”. This administration continued with important improvement interventions connected with the policy of reclamation by alluvion, applied by Grand Duke Pietro Leopoldo up until 1809, when the Order of Santo Stefano was dissolved because of the Napoleonic abolition of all the monastic institutions. The estate passed to the French domain.

With the return of Grand Duke Ferdinando III of Hapsburg-Lorraine in 1814, Montecchio – together with the other eleven estates – became a part of the state of the Possessions of the Crown in Valdichiana. This was administered by a special body located in Arezzo known as the Economic-Hydraulic Administration of the Valdichiana, until it was sold to private individuals by the government of the Kingdom of Italy between 1863 and 1864, as were all the other estates.

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