The Oratory of the Santissima Annunziata of Montescudaio was erected around 1450-80, was completely renovated. The current facade dates back to the thirties of the twentieth century and was enriched by two stone columns surmounted by capitals. Also the main door was embellished by two columns surmounted by small eardrum to frame detected, interrupted in the central part, where it welcomes a bas-relief depicting the Annunciation. At the top there are the busts in terracotta of San Sebastiano and San Rocco.
Inside the tabernacle, embellished by the inlay of precious alabaster, is surrounded by three orders of steps which rise in the central part, giving origin to the recess containing the statues of the Annunziata and the angel of the Annunciation in painted terracotta, kept by 1598 in the oratory, which are at the origin of a fervent Marian devotion. At the center of the nave is the tomb of Blessed registrars, who died in 1851, important landowner of the area and the renowned surgeon.