Montecerconi derives its name from the presence once of a monastery of begging friars. There are no traces left of that monastery nowadays.
In 1175 the commune of Montecerconi was property of the Earls Spadalonga and was then suppressed to be annexed to the commune of Asciano.
The hamlet of Torre a Castello derives its name from the castle of the Sienese Republic that was knocked down in 1527. Only the ancient walls have been preserved.
Overlooking the village there's a villa that was property of the Piccolominis, the family of Pope Pio II