The Roman occupation seems to have had no significant impact on the parish of Winfrith: no archaeological evidence has been found to indicate a settled Roman presence. Any community here was probably a group of wooden huts with thatched roofs, housing peasants whose lives were devoted to agriculture. They may rarely have seen a Roman, Winfrith being well off the beaten track as far as communications were concerned.
In the same period Winfrith became the main settlement in Winfrith Hundred, an administrative system used by the Saxons to rule the countryside, administer justice and provide the king with soldiers when necessary. This was perhaps its moment of greatest importance.
Domesday Book in 1086 is the first real evidence of the extent and resources of Winfrith. Unfortunately it is not exact, insofar as Winfrith (written as Winfrode) is combined with Lulworth, Knowlton and ‘Wintreborne’ as one estate, but it still gives a feel of what was here. Winfrith had been held by the king prior to 1066; it was not known how much land to support households was here because no tax was paid by the village in Saxon times. In the four parishes there was land for 24 ploughs, and for the lord’s use there were four ploughs and eight slaves. There were thirty villagers and four mills, together with meadows, pasture and woodland.
Winfrith was unusual among Dorset parishes in having a church mentioned in Domesday Book. The incumbent in 1086 was Bolla (or Bolle) the priest, who also owned one virgate of land and half a plough; all told, this was worth ten shillings. Bolla was also responsible for the churches of Puddletown, Chaldon and Fleet, so he must have been a busy man!