Field-walking surveys east of Cowley Farm have recovered lots of prehistoric remains in Cuddington, such as Neolithic to Bronze Age flint cores, blades, flakes and scrapers and Mesolithic microliths. Icthyosaur remains were also found, dating to well before humans were around. Some evaluation trial trenching in the same area recovered some prehistoric pottery and flint from later features. A Roman ditch and possible building with associated pottery and tile were identified in the same investigation. An enclosure was seen on an aerial photograph of land east of Lowergreen Farm, but the date is unknown.


Cuddington was part of Haddenham manor and parish in the medieval period and seems to have remained so until around the middle of the sixteenth century. There are no positively medieval earthworks to attest to a larger village at that period but many of the houses seem to have medieval cores, such as Green View and The Pitchings. The church was first built in the thirteenth century and has a fourteenth century north aisle and porch with a fifteenth century tower and nineteenth century restoration.


Many of the other buildings date to the sixteenth, seventeenth or eighteenth centuries and are either made of witchert or timber, such as Spicketts, Beam Cottage or Bridgeway. Other remains from this period include historic records of two watermills and a fishery, possibly at Evershipp Water. There are records that the Baptist Chapel existed by the seventeenth century but the present building is nineteenth century, with its associated cemetery. The parish pump on the green also dates to the nineteenth century and there sees to have been a windmill south of the watermill on a nineteenth century map. There is also a rare survival of a telephone kiosk, the design of which dates to 1935.