The urban development of the walled city of Nicosia following the 1974 division of Cyprus has reinforced the impact of the current political situation on the protection and management of the historic core of the city. The bi-communal Nicosia Master Plan is a considerable step in decelerating the loss of the city’s heritage, but highlights issues rooted in its ongoing political and physical division. Furthermore, the limited bi-communal engagement between the Greek Cypriot (GC) and Turkish Cypriot (TC) Municipalities of Nicosia impedes the sustainable protection of the city’s historic urban core. This outcome advocates a stronger understanding of its strengths, weaknesses, opportunities, and threats in order to effectively address the eminent loss and decay triggered by the existence of the UN buffer zone currently dissecting the city between the North (Turkish Cypriot Government) and South (Greek Cypriot Government). Methodology: This research employs a single embedded case study approach. The research methodology is qualitative and based on a triangulation of literature findings, empirical research, and semi-structured interviews. These have informed the SWΟT analysis, discussion and conclusions that follow. Findings: Despite the bi-communal Nicosia Master Plan’s contribution in safeguarding Nicosia’s historic urban core, the findings demonstrate a departure from its wider, collaborative heritage regeneration trajectory and highlight the detrimental impact of the buffer zone on its adjacent areas. It has also established that buildings closer to the boundary suffer the most, despite specific measures to attract interest and investment in the area. Originality/Value: The heritage management of walled Nicosia on both sides of the divide is an ongoing, sensitive topic which remains largely unexplored, particularly from an empirical perspective. As a result, this research furthers the currently restricted academic discussion about walled Nicosia’s heritage by introducing new topics linked to its division and heritage management. In doing so, the creation and dis-semination of new knowledge on the city is achieved, subsequently promoting a more informed heritage protection on both sides of the Cypriot divide. Furthermore, through the applicability and generalizability of the research findings, this research informs the approach for heritage protection of other contested urban environments internationally.