Point Piper Road was the nineteenth-century name for the carriage approach Captain John Piper cut through the bush from the old South Head Road (today’s Oxford Street / Old South Head Road line) toward his Henrietta Villa estate on Eliza Point / Point Piper (grant formalised 1820; house foundations from 1816). The route ran through what is now Woollahra and Paddington along the line later called Jersey Road (renamed 1900 for the Earl of Jersey), then toward Double Bay and the harbour-side roads that became part of the New South Head Road network.
From the 1820s the wider Point Piper Estate passed through Cooper–Levey hands after Piper’s financial collapse; subdivisions and villa traffic kept the road a eastern-suburbs spine under the South Head Roads Trust (from 1848), which also maintained Old and New South Head Roads. Historic Sydney from Old Point Piper Road” views look back from that ridge road toward the town and harbour — caption as road and estate geography, not as an unnamed lookout.
