A Roman road from Dorchester-on-Thames is supposed to run in a north-easterly direction through Chearsley. Roman pottery has been found north-west of the church, and a little metalwork to the west.


Chearsley, or Cheardsley, is supposed to be the site of a battle between Cerdic the Saxon and the Britons but it is difficult to pinpoint the exact location of battlefields of such an early date (e.g. 5th/6th century AD). Some Saxon metalwork has been found north-east of the village, so it was possibly in that direction.


Chearsley is recorded in Domesday and 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).


One or more skeletons were dug up in the 19th century at the crossroads of roads from Chearsley, Cuddington, Chilton and Winchendon, may date from the medieval or post-medieval period, and provide evidence for a gallows. A windmill stood at Green Ash Piece in the medieval period and there were two by the 19th century. Medieval cultivation terraces or lynchets and an enclosure have been identified in field survey north of Chearsley Furze.


Aerial photograph showing Chearsley moat east of St Nicholas' churchThere is a moat near the church that was possibly for the manor house. Between this moat and the River Thame there are earthworks of the medieval village, some house platforms and a possible fishpond and 12th to 13th century pottery has been found here. Other medieval pottery, also dating to the 13th century, was found when one of the bungalows was built on Church Lane in the 1960s, when the school was built and when Regency Cottage on Watts Green was altered. A lot of 12th to 14th century pottery was also found in the front garden of Fairview Cottage and a considerable amount from a public footpath north-west of the church. All this suggests intensive medieval activity at this time.


The oldest surviving medieval building is St Nicholas’ church, which also dates mainly to the 13th century, though it incorporates some 12th century fabric. The tower was built in the 15th century. The base of a 14th century cross stands in the churchyard, possibly a site for preaching. The Rosary also dates back to the medieval period in places, but has been altered and added to over the centuries.


Other listed buildings in Chearsley include Manor Farm, which dates back to the 17th century. Some of the barns at this farm are also listed; a couple are 18th century timber-framed buildings. Sunrise and West End Cottage are 18th century witchert built houses. Witchert is a type of chalky earth peculiar to this area that can is mixed with water and rubble and laid like cob. Chearsley House is a 16th to 17th century timber-framed house. Lower Green Farm dates to the early 17th century and is also made of timber, with a jettied first floor. There are several others of a similar date.


Even later buildings were sometimes abandoned. Earthworks of a few cottages were noticed in Thorpe’s Close/Physic’s Field in the 1980s and at that time some locals remembered there being three terraced houses there within living memory. A cottage on Lower Green Lane, set within a witchert walled garden, was inhabited in 1827 but derelict by 1878. Further down on Lower Green was a 16th to 17th century house that was inhabited up until the end of the Second World War, possibly known as Priests’ Cottage, but it was demolished around 1960. A witchert dovecot on Church Lane was demolished in 1930.


There was a little industry in Chearsley in the 19th century, for instance Short Stone Furlong was the site of a stone quarry recorded on the local Inclosure Act and in deeds. Other quarries are marked on historic maps in the Hill House estate and in Long Hedge Field.