This church is at the western end of the decumanus maximus of the ancient Surrentum, in the area where there was a temple dedicated to the Goddess Cybele (whose marble altar is kept in the Museo Correale, the town's museum).
The building of the temple is attributed to the Sorrento nobleman Giovanni Ammone between 1284 and 1299.
It was annexed to the monastery of the Padri Agostiniani (Augustinian Fathers) of the Congregazione di San Giovanni a Carbonaro di Napoli (Congregation of Saint John of Naples), the oldest religious house apart from the Benedictine Saint Renato outside the city walIs. According to the historian Giulio Capaccio (Historiae Neapoletanae, 1771), inside the church there was an ancient sepulchral inscription of 1341 for restoration work carried out by the noble Sorrento families.
In 1393 Isabella Sersale, niece of Pope Boniface IX, was buried here, but other Sorrento noble people were also buried here, as can be seen on the plaques in front of the altars that were patronised by the noble Sorrento families. In 1714 the church underwent radical architectural changes and in 1768 the Cardinal of Naples, Antonino Sersale, built at his own expense the façade in grey tufa, on which the family's coat of arms is still visible. In 1864, on the northern side of the church, the main street, Corso Italia, was constructed and took away a part of it. Following this transformation, the painting The Annunciation of Mary was taken down and put in the sacristy. The throne was placed near the 18th century statue of The Madonna with Child, whose festival is on the Sunday following that of Saint Augustine (28 August). The ceiling is painted on canvas with a centrally-placed painting by Filippo Andreoli (18th century), depicting the Madonna with Child, giving the sacred belt to Saint Augustine and other Augustinian saints. In the 1930s the side walls of the church were covered with mosaics and multi-coloured marble.
The temple of the Santissima Annunziata is also the site of the ancient Archconfraternity of Saint Monica.