With the purchase of this Estate in 1592, the Gondi family extended its property in Chianti Rufina, an area famed since the Renaissance for its production of fine wines. The Gondi have thus been wine producers for over five centuries.

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One of the Gondi family’s most important estates is the Villa Bossi at Pontassieve, which has belonged to them since 1592. Before this time, the land formed part of the Quona property near San Martino in the Commune of Pontassieve. On it stood a castle, destroyed in 1143 by the Florentines during the war against the Counts of Guidi, of whom the Da Quona were vassals. The villa is situated near the Frescobaldi estate, Poggio a Remole, formerly owned by the Albizi, on the slopes of the Bardellone Hill. In 1427 the Bossi Villa belonged to Bartolomeo di Andrea di Domenico a ‘forzerinaio’. In 1546, when the Tolomei brothers’ property was divided, the residence went to Paolo, who left it to his son when he died in 1558.
The residence remained in the Tolomei family until 1587, when it was consigned in usufruct by Paolo to his mother, Costanza di Daniello degli Alberti, who had been left a widow. The villa remained in Costanza’s hands until 1592, when it was sold by Paolo’s debtors to Bartolomeo di Bernardo Gondi for 7,500 lire.
Bartolomeo Gondi thus bought the manor house with ‘field, chapel and eight farms annexed to it’, adding to this property a neighbouring farm he had owned since 1516. He was able to buy the villa thanks to a legacy he had received from Antonio Gondi, in a will notarized in 1591. The will specified that, for any property bought, the sales contract must stipulate that it could be left in future only to other members of the family.
The ‘house of the master and worker’, with its annexed farms, bought by Bartolomeo in 1592, was then left to his sons Alessandro and Bernardo.
From 1629 to 1638 the Villa Bossi belonged to Bernardo Gondi’s two sons, Antonio and Francesco. The latter wrote his will in 1678 in favour of his own sons, and confirmed that the property would always be left to Gondi descendants in the male line, on condition that they resided in Florence.
In the early 16th century, not far from Bossi, at the centre of a vast terrain that, from the right side of the Sieve River, slopes up the hill above the town of Pontassieve, the Gondi also built the neighbouring Villa di Grignano, which was sold in 1972.
This villa was officially listed as one of the Gondi estates already in 1509, when it belonged to Antonfrancesco Gondi, along with four farms situated in the Popolo di San Niccolò a Vico, in the Podesteria di Ponte a Sieve.
In the second half of the 18th century, with Niccolò Antonino Gondi, the Villa Bossi was extensively remodelled, enlarged and embellished with splendid baroque decorations, while its small chapel became a real church with three altars, a great organ operated by a bellows, two choir stalls at the sides, one for the family, the other for the domestics, and a spacious sacristy at the back. In this church are the tombs of every member of the Gondi family who has owned the villa from that time on. The appearance of the great residence is known to us from a drawing by Raffaello Paganelli (1744-1810). For the experience and professional skill acquired over the course of years, Paganelli was called ‘most expert at drawings and views of buildings’.
The two projecting bodies of the villa surrounded a central courtyard open toward the valley, which was later converted into a drawing room. A double ramp staircase, no longer existing, led to the piano nobile above.
A chapel with pediment decorated with wavy scrolls enhanced the image of the entire architectural complex, along with a painted olive-mill simulating a wooden structure. An inventory of the Bossi estate, along with the Panche and Camerata properties, was compiled on January 28, 1795, the day when Niccolò Antonino Gondi died, then to be buried in the chapel of his Villa Bossi. On September 22, 1798, Lamberto di Pier Matteo Frescobaldi sold to the heirs Amerigo Antonino and Francesco Gaetano, the brother and son of Niccolò Antonino Gondi, ‘a house with a piece of land and a farm called Stieto with a worker’s house situated in the Popolo of San Giovanni Battista at Romole’, which went to augment the property.
Over the course of the 18th century the Gondi family also remodelled the Villa di Grignano, bordering on the Bossi property.
In the General Land Registry of Tuscany for 1832, the Villa Bossi was listed among the estates owned by the Gondi brothers.
The Villa Bossi assumed an increasingly important role for the family, and between 1878 and 1884 it was remodelled and enlarged by closing off the central courtyard that had been open to the valley. This was done at the initiative of Francesco Gondi’s young widow, Maria de la Bruierre, a French noblewoman who, unsatisfied with the Florence of the day, preferred to spend much of her time in her country villa with her two children, Carlo and Maddalena. In addition to creating the central drawing room, she added another floor to the villa, with servants’ quarters and a great wardrobe. She also had the cellars enlarged by building a great room under the garden equipped for wine-making, entered through a long stairway leading down from the rooms where the wine was aged in oakwood barrels and barriques. She had the whole cellar partially covered with soil, to ensure a more stable temperature in both winter and summer; adorned a great park with Cedars of Lebanon and yew trees; and laid out a formal Italian garden in front of the villa. With these large-scale projects, the villa lost its previous austere look, and still today reflects a certain French taste. Over the centuries, the Gondi family had influenced Parisian and French architecture in general, but in this case the reverse was true. Carlo was succeeded by his son Giuliano, and then by Bonaccorso, who enlarged the property by annexing the adjacent Quona estate. At present, the Villa and the Estate belong to Bernardo and his sister Donatella.
The wealthy Gondi family will thus continue to hold a prominent place in Florentine society. Its latest descendants, Marchese Bernardo and his wife Vittoria, with their sons Gerardo and Lapo, are still today the owners of Palazzo Gondi in Piazza San Firenze. And the family still produces Chianti Rufina wine and Extra-Virgin olive oil on their ancient Bossi estate at Pontassieve and their Volmiano farm at Calenzano, on the slopes of Monte Morello.