The original square was a smaller space than the current one, located between the ancient parish church of Santa Maria (elevated to cathedral status in 1138) and the early town hall.

Major urban restructuring occurred from the late 13th to early 14th century, inspired by Siena's Piazza del Campo, with key public buildings facing the square.

The square was redesigned by Grand Ducal engineer Angiolo Cianferoni, who created a circular pavement with stone posts, chains, and benches.

In 1956, Piazza Dante underwent substantial changes: the stone posts, chains, and benches were removed, the paving was replaced, and a parking lot was created in the center of the square, extending radially around the statue of the grand duke.

Designed by architect Lorenzo Porciatti, with adjustments made during construction by Guglielmo Calderini, the building is in a Gothic-Revival style reminiscent of Sienese medieval architecture.

Sculpted by Luigi Magi [it] in 1846, the statue depicts Leopold II, Grand Duke of Tuscany, dressed in the style of an ancient Roman.

[6] The Grand Duke is shown supporting a woman holding a deceased child with his left hand, while extending his right arm to aid a smiling boy.

[6][7] The composition is deeply allegorical: Leopold II, portrayed as a Roman sage, symbolizes the savior of the Maremma (the woman), which has suffered for generations (the dead child).

The smiling boy represents future generations, expressing gratitude to the Grand Duke for his reclamation and land reforms, which vanquished the malaria scourge (the snake).