The tiny little village of Winterborne Monkton, like the other Winterborne villages takes its first name from the river Winterbourne. The second part of its name comes from the Monks of Wast to whom it once belonged. In some ancient records the village is called Winterborne Wast. The manor was once with Bockhampton and a parcel of land in Swanwich (Swanage) called Eight Holes. At the time of Domesday they were held by Ida, the wife of Eustace Earl of Bologne. By 1320 it was held by Stephen Jusseux for his life.

In 1363 by licence of the King, William Payn and Agnes his wife retained the lease of the prior of Wast. It was later granted to Nicholas Tamworth and Joan his wife who conveyed it to trustees who then demised it to Roger Syward in 1369. Joan Tamworth survived her husband and remarried to Gilbert Talbot and they surrendered it to Roger Syward. John Syward, the son and heir of Roger came to the possession of this manor along with lands at Wolveton, Mokleford, Marsh in Sherborne and Trelond in Piddletrenthide.

About 1378 the King pardoned John Syward junior for having acquired the same without licence. When John Syward junior died in 1401 he had held land in Winterborne Monkton, of the Abbot of Bindon, which had been property of William de Wynterborne who was the father of Katherine who was John's mother.

At some point in time after that the manor came into the hands of the Stafford family of Hook and to Edmond Stafford, Bishop of Exeter and was eventually granted to the Dean and Chapter of Exeter.

The parish church of Winterborne Monkton is dedicated to St. Michael and St. Jude. The patronage having once belonged to the prior of Wast and afterwards to the Staffords of Hook then passed to the Strangways of Melbury and the Earls of Ilchester.

Being situated along the route from Dorchester to Weymouth, an old turnpike road established as such in 1761, the parish of Winterborne Monkton once had a turnpike gate. It is recorded that the turnpike gatekeeper in 1841 was Charles Vallis who lived there with his wife Jane, but ten years later in 1851 the gatekeeper and toll collector is Joseph Spracklen aged 49.

On the 1851 census the enumerator recorded that the area covered the two parishes of Winterborne Monkton and Winterborne Herringstone, including Monckton Turnpike. In total there were 87 people occupying 18 houses and 1 uninhabited house.