The name Pennydale began its use in the early part of the 20th Century due to the joining of the name of the prominent family living on the site – the Penny family – and the name "dale" being an old English word meaning "valley". The Penny family – and Edwin Thomas Penny specifically, were so highly regarded in the community that they began calling the area Pennydale as a sign of endearment since the land itself used by the family for fruit and vegetable growing sat in a large valley from Tulip Grove being the highest land in the area, towards the bay. The name became used by family and friends as well as other local residents who moved into the area both during ET Penny's life, but more-so after he had passed away suddenly on 9 December 1916 aged just 67. A newspaper article in the Oakleigh Leader 27 October 1894 page 5 on Penny and his orchards stated about Cheltenham that "the township, by the way, is named after the well known watering place in England, and is sheltered by hills the same as in the old country." This then is the genesis of the Dale section of the name. "(Oakleigh Leader Oct 27 1894 page 5)."