The Romans made Holland Park Avenue their main road into London from Silchester and the west, but it probably existed as an ancient British trackway long before that. In Roman times it ran through a densely forested area, part of the huge forest that was later known as the Forest of Middlesex (which according to a 12th century description was full of red and fallow deer, boars and wild bulls).

After the Romans left, the road appears to have deteriorated to such an extent that the then smaller parallel road to the south that is now High Street Kensington took over as the main way into London for travellers from the West of England. But the old road continued to be used by travellers from Oxford and Uxbridge, and until the 19th century it was known as the Uxbridge Road, or sometimes simply the “North Highway”.

From the Middle Ages onwards, the forest was gradually cleared, to be replaced by arable farmland and meadows. Gravel pits began to be worked at what is now Notting Hill Gate, and a straggling village developed along that part of the road at a fairly early stage.

The Holland Park Avenue section of the road remained in open country until the early 1800s. The grounds of Holland House ran right down to the road on the south side. Almost the only buildings were a large house just west of Princedale Road which was the “ handsome pleasant seat” of the owner of the Norland estate; a farm on the site of the Mitre pub, called Notting Hill Farm; and a hostelry called the Plough (a name appropriately indicative of the rural nature of the area) more or less opposite the end of Campden Hill Road (which was then known as Plough Lane).

The road was known for its robbers and footpads. In the 14th century, one Thomas de Holland was robbed of a cart and its goods at “Knottynghull”, and there are a number of other accounts of robberies down to the 18th century. For instance, in 1751, at the level of Holland Park, two gentleman were robbed of their watches and money by men in black masks – 18th century hoodies – “who swore a lot and appeared to be in liquor”. In 1767, it was decided to install lights and appoint watchmen along the Bayswater Road because it was “infested in the Nighte-time with Robbers and other wicked and ill-disposed persons, and Robberies, Outrages and Violences are committed thereon”, but that no doubt that merely caused the robbers to move west to prey on travellers on the unlighted and unwatched section near Holland Park.

The road was often in poor condition, and this was what led to the establishment of the turnpike gate that became known as Notting Hill Gate, so that tolls could be raised from travellers to keep the road in repair. The private Act of Parliament passed in 1714 to authorise the collection of tolls on the road between Uxbridge and Tyburn (Marble Arch) noted that the road “by reason of the many heavy carriages frequently passing, has become very ruinous and many parts are so bad that the same are very dangerous to such persons as have occasion to travel through the road and in the winter season the road is almost impassable for horses, coaches, chariots, carts and other carriages”. Notting Hill Gate was one of several turnpikes subsequently set up on the road from Uxbridge; it was finally removed in the 1860s.

Around the mid-18th century, 170 acres of land to the north of Holland Park Avenue, between Portland Road and Ladbroke Terrace, were acquired by Richard Ladbroke, a member of a rich family of bankers (the land on the south side of Holland Park Avenue belonged to Lord Holland of Holland House). Richard Ladbroke and his descendants did nothing with the land – beyond enjoying its revenues – until 1819, when the estate was inherited by his grandson, James Weller Ladbroke. The latter determined on developing part of the estate to meet the increasing demand for housing within easy reach of London.

It was natural that he should begin with the frontage of the Uxbridge Road, the only real road in the neighbourhood. In 1823 he signed two agreements with developers, one covering the part of the northern side of the road to the west of Notting Hill Farm, and one the part of the road to the east. Under these agreements, the developers undertook to build a certain number of houses. In exchange, once the houses were built, Weller Ladbroke granted the developers 99-year leases of the new houses, which they could then sub-let for income, paying James Weller Ladbroke a rising ground rent, so that both parties were in profit.

In 1824, the first houses were erected on the north side between Ladbroke Terrace and Ladbroke Grove, and in the next 10 years building extended to Clarendon Road, the farm being replaced by an inn. Almost all these houses are still standing.

In the mid 1830s the building boom collapsed as it became clear that the area was still too far west of London to be attractive. All activity on the Ladbroke estate stopped and the houses on the Uxbridge Road, along with a few built at the same time on the other side of the road and at the southern end of Ladbroke Grove and Ladbroke Terrace, remained for the next decade surrounded by countryside. But in the 1840s, demand for housing revived, and over the next three decades the rest of the Ladbroke estate was completed. The few gaps that remained in Holland Park Avenue were filled in. Finally, in 1900, Boyne House made way for the Holland Park Station on the new “Central London Railway”.

As was typical of the period, each separate terrace of houses was given its own name and numbering system. Thus, the houses between Ladbroke Terrace and Ladbroke Grove and the first 12 houses west of the Mitre were part of “Notting Hill Terrace” (and Campden Hill Square, which was built by the same developer around the same time, was called Notting Hill Square); then came Boyne Terrace and Boyne House where the Underground Station now is; and finally between the station and Clarendon Road there was Grove Terrace. It was not until 1895 that this part of the Uxbridge Road was renamed Holland Park Avenue and the present street numbering system introduced.