The redesign of Eleftheria Square was imagined to be the spearhead of a new era in Nicosia’s urban identity. However, the capital of Cyprus is still struggling with a complex decision-making process and a weak planning system. Rapid urban change, coupled with urban sprawl, are raising questions about the future of Nicosia, and other Cypriot cities. The aim of this paper is to position the redesign of Eleftheria Square within Nicosia’s urban historical context. The paper explores the Ottoman and British approachesto the city’s development, exposing how their legacies manifest in current ideologies and values about urban space. The redesign of Eleftheria Square is presented as an example of a third ‘glocalised’ approach, exacerbating the existing dichotomy between the Ottoman and British approaches. The article concludes by questioning Eleftheria Square’s legacy and advocating for a wider discussion about what constitutes, influences and drives urban change in Nicosia.