The windmill of Windmill Road, Headington

This detail from a painting of a view of Oxford from Shotover Hill (left) shows the windmill in Windmill Road as it was in 1820.
On the left is the adjoining miller’s house, and at the far right is Highfield Farmhouse, then completely isolated but now in Highfield Avenue. The only other building in this area in 1820 was Titup Hall (now the Crown & Thistle)
There appears to have been a windmill on the same site in Windmill Road from the thirteenth century, but the windmill of the 1820s had only been built recently, as is shown by the following advertisement in Jackson's Oxford Journal of 18 January 1823:

Two years later, it was up for let again: an advertisement appeared in Jackson's Oxford Journal for 14 May 1825 reading: "Headington Windmill. Within One Mile and Half of the City of Oxford. To be sold or let for a term of years,- The above Mill, in full Trade, with a Dwelling House adjoining. For particulars apply to Mr. T. Mallam, Auctioneer, High Street."
Thomas Sharp is listed as both occupier and owner of the House and Mill in Windmill Lane in the Headington Rate Book of 1850. It had a rateable value of £22 10s and a gross estimated rental of £30.0.0.
Richard Lamburn became miller in the mid-1840s, but died at the age of 49 in 1854. John Hunt married Richard Lamburn’s widow Elizabeth just a year after her husband’s death and took over the mill and the four surviving Lamburn children. Between 1856 and 1866 the Hunts had another five children of their own. Hunt is still listed as the miller in the 1871 census, but operations must have ceased soon afterwards, as the 1876 OS map labels the mill "Old Windmill". Directories show that Hunt continued to live privately in the mill house in Windmill Road until 1899, with the census describing him as "Living on own means".
The 1876 OS map (below) shows the windmill still in place at the south-east end of Windmill Road (then called Windmill Lane). To the south-east of the windmill is the pit then known as "Crossroads Quarry" (now Rock Edge), and opposite is the Wingfield Convalescent Home, built for the Radcliffe Infirmary in 1872.

At the time of this 1876 map, Windmill Road was flanked by fields along its entire length, and the most significant change since medieval times was the sudden curtailment of Windmill Lane at the north end by the London Turnpike Road, built around 1790. Before that date, Windmill Lane must have continued without interruption to meet Old Headington village at the Cuckoo Lane field path.
By the time of the 1881 census, the windmill had been pulled down, and four new cottages were built on the site at right-angles to the road, apparently from the stone of the old mill. These, together with the old mill house and two adjoining buildings, were known as Windmill Cottages. Around this time the development of Windmill Lane began, and in a mere 40 years it was transformed from a medieval lane to a suburban street. By 1921, there were fancifully named villas such as Ferndale, Cranford, King’s Wood, Kia-Ora, Lynwood, Druidstone, and Myrtle View. (More sensibly named were Nursery View at 121 and Rose View at 127: these two houses overlooked John Mattock’s rose nursery until it moved to Nuneham Courtenay in the 1960s.)
Windmill Cottages survived until the 1950s, when they were deliberately destroyed by the Fire Brigade during a training exercise, and Windmill House (a children’s short-term reception centre) was built on the site in 1957. Now a hostel for the homeless, it is shown below in 2006. The pavement is noticeably higher than the rest of the road here, with four steps leading up from the road to the kerb.
Headington had another windmill at Bayswater, near the Green Road roundabout where Townsend House now stands, but this ceased operation in about 1800. Bayswater also had a watermill which operated until 1899, and the building still survives.