There had been an earlier attempt to erect a pair of cottages on part of this site by Mr W Hayter in 1906. However, the site was always owned by the Glynde Estate, suggesting that Hayter was hoping to obtain a lease on the land. For whatever reason, Hayter's cottages were never built and on 14 May 1920 East Sussex County Council submitted a building regulation application on for a pair of semi-detached cottages. These were to house the village policeman in the southern cottage and a council road worker in the northern cottage.

The site had been purchased from H R Brand, then owner of the Glynde Estate, for £50. It comprised 2 roods of land in Beddingham on the west side of the road from Glynde Station to Little Dene Crossways.

The builders were Godfrey Brothers of Seaford who completed the houses in May 1921. A County Council tenancy register survives and shows that the roadman's cottage cost £1069 to build and was first occupied on 25 July 1921 by David Holloway, who paid 10 shillings a week rent. David Holloway died in September 1945 and the tenancy was taken over by his son, F R Holloway, a labourer, on 24 September 1945. He was still the tenant in 1963, paying a weekly rent of 33s 6d. F R Holloway was one of twins who both worked for the County Council and both lived at the house with their mother. The twins purchased the house from the County Council in the 1980s.

No list of tenants survives for the police house but, presumably, up to 1963 it would have been occupied by the village policeman, the first occupant moving in on 1 July 1921. The village policeman had previously lived at 2 Malthouse Cottages, Glynde. In 1966 Downland became the residence of the local District Nurse, who had previously lived at Little Talland, Firle.

Ray Foord, who had owned the local milkround and lived at Glyndebourne Farm Cottage, bought Downland from the County Council when he retired in the 1980s.