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On the front side, along the eastern side of the square, the Dei family built a Palace of three floors with a beautiful covered terrace by Cronaca, who also designed the vestibule of the sacristy of the Church of Santo Spirito.The Palace, whose original facades were decorated with white graffiti on an iron-grey background - perhaps by Andrea del Sarto - was later purchased by the Guadagni family and still bears their name.

Before the 16" century, that is before the building of some palaces, the eastern side of the square was taken up by modest dwellings. The ground floors often had wooden shelves and benches around the The square was often used to celebrate religious festivities, as for instance during Whit Sunday to commemorate the descent of the Holy Spirit on the Virgin and the Apostles.

To celebrate this event, fires were lit in the square, in the Church and on the bell tower. St. Augustine's feast day was celebrated with tournaments, a palio in the neighbouring streets. A solemn procession was held on the Patron Saint's Day. In November, the square was used for the celebrations of the "Gran Festa della Palla Grossa ", which probably was a football game. In addition to official commemorations and festivals, the square was also used for several games and more specifically for the famous game of "Pallottole", that became so popular that the authorities decided to forbid it.