Sandby painted many views of Windsor, where his brother was employed as draughtsman to the Duke of Cumberland, Ranger of the Great Windsor Park. Sandby's career shows how skills in painting landscape could develop from the mapping and plotting of the land required for military purposes: in 1747 he was appointed draughtsman to the Military Survey in Scotland.
The simple horizontal format and bird's eye view point in this work show Sandby's links with the topographical engravings of the previous century.
The view is from the Duke of Roxborough's Estate looking south. The Duke of Roxborough bought the Remenham Estate (later called Beaumont) for his eldest son, later the Marquess of Bowmont, in 1751; he sold it in 1764 to Prince Henry, later the Duke of Cumberland. 'Old Windsor' must therefore date from between 1751-1764. If 'Old Windsor' was painted for Sir Joseph Banks (1743-1820) it can be dated more precisely to around 1760.