Abstract: Covid-19 has led to unprecedented changes in functional structures in our cities. Since the mid-20th century, central business districts (CBDs) worldwide have hosted economic and employment activities, leaving suburbia to home the residential function. However, the global Covid-19 responses have resulted in changes in some urban functions, and it is yet to see if these changes would transpire as temporary or permanent. Some argue that the broad macrogeographical pattern of urbanisation is unlikely to be changed. Still, that significant intra-metropolitan, neighbourhood-level and daily life changes are to become part of the new reality. Thus, this article considered these changes by focusing on property trends in the Sydney CBD to reflect on future trends, urban structures, and associated functions. An evaluative single case study desktop analysis was conducted to investigate commercial vacancy rates and rental prices within the CBD of Sydney (Australia) between 2018 and 2021 to reflect on the Covid-19-drive changes and their implications for urban planners. Findings highlighted that before Covid-19, both residential and commercial markets were growing, with rising rental prices and decreasing vacancy rates. However, commercial vacancies in the CBD have increased, and rental prices have decreased since 2020’s lockdown, stressing the dropping demand for commercial spaces. The residential market experienced a different trend with dropping vacancy rates and increasing rental prices. The data analysed provide an initial understanding of how Covid-19 has impacted the Sydney CBD. It poses some insights into potential future trends and changes in the urban landscape. It highlights the implications that the planning profession should consider in the quest to realise sustainable and resilient cities.