Santissima Annunziata, Ascoli Piceno, Medieval church in Ascoli Piceno, Italy.

Santissima Annunziata is a former Roman Catholic church in the Parco dell'Annunziata in Ascoli Piceno, part of a complex that includes two cloisters, a former convent and a refectory. The larger 14th-century cloister is square, with a portico of octagonal pilasters supporting a loggia above; the smaller cloister has a 15th-century well at its centre. An eight-arch portico precedes the complex.

The site housed a hospital until 1250, when Peter of Verona had it entrusted to Augustinian nuns, who built the small church and the square 14th-century cloister with octagonal pilasters. Nuns of the rule of Saint Monica took over in 1444, and from 1481 to 1861 the Observant Franciscans of Ascoli held the convent and church. From 1882 the buildings housed Italy's first Practical School of Agriculture, from 1933 the Conservatorio Regina Margherita, and they now hold the Unicam School of Architecture and Design.

The church holds deep meaning for the city because of an ancient freedom granted by papal authority that is celebrated here each year on March 25th through processions led by residents. This annual gathering reflects how the place remains connected to local identity and memory.

The building serves active functions today and visitors should check accessibility in advance or inquire about special events that may occur. The site is easy to reach on foot and the layout with its two courtyards is spacious and welcoming for exploration.

On the west wall of the former refectory hangs a 1519 lunette by Cola dell'Amatrice, "Christ's Climb to Calvary", from his early period. Napoleon's army damaged it and it was restored in the first half of the 19th century. The complex also once held Crivelli's Annunciation, now in London's National Gallery.