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The monumental center of Pienza is the Piazza Pio II, living example of the utopian ideal city designed by humanists architects of the fifteenth century. The square contains all the main buildings of the village, the Cathedral, the Bishop's Palace, the Palazzo Piccolomini, Municipal Palace, the Palazzo Ammannati and a fine 15th century well.  

The highlight of the square is the facade of the Cathedral of the Assunta, that was built between 1459 and 1462. While the rest of the building is in tufa, the facade is in travertine with a double order of columns and three portals. In the great tympanum is the coat of arms of Pio II. The inside is with three aisles and contains five tables of the 15th century senese artists of an altar attributed to Bernardo Rossellino.

To right of the Cathedral is Palazzo Piccolomini, the more important palace of Pienza, masterpiece of Bernardo Rossellino, it was built between 1459 and 1462. It represents a copy of Palazzo Rucellai in Florence planned from the same Rossellino, it has a square plan, flat ashlar-work with pillars of Tuscany order and two floors of double mullioned windows. Inside of the palace there is a beautiful square courtyard with loggia and a garden with beautiful panorama on the Val d' Orcia. To an angle of the palace it's the 15th century well with two columns with capitels.

To the left of the Cathedral is the Episcopal Palace or Borgia, that it has two floors of Guelph windows and was restructured from the cardinal Rodrigo Borgia (future Pope Alexander VI). On the opposite side of the square in comparison to the Cathedral are the Communal Palace (with porch of ionic order, with a floor to four double mullioned windows and a beautiful tower finished in 1599) and Palazzo Ammannati.