A watercolour drawing of a view of the Henry VIII Gateway seen from Castle Hill, with houses to the left and the Salisbury Tower behind. In the foreground, a group of three gentlemen are standing on the corner and conversing. Behind, a beggar boy is playing with a dog. On the right, a man is unloading a barrel from a laden horse and cart. Inscribed on the back of the mount in pencil, possibly in the artist's hand, 'Windsor. View of the Town Gate'. The sheet is circumscribed with a black line border, partially trimmed, and mounted on a green and grey wash line border of a type associated with watercolours from the collection of Sir Joseph Banks (for other examples, see RCINs 914546, 914541, 914538).

A pencil drawing of the same view is in the Staatliche Museen Greiz (E 457), as well as a tracing of the subject, probably by Princess Elizabeth (E 453). Paul Sandby and his brother Thomas made many views of Windsor Castle and its surroundings during the later eighteenth century. The Henry VIII Gateway was reconstructed under Henry VIII in around 1511. In 1840 the Salisbury Tower behind was refaced by Edward Blore, and an additional storey added in place of the pitched roof. The houses at the centre of the drawing were demolished in about 1850 during a town improvement scheme.