Coming from Montaione and following Via Santo Stefano in the direction of Castelfiorentino after about 5 km we meet the hamlet of Santo Stefano.

It appears that the origins of Santo Stefano date back to the Etruscan period in Tuscany, as evidenced by the discovery of many fragments of Etruscan pottery following the excavations carried out in 1995.

In fact, under a farmhouse in the main square of the villa, there are two round cellars dug into tufo resembling Etruscan tombs and two white "marble" Etruscan cipps.

Some documents attest the existence of Santo Stefano already in the 11th century even though there are more reliable news starting from the 14th century, with a documented castle with fortified walls and a territory extended from the Orlo stream in Barbialla to Castelfiorentino.
It was part of the district of San Miniato until 1369 when it was subdued to Florence.

Today, many colonial houses near Santo Stefano have been restructured and converted into villas that are rented out to tourists.