Greenoaks Avenue is short, steep, and addresses exactly the class of buildings the peninsula keeps most carefully. It runs from Darling Point Road down toward the harbour, its length defined by the walled grounds of Bishopscourt, and in the early 1930s it was the Sydney address of Sir Charles Kingsford Smith.

The avenue takes its name from Greenoaks, the mid-nineteenth-century estate of the industrialist Thomas Sutcliffe Mort — the house that has been known, for the past century and more, as Bishopscourt. The avenue was cut to give access to the Greenoaks property and to the smaller villa allotments subdivided around it, and the shape of the street has essentially not changed since that nineteenth-century layout.

What stands on it

The northern side of the avenue is substantially taken up by the walled grounds of Bishopscourt at number 11A — the Gothic Revival residence first developed by Mort from 1846, enlarged by Hilly, added to by Edmund Blacket in 1859, and further extended by Leslie Wilkinson in 1935. It was the home of eight successive Anglican Archbishops between 1911 and 2015, and returned to private hands in late 2015. The southern side of the avenue carries a sequence of smaller Edwardian and interwar houses and a small number of post-war apartment blocks, in a pattern characteristic of the peninsula's interior streets.

The aviator on the avenue

In the early 1930s, Sir Charles Kingsford Smith — then the most internationally famous Australian of his generation, two or three years after his 1928 first crossing of the Pacific — kept a house on Greenoaks Avenue. The residence is attested in contemporary sources, though the specific street number has not been reliably documented and is not inscribed on the building today. Kingsford Smith disappeared over the Andaman Sea in November 1935, and the house passed out of his family's hands shortly after.

The peninsula has, characteristically, declined to memorialise the connection. The avenue retains a plaque on the Bishopscourt gates acknowledging the Anglican tenure; it carries no sign that it was, for a short and consequential period, an aviator's address.