The conventual complex, dedicated to the Florentine Carmelite St. Maria Maddalena de’ Pazzi, who had such an influence on 17th-century spirituality, was originally founded in 1257 and dedicated to St. Mary Magdalen ‘delle Convertite’, in a place where there was already a house for ‘penitent’ (or ‘converted’) women who followed the Rule of St. Benedict. The Cistercians from Badia a Settimo, who took over control of the convent in 1322, moved here in 1442, at the invitation of Pope Eugenius IV who sent the Convertite away to San Donato in Polverosa. The convent in Borgo Pinti was rebuilt between 1481 and 1500; paid for by Bartolomeo Scala, it was designed by Giuliano da Sangallo, who devised the innovatory Ionic porticoed quadrangle in front of the church.

The aisle-less interior has six deep chapels on each side of the nave, in white plaster with beautiful carved arches in grey pietra serena, and was harmoniously decorated between 1480 and 1530 with altarpieces by artists such as Botticelli, Perugino, Lorenzo di Credi, Domenico and Ridolfo del Ghirlandaio, and Raffaellino del Garbo, which unfortunately were moved elsewhere during the rearrangements of the 17th and 18th century. They were replaced by new ones, by minor masters such as Carlo Portelli, Alfonso Boschi, Domenico Puligo, Giovanni Bizzelli, Santi di Tito, and Francesco Curradi.

The monumental fresco of the Crucifixion, painted by Pietro Perugino in 1493-1496, was commissioned by Dionisio and Giovanna Pucci, members of two aristocratic Florentine families.

The decoration takes up a whole wall, divided by the ceiling vaults and the painted architectural arch elements. The harmonious and luminous scenery contributes to decreasing the emphasis of the drama represented by the scene, that reflects the typical serene and meditative attitude of the artist. The fresco portrays the Virgin Mary and John the Baptist, at the foot of the cross. The other personalities were chosen because they had a very special meaning for the monks living in this convent.

“Maddalena” is the saint to which the church was originally dedicated in 1257; St. Benedict is the father of western monachism, while Bernard de Clairvaux (represented in a white garment) is the famous theologian of the early years of the Cistercian order. The three trees with slim trunks and thick foliage behind the figure of St. Bernard are perhaps a symbol of Trinity.
A century later, Bernardino Poccetti frescoed the Chapel of St. Mary of the Lily, to the right of the entrance to the complex