One of the most highly venerated Marian shrines in Florence, the church was founded in 1250 as the Oratory of Cafaggio, by the Seven Holy Founders of the Servite Order. These noble Florentines, having been vouchsafed a vision of the Virgin, retired from the city to a wild hermitage at Monte Senario, north of Florence.
The history of their new Oratory is closely connected to the cultus of a painting of the Madonna, showing the Annunciation, which is still preserved in a chapel at the entrance to the basilica. Popular piety relates that the fourteenth-century artist, a certain Friar Bartolomeo, was having difficulty in painting the face of the Virgin, when he fell asleep; on waking he found that the fresco had been finished by angelic hands. The religious fervour aroused by this reported miracle led to the church being enclosed by houses in the 14th century as people wanted to be near the place where the miracle had happened.

The present structure took shape between 1444 and 1477, when Michelozzo began the tribune with its radiating chapels, later finished by Leon Battista Alberti.
Towards the end of the 15th century the height of the nave was increased. The church was consecrated in 1516.
Outside, above the central arch of the portico, built in 1601 by the architect Giovanni Battista Caccini, there are traces of frescoes painted between 1513 and 1514 by Pontormo, and the central doorway is surmounted by a mosaic of the Annunciation by Davide Ghirlandaio (1509).

From the portico we enter the cloister, known as the cloister of the ‘Voti’, because it used to be filled with votive pictures and wax statues decorated with precious ornaments.
Today it is famous especially for its magnificent frescoes: the earliest is Alesso Baldovinetti’s Nativity, painted in 1460; Cosimo Rosselli’s Calling of St. Philip Benizzi dates from 1476; the other episodes from the life of the Saint were painted by the young Andrea del Sarto in 1510.
The Life of the Virgin was narrated in the second decade of the sixteenth century by the youngest and most promising artists of the day: Rosso Fiorentino painted the Assumption, Pontormo the Visitation, and Fraciabigio the Betrothal of the Virgin. Andrea del Sarto, who had already worked on the St. Philip Benizzi frescoes, painted between 1511 and 1514 the Nativity of the Virgin and the Arrival of the Magi.

The breath-taking interior, with arches and piers sheathed in coloured marble (16th and 17th century), has a golden ceiling decorated between 1664 and 1670 to a design by Baldasarre Franceschini, known as Volterrano, who also painted the canvas of the Assumption.
High up between the windows there are panels and medallions, painted with Miracles of the Annunciate by 17th-century artists.
To the left of the entrance is the Chapel of the Most Holy Annunciate, where the highly venerated image of the Virgin is preserved. The elegant tempietto which encloses it was designed by Michelozzo and built by Pagno Portigiani in 1448; the small oratory next to it has a panel of the Holy Face by Andrea del Sarto.

The many side chapels in the nave are mainly of the 17th and 18th century, such as the Feroni Chapel, by Giovan Battista Foggini and others, a jewel of the Florentine Baroque.
The Tribune has nine chapels which were completely transformed in the baroque period. Andrea del Castagno, one of the principal exponents of the Florentine renaissance style, was especially active in Santissima Annunziata: one of his frescoes is of St. Julian, in the Feroni Chapel, another is of the Holy Trinity with St. Jerome, in the adjacent chapel.

Leaving the church by the door at the end of the nave on the left, we enter the Cloister of the Dead, built around 1453. Above the door is the celebrated fresco of the Madonna del Sacco (1525) by Andrea del Sarto. In the other lunettes there is an interesting but very damaged fresco cycle on the Servites of Mary, painted in the early seventeenth century by Bernardino Poccetti and other artists of his time. Also in the Cloister is the Chapel of the Company of St. Luke, where the Confraternity of Painters had its headquarters in 1562 (before being moved in 1563 by order of Cosimo I to the Academy of the Arts of Design).
The ceiling was frescoed with the Assumption by Luca Giordano, and the high altar has a canvas by Giorgio Vasari showing St Luke painting the Virgin. On the other walls are works by Bronzino, Pontormo and Santi di Tito.