Windward Avenue was an unnamed dirt track with a handful of houses until the early to mid 1950s. When the decision was made by Council to seal the road and give it a name, Nance Meyers as the oldest resident was invited to name it. She chose the name Windward Avenue, mistakenly believing it meant sheltered from the wind (whereas, of course, it means the opposite). Nance was the wife of Norman Ernest Meyers who founded Mynor Cordials. Mynor’s factory was located in Macpherson Street, where McIntosh Motors is today. Nance Meyers lived at 3 Windward Avenue for almost 60 years and died in 1998 at the age of 92.
In about 1958 Brian and Jacqueline Dwyer bought a steep irregular terrain, no. 12, on the high southern side, land on which only modern architects and builders would dare build. The cost of the land was less than two thousand pounds. The pioneer Modernist architect Sydney Ancher, and Sabemo the builders undertook this work which was completed in 1960. This photo was taken during the construction of the house.
The architect John Gibbins built on no. 16 shortly afterwards, followed by Len and Dorothy Crawford on no. 9. Dorothy Crawford was a member of Mosman Council for many years.
In later years the road was sealed and extended to meet Amaroo Crescent further downhill, and more blocks of land came up for sale. A number of project houses were erected by Pettit & Sevitt who used modular designs by Ken Woolley and other esteemed architects.