The earliest known mention of Palazzo Pretorio dates to 1164, when a certificate from Federico I Barbarossa named it as the established residence of the Alberti Counts, a noble family that held numerous estates along the Arno River in the Valdelsa and Val di Pesa areas.
Around the end of the 13th/beginning of the 14th century, Certaldo definitively came under the influence of Florence, and the Palazzo was confiscated from the Alberti Counts, and transformed from a feudal castle into a public building.
As early as 1415 (a date found on one of the numerous coats of arms present), Certaldo had a resident Vicario, a Florentine magistrate tasked with administering justice in the Valdelsa and Val Di Pesa, who had power over the smaller towns in the area as well. This was the beginning of the period of Certaldo’s greatest splendor, the Vicariato.
During the 18th century, the territory of the Vicariato of Certaldo was progressively reduced, and was definitely suppressed in 1784. After that date, the palazzo was emptied of all its décor and furnishings, and then sold to be converted into private residences – 15 of them in fact, each of which had 2 or 3 rooms. The destruction was halted in 1890 when the community of Certaldo re-acquired the palazzo and work began on the restoration and refurbishment of the entire building.
The now-deconsecrated old church alongside the palazzo conserves 15th and 16th-century frescoes and sinopias, as well as the very important Tabernacle of the Condemned (ca. 1464-65), attributed to Benozzo Gozzoli. The Tabernacle was originally set on the bank of the Agliena River, where prisoners condemned to death were taken before their execution for a final prayer. For reasons of conservation, the frescoes were detached and moved into the church, but the original structure of the Tabernacle is still visible today near the bridge along the Agliena, in the lower part of the town.