A First Fleet private marine of the 35th Company, Halfpenny decided in October 1791 to settle in the country. He had married Catherine Wilmot (Lady Juliana-1790), and with their son Joseph, settled on a grant of 60 acres at Norfolk Island. They returned in 1796 and by mid-1800 he was renting a house in Parramatta and by 1804 Halfpenny was shown leasing an allotment at the foot of High Street, where he had built a house. This allotment was the last house on the northern side of the street before the Landing Place. He apparently conducted a business from here trading in grain and may have run an inn on the site, being so close to the barracks and the wharf. He lived opposite to Obadiah Iken.
In March 1809 he held a wine and spirit license in the town and also made a will in September of that year which stated that his house was ‘next to Michael Murphy’s (house)’. Halfpenny died shortly afterwards on 5 September 1809 leaving his property to his wife together with another house in Parramatta and with a property and house at the Hawkesbury. A Gazette Sale Notice described the house as substantial and desirably situated close to the wharf. The house, from James Larra’s auction notice, was advertised as ‘A Commodious House, shingled and weatherboarded consisting of five rooms, well glazed: also a large bullock cart, and cow and calf’. After his father’s death, his son Joseph apparently worked as a seaman on local vessels to help support his mother. Catherine sold her husband’s property and as nothing more is recorded of her, it is assumed that she returned to England to contact the children who had been left behind when she was transported.
 M. Gillen, Founders of Australia; M. Flynn, The Second Fleet; GW Evans, Plan of the Township of Parramatta (1804); E. Higgenbotham, Future of Parramatta’s Past, 1991 item no. 46, pp. 71-2.
 Ibid; Sydney Gazette, 28 Jul 1810, 8 Sep 1810.