The church stands on the pre-existent oratory of the Servi di Maria (1235) which was built around the miraculous image of Our Lady of the Annunciation by seven young noblemen who decided to take monastic vows and give up worldly pleasures. As a further sacrifice, they later founded the Monastery of Monte Senario, above Fiesole.Michelozzo built the First Cloister in the mid 15th century. The main body of the Church, started in 1440 by Michelozzo and Pagno Portigiani, was later altered by Alberti, who created the impressive Tribune that can be seen on the righthand side.
Three separate environments can be reached from the plain facade, decorated with the coats of arms of Pope Leo X dei Medici frescoed by the young Pontormo : the Chapel dei Pucci or of San Sebastiano on the right; the large Cloister dei Morti on the left, with frescoes also by Andrea del Sarto (the Madonna of the Bag); and the First Cloister or little Cloister dei Voti in the centre, frescoed throughout by masters of the Florentine Mannerist school of the early 16th century: Rosso Fiorentino, Pontormo, Franciabigio e Andrea del Sarto, who painted the face of the Virgin as a really faithful portrait of his wife, Lucrezia del Fede who apparently, according to Vasari was not faithful at all.

The interior of the monument, designed by Alberti but later covered by rich baroque decorations, consists in a single nave covered by a large cupola. The elaborate Baroque ceiling was carried out by P.Giambelli on a design by Volterrano (XVII cent.). The side chapels contain a great many works of art: frescoes by Andrea del Castagno, an Our Lady of the Assumption by Perugino, a Resurrection by Bronzino, sculptures by Giambologna and, in the transept, a marble Deposition by Baccio Bandinelli whose self-portrait can be seen in the face of Nicodemus in the vault.
Inside, on the left, one can see a little marble temple designed by Michelozzo (1448-61) in honour of the fresco of the Annunciation; this is still greatly worshipped and is exposed to the faithful on March 25th (Assumption Day) every year (which was also the date of the Florentine New Year for many centuries)

According to legend, the anonymous artist who painted it fell asleep after having completed the angel but his sleep was disturbed by his fear of not being capable of portraying the Virgin better than the angel he had just painted. When he awoke he was surprised to find that the fresco had been completed by a supernatural hand. Since popular tradition attributes this painting with miraculous virtues, young married girls still go to the Church of the Annunziata immediately after the marriage service to offer their bridal bouquets to the Madonna of the little Temple.
The face of Christ in the relic is by Andrea del Sarto. Apart from the works mentioned above, the chapels in the lefthand nave contain the Holy Father with St. Jerome and the Holy Trinity by Andrea del Castagno, who with rude violence interprets Masaccio 's lesson in perspective at the Carmine.

The Cloister dei Morti leads into the Chapel of San Luca, the patron saint of painters, where Cellini, Pontormo, Franciabigio, Bartolini and other masters are buried. Annual exhibitions of painting by contemporary artists were held here in the 16th-18th centuries.