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The Castle of Montauto was first built as a military base, in the year 964, to control the merchant traffic between Pisa and Arezzo. In the following centuries it enjoyed mixed fortunes until the middle of 16th century when it was transformed into a villa by the architect Domenico Baccio D'Agnolo. The castle despite its large dimensions, does not take away from its surroundings since it is surrounded by a dense forest of Cypress and Oak trees which extends well beyond the perimeter of the ancient walls which where once witnesses to gruesome battles between the Guelfi and Ghibellini and to even more violent attacks between the Bianchi and Neri.
 
The chapel of Montauto is half hidden by vegetation and conserves even today its original primal aspect of simplicity and austerity, thanks to restoration work performed by Cavalier Busi during the nineteenth century. Inside the church it is possible to admire a valuable mural which is believed to be the work of the school of the artist Giorgio Vasari. Above the main entrance there is a relief in terracotta, by the Robbiana school, representing Saint Lucia.
 
Subsequently Montauto became the property of the Niccolini family which continued to enlarge and decorate the castle with precious murals attributed to Volterraio and Giacinto Gemignani. This important and historic abode is an interesting monument which encompasses aspects of medieval, renaissance and baroque art. Despite changes in ownership over time, the castle stills maintains today most of its original character as a strongly fortified and majestic castle.