Its locality is mostly situated on a 200-acre lot initially purchased from the Crown in 1837 by William Henry Roberts, a Sydney-born son of convict parents.

His life is a fascinating story. At age 14, he was left a substantial inheritance on the death in 1819 of his father, a Sydney publican. As the eldest son, William helped his mother manage their hotel, the King’s Arms Inn in Sydney, and also their numerous land holdings. In 1822, William proceeded with cattle and servants through the Cow Pastures to a farm near the ‘Wingay Carraby River’, which his mother had purchased.

Young William developed a shrewd business sense. He did well from cattle dealing and butchering and later owned several Sydney hotels. He was a close friend and business partner of Andrew Badgery, whose sister Ann became William’s wife in 1823.  

In 1837 William purchased Lot 75 from the Government, being 200 acres at Mittagong on the Great South Road. He sold it in 1840, not long before his death in August 1841 at age 35. His widow was left to raise their five children.

It was Lot 75 which would eventually become Willow Vale village in 1882. Up until then it passed through a succession of speculative owners, some of whom were wealthy and others who had to sell quickly, due to the boom and bust economy. There is no evidence that any occupied the land.

They all, however, realised the land’s potential. By 1837 inns had been established by settlers to cater for travellers in the vicinity north of Mittagong on the Great Southern Road, renamed Hume Highway in 1928. The area was a camping ground for those droving cattle who, having completed the ascent from Bargo, would rest their herds overnight. The road was used as well by travellers, settlers and squatters to access the southern counties and squatting districts.

Lot 75 was divided into two lots, 150 and 50 acres, in 1841. These had numerous owners until 1858 when both were purchased by James Reilly and three Tooth brothers, maltsters and brewers, all of Sydney, who also purchased an adjoining 73 acres.

In 1859 the land was sold to Thomas Holt. He had moved to Sydney from England in 1842, becoming a wool buyer, financier, company director and pastoralist. He served on the NSW Legislative Assembly and Council, taking an active role until 1881. He took a great interest in education, personally donating land for school sites.

Construction of the Great Southern Railway from Picton to Mittagong was underway at the time of Holt’s purchase and its route through his land necessitated the division of his lot into two parcels, the smaller being east of the rail line across to the main road, with the larger block to the west.

The completion of the railway in 1867 was the impetus for growth in the locality. One who realised the potential was Bartholomew Rush, owner of a nearby boarding house. In 1865 he purchased 200 acres to the north of Holt’s land where he had a railway platform built, known as Rush’s Platform.

Holt sold his land in 1872. After a rapid succession of owners it was purchased by John Wilson, merchant, and William Binsted, surveyor, both of Sydney.

They subdivided the 200 acres and offered it for sale in 1882. The private village of Willow Vale came into being.