Along the eastern side of Asciano’s historic center lie the remains of the ancient Porta della Pieve (Gate of the Parish Church), formerly known as Porta Massini (Massini gate) and, in the 19th century, as Porta Lauretana (Lauretana gate) or Porta per Loreto (Gate to Loreto), due to its location along the Lauretana road.

The original structure was severely damaged during World War II, and today only a few masonry elements remain: the right jamb, a springing corbel, and part of the arch ring, with well-cut travertine blocks still bearing visible marks from traditional stonecutting tools, such as the toothed chisel and ribbon chisel.

Some inscriptions that were once part of the structure have since been relocated to the adjacent section of the wall (designated as CF 1.15).

Among the surviving inscriptions is a much older and nearly illegible stone plaque, which attests to the antiquity of the site and enhances its historical significance.

The name "Porta Massini" likely derives from a family that lived nearby or played a role in the management or renovation of the structure.

On February 5, 1952, during the feast day of Asciano Patron Saint, an extraordinary celebration was held, culminating in the inauguration of the marble statue of Saint Agatha, placed on the remaining section of the arch of the destroyed gate. The statue still stands today, overlooking the town’s main entrance and serving as both a visual and spiritual symbol.

The work was commissioned by Proposto Sadotti and carved by stonemason Luigi Rossolini, on behalf of the Società Paradiso of Serre di Rapolano. The sculpture was based on a plaster model previously created by Giovanni Magi, nephew of the renowned sculptor Luigi Magi.