The Highfield estate in the nineteenth century
In 1875 the Revd William Taylor of the Rookery decided to sell off seventy acres of the outlying land of Highfield Farm for development, and the following advertisement appeared in Jackson's Oxford Journal of 29 May 1875:

It appears that the land did not sell, and on 26 June 1875 there was an advertisement offering the 138 acres of Highfield Farm to be let by tender as farmland from the following Michaelmas.
The following year another try was made to sell the land of Highfield Farm for building, this time on a more modest scale: an advertisement for "two very eligible plots" appeared on 18 November 1976. These two plots were built, and in 1878 the first two houses were built on the Highfield estate: one at the north end (Ellerslie, now Dorset House on the London Road) and one at the south (Highfield Cottage, now 61 Old Road).
The next advertisement to appear in Jackson's Oxford Journal was on 17 March 1877, and this advertised building land on the south side of Old Road on the Highfield Estate. This does not appear to have sold immediately, and may be the land on which Highfield Park was built in the 1880s.
Then continuously, every week for two years from 2 August 1884 to 3 July 1886, there is an advertisement for several lots in plots of ten poles and upwards (average size 35 x 150 feet). These were bought by various builders, and the result was the southern part of Lime Walk, which petered out into a footpath through the Britannia Field, where the coaching inn had kept its horses for a hundred years. The estate developed at the eastern side first because there was nothing but fields to the west, and Lime Walk could be linked to New Headington village via a short piece of road originally called "New Road" but known as All Saints Road after 1910. New Headington village thus initially provided Highfield with all its facilities (the infant school and chapel of ease in Perrin Street, and the shops and Methodist chapel of its High Street).
The Oxford Chronicle for 11 October 1884 (p. 7f) gave the following short report on the development of Lime Walk:
On the Highfield estate, several substantial brick built cottages of a superior order have been erected; principally by the artisan class who own the freeholds.
On 7 June 1890 an advertisement appeared putting out to tender the job of building the roads of New Headington, including Lime Walk. The Ordnance Survey map of 1898 below shows the extent to which the Highfield estate had been developed by that date.

The boundaries of the original old Highfield Farm (marked in red above) were as follows:
- North: London Road
- South: Old Road
- East: The Britannia Field at the north-east, and then the boundary with the houses on the west side of New High Street
- West: The Boundary Brook (now sent underground through the back gardens of the houses on the east side of Valentia Road and to the west of Highfield Avenue).
Highfield Farmhouse is clearly marked on the above map, and the land immediately around it (now occupied by Highfield Avenue) was still being farmed in 1899.
Houses in Highfield by 1898
- London Road (south side): Ellerslie (now Dorset House) dating from 1878 and Brookside (now junior department of Headington School) dating from 1887.
- Old Road (north side) : There was just one medium-sized house in 1899: Highfield Cottage (now 61 Old Road) dating from 1878
- Lime Walk: This was fully made up and named in 1898, with about fifty houses built during the 1880s/1890s. (The Britannia Field belonged to the pub and was not added to the estate until the twentieth century). About half the houses in Lime Walk had their own well or pump (marked W or P on the map), and 23 of the women living there were laundresses or laundry-maids.
- Stapleton Road. This was not yet properly made up or named in 1898 (on deeds of 1893 it is described simply as "New Road"), but the line of the road was marked out and there were four houses on the west side dating from the early 1890s. These are (from north to south) a semi-detached pair (today Nos. 34 and 36), No. 58, and Durhamlea (No. 62). (The latter two each form half of a pair of semis today but were on their own in 1899.) By the time of the 1901 census it appears that the road was still not made up, because the three households listed there are described as being in "(Back) Highfield". These houses were occupied by the families of the farm labourer Henry Higgins, the brewer’s labourer Henry Louch, and the house-painter Arthur White (No. 62). Their respective wives were all laundresses, two of whom worked at home on their own behalf despite the fact their houses had no well or pump to supply water. The name of Stapleton Road is first recorded in St Andrew’s parish register in 1910 but may have been used earlier.
- Latimer Road. This road was already made up and named in 1898, but only had three houses (one detached house incorporating Richard Price’s nursery, and two semi-detached), all on the east side and dating from the 1890s. By the time of the 1901 census there were nine houses listed in this street.
Bickerton Road did not exist in the early twentieth century: it was then just a short spur forming a back entrance to Highfield Cottage on Old Road. The street name first appears in Kelly’s Directory of 1912, when villas called Holmlea, Blairgarry, Celfan, and Brooklea are listed there. The road was named after Joseph Jones Bickerton, a well-known Oxford Town Clerk and Liberal councillor who died in 1894 and who had purchased some of the land of the former Highfield Farm in the Bickerton/Stapleton Road area.
Highfield parish came into existence in 1910. In that year All Saints Church was opened in Lime Walk, replacing All Saints Mission Chapel in Perrin (formerly Church) Street. The name of Highfield (formerly just a western outcrop of New Headington village) was given to the whole new parish, and gradually the focus of New Headington village shifted to Lime Walk.

The above postcard dating from about 1905–1910 shows that the entrance to Stapleton Road was still no more than a lane (its houses in the 1901 census are described as "Back Highfield". This section of Old Road, however, is already much the same as today. The gates of the Highfield Park mansion (now the Park Hospital) are on the left.
See also:
- Malcolm Graham’s case study on the emergence of the Highfield estate in "Housing development on the urban fringe of Oxford, 1850–1914", Oxoniensia LV (1990), pp. 152–156
- Highfield Farmhouse, on whose lands Highfield was built from the 1880s onwards; Highfield's only listed building
- The Britannia, on whose field the top end of Lime Walk was built
- Highfield Park (now the Park Hospital), Highfield's grandest building
- Brookside (now the junior section of Headington School)
- Highfield Cottage (now 61 Old Road), one of Highfield's first two houses
- Dorset House, the other of Highfield's first two houses
- All Saints Church, the building that switched the focus of New Headington village when the parish of Highfield was created
- Eric Hebborn, the famous art forger who grew up in Lime Walk
- Headington Laundresses, who flocked to Lime Walk (13 in 1891; 26 in 1901)
- Postcard of the Lime Walk/All Saints junction, c.1905
- Street numbering in Lime Walk