[2] The village was anciently known as Lanmihangel y Twyn (the Llan of Saint Michael on the hillock), following the Norman invasion of Wales this name was commonly transliterated into Michaelston Le Mont.

[3] Robert Fitzhamon gifted both the castle and the "Lordship of St George" to Sir John le Fleming, whose family maintained possession for generations.

It continued in his descendants until, on failure of issue male, William Fleming sold the estate to Lewis Thomas of Bettws;[6] while an alternate account states that the le Fleming line ended in an heiress, who married a Thomas, of Llanfihangel, through whom a sale of the property was made to the Wyndhams of Dunraven.

A Topographical Dictionary of The Dominion of Wales (1811) by Nicholas Carlisle described Flemingston as belonging to what is now called the Hundred of Cowbridge, within the County of Glamorgan.

The John Marius Wilson's Imperial Gazetteer of England and Wales (1870–72) states that the Flemingston parish was within the Bridgend district or Glamorgan.

Flemingston was described as being one estate, the manor belonging to Sir John Fleming, one of the twelve knights who came in with Fitzhamon in the time of William Rufus.

The church contains a monumental stone slab bearing a full-length effigy of a lady, probably dating from the 14th century.

[7] Flemingston Court dates to the first half of the 16th century and possibly functioned as a rectory or steward or farm manager's house.

[9] Rose Cottage is dated to the 16th or 17th century, built from rubble stone, with a thatched roof and "eyebrow windows".