Villa Castelli stands on the edge of an escarpment between the Itria valley and the Salento plain, and it has always meant border. The territory is scattered with specchie, the heaps of stones that marked the limits between Messapian and Tarentine lands; and the most studied archaeological site, at Pezza Petrosa, shows well how that line worked: there is a necropolis of more than thirty tombs of the fourth and third centuries before Christ, with decorated pottery, bronze objects and statuettes of Demeter, the goddess of agriculture, and not far off the remains of a settlement with traces of block-built walls. It was probably a Messapian village which, after the conquest by Taranto, became a phrourion, that is a military outpost of the Tarentine defensive system. In the Middle Ages the story repeats itself: the little fortress with its small hamlet found itself on the line between Lombard and Byzantine lands.
The name was formed in layers. From the eleventh century the documents speak of Castellum Caeje, the territory that included Ceglie and much of this area; in the seventeenth century Monte Castelli appears, in the eighteenth «li Castelli», and at last Villa is added, which is not a villa but means village — the full name arrives before the place breaks away from Francavilla Fontana, of which it was a hamlet. The territory then has two things one would not expect: at Monte Fellone horse breeding goes back to the Neolithic, a rare thing in southern Italy and almost unique in Apulia; and in the Antoglia district there is the Fonte Strabone, once called Fonte dei Grani, from which the Canale Reale is born, and which after nearly forty kilometres ends in the sea at the oasis of Torre Guaceto.