The church of Santa Maria al Prato was built, at the initiative of the Dominican friars of Santa Maria Novella, starting in 1304. In the 16th century it underwent profound transformation, and in 1631 it became the seat of the Arciconfraternita della Misericordia di San Casciano. In the first half of the 17th century the church was renovated in Baroque style by inserting four altars along the side walls, owned by wealthy families such as the Bambagini, the Ninci and the Borromeo. During World War II the church was severely damaged, requiring major restoration.
Inside, on the left wall, is a Madonna and Child Enthroned with Sts. Catherine, Peter, Magdalene and Bartholomew the Apostle by Fra' Paolino da Pistoia, dating from 1518, while the Madonna with Child by Ugolino di Nerio is placed over the main altar.
Above the doors to the sacristy we find Saint Francis and Saint Peter, the remains of a polyptych by Ugolino di Nerio dismembered and now lost; beside these works are two 17th-century paintings portraying Saint Thomas Aquinas and Saint Lawrence, the work of Rutilio Manetti.
On the right wall we find what is probably the church’s most precious artwork, the Pulpit commissioned of Giovanni di Balduccio by the Bonaccorsi family in the first decades of the 14th century. Beside it is a painted cross unanimously attributed to Simone Martini, dating from the third decade of the 14th century.