The borough of “Villa Serignana” came into being during the 1200’s. The land was the domain of the Counts Guidi, noble Ghibellina family. The Counts Guidi’s family owned lots of land in Tuscany, however their main seat of power was in the Castle of the nearby Casentino.
The borough of Serignana as well as the castles and the district of S. Godenzo, became a property of the Counts Guidi di Modigliana, in particular to the branch of the Counts of Porciano after various imperial assignments which started from the year 1191, first with the emperor Arrigo VI, then in 1247 with the emperor Federico II.
In 1304 the counts gave the rural “statutes” to the Villa of Serignana di Sopra. Through the various happenings that have witnessed the lineage of the Counts Guidi being adverse to the Signoria of Florence, one must remember the important convention that took place in June 1302 in the Benedictine Abbey of S. Godenzo, amongst the Florentine exiles of both important families: the Ghibellini and the Guelfi “of the parte bianca” which included Dante Alighieri. At this convention, in a deed stipulated by the lawyer Giovanni di Buto d’Ampignana, the participants agreed to re-conquer Florence and secure its future, financially and with manpower in the case of war. This convenction is remembed every year during the event "Dante Ghibellino" that is place of an important convention of Dante's research.
In 1356, count Guido Domestico sold Serignana and all its lands to the Signoria of Florence for 2650 gold florins.
On the 28th April 1478, two days after the Pazzi's conspiracy that took place in Santa Maria del Fiore in Florence to the detriment of Lorenzo dei Medici (The Magnificent), where his brother Giuliano died, Iacopo de’ Pazzi, head of the family hence the name of the conspiracy, was captured together with nine of his accomplices. On the same evening from Serignana Iacopo de’ Pazzi was brought back to Florence and there, just before midnight was hanged together with seventy fellow conspirators from the railings of the windows of the Palazzo della Signoria.
In this place in 1421 was born the great renaissance painter Andrea del Castagno (1421-1456). The village of Castagno d'Andrea get its name from the painter.
Through recent world history and, in particular the last war (world war II) ,Serignana escaped intact even though S. Godenzo and Castagno d’Andrea both in close proximity were totally destroyed.