Chepstow Villas is a pleasant leafy street that runs between Pembridge Villas and Kensington Park Road. It is intersected by Ledbury Road/Chepstow Crescent; Denbury Road/Pembridge Crescent; and Portobello Road.

Until the 1840s, the whole area was agricultural land. But in around 1840 the demand for housing began to increase and the second great surge of housebuilding began on the Ladbroke estate. The Ladbroke family, the owners of the estate, had begun to sell off parcels of land to speculators. James Weller Ladbroke retained the eastern part of what is now Chepstow Villas (numbers 1-15 odds and 2-32 evens), but the central part, up as far as Portobello Road, passed into the ownership of Robert Hall of Old Bond Street. And after James Weller Ladbroke’s death in 1847, his heir Felix Ladbroke sold the western plot to a speculating parson from Bedfordshire, the Rev. Brooke Edward Bridges, and the latter then sold it on to another developer, Thomas Pocock. So there were a number of different landowners involved in the development of Chepstow Villas.

During the second half of the 1840s and the early 1850s, the street was laid out and development proceeded apace on all three parts of Chepstow Villas, as well as in neighbouring streets. The landowners signed agreements with a number of developers, who each undertook to build a certain number of houses. Many of the developers were professional builders, but there were also gentlemen and tradesmen interested in property speculation who then employed their own builders. Once the houses were built, the landowner would give 99-year leases of the houses to the developer in exchange for an annual ground rent. The developer would then sublet the individual houses in order to recover his investment. There are records of the dates on which the individual leases were granted, and from these one can work out when the houses were built. Although the landowners exercised some control over what houses were built, much was left to the individual developers, which explains the variety of styles to be found in the street.

One of the main developers, with whom both James Weller Ladbroke and Robert Hall signed agreements, was a civil engineer called William Henry Jenkins who hailed from Herefordshire on the Welsh borders. It was he who appears to decided the names for the new streets, choosing the names of places near his home – Chepstow, Denbigh, Ledbury and Pembridge.

The road started to decline around the turn of the twentieth century.

During the Blitz in the autumn of 1940, a number of bombs fell on Chepstow Villas, mostly causing only minor damage to roads and gardens. But an incendiary bomb on 15 October 1940 damaged the top floor of No. 46; and on 8 December 1940 Nos. 19 and 20 were damaged and two people had to be evacuated, according to air wardens’ reports.

In the 1960s and 1970s, Chepstow Villas began a steady ascent to renewed fashionability. An early sign came in the mid-1960s, when the Conservative MP Julian Critchley (1930-2000) moved into the detached villa at No. 50. He was shortly joined by his friend and fellow politician Michael Heseltine, who kept the house until the mid 1970s. By that time the street had become quite sought after, and Heseltine sold the house to a Saudi princess. She did not move in immediately, and the house (by then valued at some £200,000) became the subject of a famous squatting case. A group of squatters called “Mustard” or Multiracial union of Squatters to alleviate Racial Discrimination” moved into the house, announcing that they proposed to stay there until the owner was ready to move in. The Saudi princess finally obtained an eviction order in 1976.