The first reliable records of the existence of a royal chapel located at the foot of the Pietrarossa rock date from between 1220 and 1250, during which time the church - identifiable as Santa Maria degli Angeli - was entrusted with the care of the souls of the city of Caltanissetta. In 1239, a decree issued by Frederick II assigned the church the role of parish seat of the city.
According to tradition, the dedication to Santa Maria degli Angeli is due to the discovery, among the ruins of Pietrarossa Castle in 1600, of a wooden panel depicting the Virgin on a throne with the Child, surrounded by angels. More likely, the painting - whose origins in Pietrarossa are not confirmed - was commissioned by the Moncada family, whose coat of arms appears at the bottom of the painting, on the occasion of the arrival of the Franciscans, known for their devotion to Our Lady of the Angels. On September 18, 1601, Lady Luisa de Luna e Vega Moncada, the powerful Countess of Caltanissetta, donated the large complex to the Minor Friars, who then built their convent and made restorations and improvements to the ancient 13th-century church.
For the construction of the convent, stone was mainly used from the ruins of Pietrarossa Castle, which by then was already in an advanced state of decay. Additional stone was extracted from the rock on which the manor stood, which until the 19th century served as a quarry for the material used to build the city's main structures. Following the suppression of the religious orders in 1866, the church was stripped of its paintings, sacred furnishings, wall decorations, and altars; the painting of the Madonna was transferred to the Collegio di Maria, where it remains today.
The church has a single nave with a semi-octagonal apse. The convent, with two levels, is composed of a perfectly square structure enclosing a cloister. The eastern side extends toward Pietrarossa Castle, whose rock, along with the boundary wall of the cemetery below, creates a second irregularly shaped courtyard. At the center of the cloister is a large water cistern, while a smaller one is located in the second courtyard, next to the dormitory building.
Recently restored, the convent complex has been returned to public use, freed from the superstructures added due to the improper uses to which it was subjected over the past 150 years, which had obscured the original plan. The church, whose decorative layout had been completely altered after being converted into military barracks, has been restored to its pre-confiscation state. The ground floor openings have been closed, and the medieval lancet windows and a secondary entrance opening directly onto the cloister have been brought back to light.
The splendid main entrance portal, in sandstone and facing west, is the building’s most distinctive feature. Four small columns with capitals support a pointed arch decorated with zigzag motifs, surrounded by foliage ornamentation marking the outer edge. The portal is closed by a massive wooden door, also recently restored.
The north façade, entirely of exposed stone, shows the remains of another portal bearing the same characteristics, to the left of which is a pointed arch frame enclosing a rampant lion. The current opening is elevated above street level, which was rebuilt in the second half of the 19th century to allow access to the cemetery. It was due to the excavation for its construction that a substantial supporting wall was built along the base of the church, visible along the entire length of the north façade.
Inside, the recent restorations have revealed the remains of an altar dating back to around the 16th century, with a frame decorated in polychrome stucco featuring geometric motifs, as well as the niche that once contained the statue of Saint Paschal Baylón. The crypt that extended the entire length of the church was also discovered and cleared of the earth that had filled it, containing “seat-type” colatoi under the apse area.