In 280 a.C. the Roman army spreads in Etruria and in this period there is a real reorganization of agriculture through the formation of large farms that have the task of producing for a national market. The remains of some of these villas can still be admired in Settefinestre, San Sisto, Civitella and Maliguardo.
The Roman invasion prepares the advent of a civilization that bases its roots on the possession of the land and in the force of arms. So from the Roman villa we slowly move to the small rural agglomerates that will tighten more and more around the castles to defend themselves from the barbarian incursions and protect their cultural identity.
During the Middle Ages, the Aldobrandesca County reigns in Maremma. These, in the IX century, get the territory that now corresponds to the province of Grosseto as a fief and place their headquarters in Roselle. The Saracen raids take the population away from the plains to take refuge on the hills, on which there are many fortilizi like Marsiliana, Manciano, Scansano, Pereta and Magliano, which constitute the most immediate line of defense near the valleys crossed by the Ombrone and Albegna rivers.
With time, the landscape changes again and small towns are formed everywhere with houses leaning against each other and up the castle.
The abandonment of the countryside favors the spread of the marshes and malaria that torment the Maremma for the whole 800. The lands of which the Etruscans boasted give way to pasturage or even to the swamps and agriculture is becoming increasingly impoverished.
The Aldobrandeschi, faced with this degradation, are forced to move their headquarters elsewhere and move to Sovana and Santa Fiora.
The Castle of Scansano was born around the year one thousand and thanks to its position it constitutes a terrible fortress. The inhabited center extends rapidly, occupying the southern part where the Church and the Praetorian palace stand. To the north, towards the entrance door, the craft shops and warehouses for the conservation of foodstuffs are developed.
At the beginning of the 1300s, Senesi subjugated Grosseto and began to dismantle all the Aldobrandeschi castles, ordering the destruction of the castle of Scansano and its walls.
In 1439 Scansano, together with Poggioferro and Murci, became part of the County of S.Fiora which in the meantime passed under the dominion of the Sforza family.
The constitution of the free commune confers a completely new face to the districts. The castles are abandoned and the populations gather in the villages and begin the tilling of the lands that the feudal lords had abandoned. In the inhabited areas there are artisan shops and the economy begins to rise. The first vineyards and olive groves are born in the hills, the old paths become more comfortable roads and in the countryside life is organized in agricultural communities.
The XIX brings to Scansano a great economic awakening thanks to numerous wealthy and expert families in the agricultural sector, for which, in this period, the first farmhouses linked to the half-diary relationship are born.
In 1897, the annual summer transfer of the most important public offices in Grosseto ended, a history that has gone down in history as the period of the Estatatura, during which the rich families of Grosseto moved to Scansano to escape malaria.
During the various events the town of Scansano is enriched by many public buildings such as the Palazzo Pretorio, the Palazzo delle Podestà, the Communications Treasury, the Monte dell’Abbondanza and the Casa dello Spedale.
The paths that linked Scansano to the rest of the territory were the Salaioli road (so called because it passed through the salt trade), the Marina road coming from Talamone and the Collacchie road. Except for the Salaioli road, which arrived just in front of the Scansano gate, the others joined the Olmi, the most evocative part of Scansano. Here in ancient times there arose a small church called Madonna degli Olmi that welcomed the traveler passing through these lands.
The healthy air and the suggestiveness of the place attracted many noble families who, in addition to cultivating the countryside, built many elegant buildings with portals in pietra serena on which they engraved their noble coats of arms.
The urban development of Scansano can be summarized as follows: from the 1200s to the 1500s, the historic center is formed, which will be defined by the inhabitants themselves as “Il Dentro”, due to the fact that it is enclosed within the old walls. From 1600 to 1800 “Il Borgo” was born.
The oldest part of Scansano is, in fact, “Il Dentro”. This is gathered around the nucleus of the “Court” in which the Castle once stood. Starting from the sixteenth century Porta dell’Orologio overlooking Piazza Garibaldi, the ancient town runs along Via Vittorio Emanuele II to the Church of S. Giovanni Battista.