The COVID-19 pandemic has introduced many new challenges for health, economic activity, and housing around the world. These include the impact on global mobility and multiple prolonged lockdowns restricting internal travel since the pandemic reached Australia in March 2020. However, new travel patterns and changing lifestyle choices have led to very different outcomes for property and rental markets in urban and regional NSW. On the one hand, the loss of international tourism, changing lifestyle preferences, and the resurgence of domestic travel have allegedly stimulated a surge in demand for regional housing at the expense of urban areas. Concurrently, the low interest rate environment operating in Australia’s highly financialised housing market has created huge pressures on Australia’s home-buying market that is affecting all parts of the state. To date, other than lurid media coverage, this shock to local housing markets across Australia has received little scholarly analysis. Therefore, in this paper, we will look to examine the diverging stories of the COVID-19 pandemic inspired impact on Greater Sydney (GSyd) and the Rest of NSW’s (RNSW) rental and home-buyer markets through a multi-scale data analysis approach that triangulates tourist activity, investor sales, and property/rental prices. While scattered evidence from the US, UK and Europe have explored rental and housing markets individually, a direct comparison of the response of commensurate urban and regional housing sectors is lacking. Hence, this study provides the first empirical comparison globally of a local urban and regional housing market to the COVID-19 pandemic.