Although the Roman road known as Akeman Street passes through Kingswood, not much is known about any Roman activity in the parish, although a late Roman coin was found by chance in the nineteenth century.
Kingswood was part of Bernwood Forest. Bernwood had been a hunting forest from the time of Edward the Confessor. It grew to its largest extent under Henry II. The whole area was not covered by woods; in the medieval period a forest was a place where deer roamed for hunting and so included open land, villages and fields. All those who lived in the forest were not allowed to hunt or even gather wood without a special licence from the king. Bernwood Forest was finally disafforested in the reign of James I in 1635, although it had been shrinking in size since the time of King John (1199-1216). Some medieval pottery from the earlier village was found off Buckingham Street.
Transport was again a feature of Kingswood in the nineteenth century. The Duke of Buckingham built a tramway from the Metropolitan and Great Central Railway as it passed through Brill. Shallow tracks and light cuttings can still be seen. A 19th century privy was donated to the Chiltern Open Air Museum from Mercers Farm in Kingswood.