The former hospital of San Giovanni Valdarno faces the main thoroughfare to the historic center and marks its entrance point. One of the projects part of the city’s strategic plan, following the construction of a new hospital designed by Vittorio Gregotti, the conversion for residential and commercial use of the area entailed demolishing the old building and reconfiguring the spaces surrounding it. The design envisioned an urban model based on the principles of closing and bounding while simultaneously opening and making accessible. This concept is epitomized in the architectural conception of the square. Through carefully planned openings, the design gives a new visual perspective on the pedestrian thoroughfare, which leads to the historic center, and of which the project is a natural extension. A large projecting portico extends along all sides of the buildings’ perimeter. The façades call a city block to mind with the sight of a sequence of urban facades, with the staggered layout and varying heights of contiguous structures of a varied sequence of buildings and roofs, moving up to the top of a tower, in a medieval type organization of space.