The origins of the Pieve di San Leonardo are not known, but the structure of the Bell Tower suggests that it was born as a chapel of the Conti Guidi Castle, the family that dominated the surrounding lands from the 11th to the 13th century. The church, originally with a single hall and circular apse, has undergone numerous renovations over time, including the portico that connects it to the Villa. In 1827 the building finally took on its current appearance with three naves. Inside the church there are artworks of considerable value, such as the canvas attributed to Ghirlandaio called 'Madonna Enthroned with the Child between Saints Paul and Leonard', a wooden Crucifix by Giambologna from the 14th century, and the Baptismal Font in glazed terracotta attributed to Giovanni della Robbia. The painted scenes refer to the cycle of the Stories of the Life of St. John the Baptist and must be observed with particular attention, to catch details such as animal and vegetable figures hidden in the seabed.

Right next to the Medici Villa of Cerreto Guidi, from which the Grand Duke's family could directly access the religious services, there is the Pieve di San Leonardo, which already existed in medieval times as a chapel in the castle of the Guidi Counts. Today only the crenellated bell tower, which looks more like a tower than a religious building, recalls the medieval origins of the church. Since 2014 the wonderful bell tower is open to the public, but only during some particular events. From up there you can enjoy a breathtaking view that includes an incredible portion of Tuscany.

Inside the Pieve di San Leonardo there are various artworks: 'The Madonna Enthroned with the Child between Saints Paul and Leonard' by the Ghirlandaio, the painting depicting Saint Leonard by Cristofano Allori, 'The apparition of the Madonna to San Bernardo' by the painter Giovan Battista Volponi from Siena. Among these artworks three wooden crucifixes stand out, placed in three different points of the church: the Crucifix by the Master of Camaiore (first half of the 1300s), the Crucifix attributed to Andrea Ferrucci (late 1400s), the Crucifix by Giambologna (1500). Thus a transversal artistic path is created in which the theme of the Calvary of Christ is elaborated over time, from the Late Middle Ages to culminating in the Renaissance.

Baptismal font in glazed terracotta made by Giovanni della Robbia in 1511. It has a hexagonal base and in each of the six faces there are reliefs depicting the life of John the Baptist. The influence of painting is clearly noticeable: there is an unequivocal reference to the stories of the Baptist by Ghirlandaio in Santa Maria Novella at the so-called Parato of San Giovanni by Antonio del Pollaiolo; a more nuanced link also with Verrocchio's famous Baptism of Christ. The client family was the Rucellai family, of which two members were parish priests of the church of San Leonardo; for this reason their coat of arms is recurrent in the reliefs.