A road forming the eastern boundary of Greenwich Park since the enclosure of the common in the fifteenth century and probably a cart track from the river to Blackheath for many years before. Despite evidence that the road once led to a turf maze in Blackheath, the name appears to come from 17th century resident Sir Algernon May. Gravel extraction dominated the east side until around 1650. After the workings had been exhausted the land was let to smallholders, who were gradually eased out to make way for the homes of gentlemen, scholars and naval officers. In the first half of the twentieth century many of the houses were subdivided and some were destroyed in the blitz. The elaborate Maze Hill House was demolished in 1932 for an estate of smaller properties.

At the junction of Maze Hill and Westcombe Park Road are the brooding towers of Vanbrugh Castle, built around 1720 by the great dramatist and architect Sir John Vanbrugh, who also designed Castle Howard and Blenheim Palace. Vanbrugh created a fortress-like complex of mock-medieval buildings, but only the centrepiece survived a spate of redevelopment in the 1890s and 1900s that followed the opening of Maze Hill station in 1876. The Blackheath Preservation Trust bought the site in 1976, restoring the castle and converting it into four dwellings. The northern part of the locality is now dominated by modern municipal housing, including 1960s tower blocks.

Vanbrugh Castle, seen from Greenwich Park

Former slave Olaudah Equiano lived briefly at 111 Maze Hill. A pioneering abolitionist campaigner, he published his autobiography in 1789. The book was one of the first personal accounts of slavery and became an international bestseller.