The founding legend of Villa Pozzolo begins with kidnapping, human sacrifice, two beautiful maidens and two brave noble men: the young Figline was kidnapped by the villain Gambasso only to be saved by the noble man Ajone and, of course, they married and founded the village Montaione. Until today there’s a fierce competition between the neighbouring communes Montaione and Gambassi.

Years later the descendants of Ajone and Figline were attacked and in a throwback to their heathenish ways decided to sacrifice their most beautiful maiden, Filli, who was – history repeats itself - saved by a brave knight who sacrificed a calf in her stead. He loved her so much that he kept calling her ”Fili Cara”. It need not be mentioned that Filli and her knight married and their many offspring were henceforth called Filicaja. This legend, which was told by the grandson of famous painter Michelangelo Buonarroti is the founding story of Montaione and of the family Filicaja who previously owned Villa Pozzolo.
In real life Ser Giovanni di Simone Filicaja purchased the castle of Figline (later Villa Filicaja) - another property of the Filicajas in 1452. Another story suggests that the hamlet was given to the Poet Vincenzo da Filicaja (1642-1707) by Grandduke Cosimo III di Medici but Vincenzo actually already owned the land at the time. He loved to stay in the countryside and away from the court as long as he could because he didn’t want to loose his intellectual independence. At the same time he was friends with Queen Cristina of Sweden who financed the education of his two sons. “Not ambition but necessity” brought him to accept numerous important positions offered to him by Grandduke Cosimo such as Governor of Volterra, and later Pisa, as well as senator of ethics in Florence.

The beginnings of Villa Pozzolo as a building are not entirely clear. It is possible that settlements already existed here in Etruscan times; a castle with a courtyard was first mentioned at the site in 1005 and again in 1113. Transformed many times over the following centuries there is little left of the castle except probably some blackened bricks and the thickness of some walls. “Pozzolo” means “little well” or “little palace”. The existence of a water filled subterranean chamber under the house supports the first meaning. The bigger part of the roughly u–shaped building was erected in the early 19th century with nearly the whole ground floor dedicated to the storage of wine and olive oil. The living quarters for the family on the “piano nobile” were much more elaborate with painted beams, walls and frescoes. Two painters, the Italian Giuseppe Bezzuoli and the English romantic painter George Augustus Wallis were commissioned in the 1820s and 30s to paint landscape murals for the walls of the south facing first floor drawing room, which are still preserved today.
​Another interesting feature is the memorial stone for the horse Caro Morinho, which saved its owner from many perils. During the second world war the Villa was occupied by the German army with canons posted in front of the house. In the 1970s most parts of the villa were turned into holiday apartments.
The Filicaja family used the house less and less and the last 10 years, before the villa changed owners, it stood completely empty.

In 2012 the von Glasow family bought Villa Pozzolo and refurbished it for next five years, aiming to rebuild the house while restoring its character. Many partition walls, which were erected in the 1970s were pulled down and old structures such the loggia in the courtyard were made visible. The rooms were painted partly in original colours that were found under the plaster and another mural was discovered, still waiting to be restored. 
The von Glasows rent out the villa with a 21st century take on 19th century hospitality. They hope to use it to help people learn, teach, forge friendships and fulfill their dreams.