This house is divided into three small cottages but the vast roof suggests that this building was a late medieval hall-house possibly built in the fifteenth century or even earlier.

This building is one of the oldest in the village and must have been built by someone of some wealth. It may have been this property that was owned by John, son of Thomas Godewyn [Godwin] in the rental of the manor of Glynde of 1462.

The first definitely known owner was John Vynall [Vinall] in 1549. Little is known of Vynall but the house was known as Melwards before 1562, when the property comprised one house and three acres. John Reames, yeoman, owned it before 1652. In 1655 William Simmons, the Glynde blacksmith who had also owned Trevor House, bought this property and in 1679 his son John Simmons sold to Joseph Denham of Glynde, weaver. Denham's widow Mercy married Nathaniel Jeffery in 1702 and they were the owners of this property on the 1717 estate map. In 1722 it passed to Oliver Jeffery, Mercy's adopted son, who sold it to John Kidder, tenant of the Great Farm, in 1739.

Kidder had also bought the plot next door where he built the house now called Hampden House. Kidder's relation John Harris, corn factor, of Middlesex sold all Kidder's property in Glynde and Beddingham to Richard Trevor, owner of the Glynde Estate, in 1759. The house was now divided into "one dwelling with part of the garden and yard; another dwelling with part of the garden and yard; a granary; and the barn which has of late years gone with the Brick House" [now Hampden House]. Rookery Cottages still had a thatched roof until the late nineteenth century, by which time it was divided into three cottages.

The name Rookery Cottages may have first been used in the late 19th or early 20th century. Edward Boys Ellman in his Recollections of a Sussex Parson suggested that the town of Lewes had gained the nickname "the Rookery" from the large number of clergymen who could be seen around the town in their black attire (Lewes Football Club are still nicknamed the Rooks). As Rookery Cottages stand next to Glynde vicarage (now named Hampden House), it is likely the name was given because of its proximity to that building rather than any reference to nesting birds. In South Heighton and Winchelsea there are roads next to their vicarages that include the word Rookery in their name.