The common border between Bulgaria and North Macedonia, alongside the regulatory requirements stemming from Bulgaria’s membership in the European Union, provide grounds for comparing the legislative environment in both countries. This article presents a comparative case study of the regulatory frameworks governing community pharmacies in Bulgaria and North Macedonia. The aim of this study is to examine the specific features of current legislation related to the operation of community pharmacies, and to identify similarities, differences, and gaps in the organizational structure of pharmacy services, the population’s access to pharmaceutical care, and the qualification requirements for personnel working in community pharmacies. Bulgaria has been a member of the European Union since 2007, while the Republic of North Macedonia has had official EU candidate status since 2005. This provides a basis for comparing the regulatory frameworks of an EU and a non-EU system within the same regional context. In both countries, the overall pharmacy-to-population ratio exceeds the European average (3.3 pharmacies per 10,000 inhabitants), indicating sufficient availability. However, pharmacies are predominantly concentrated in major urban areas. In Bulgaria, challenges remain in ensuring access to pharmaceutical services in smaller and rural settlements, while in North Macedonia, the provision of such services is better ensured. The findings of this case study may be particularly relevant for countries undergoing health system reforms or EU harmonization processes.

National legislative frameworks governing prescribing, pricing, reimbursement, and dispensing play a decisive role in shaping access to medicines. This study examines the financial availability of medicines in Bulgaria and North Macedonia through a comparative review of national pharmaceutical legislation, pricing mechanisms, reimbursement models, and digitalisation policies, assessed in relation to European Union standards. The findings indicate that access to medicines in both countries is shaped by the combined effects of multiple regulatory and financial instruments rather than by individual policy measures. Both systems apply strict control of prescribing and dispensing, external reference pricing, and positive reimbursement lists, reflecting alignment with international recommendations. However, significant differences in policy design lead to divergent access outcomes. Bulgaria’s more advanced digitalisation of prescribing and reimbursement, including mandatory electronic prescribing for selected therapeutic groups, enhances regulatory oversight and expenditure control but is associated with higher patient out-of-pocket expenditure, partly due to the application of the standard value-added tax on medicines. In contrast, North Macedonia combines lower taxation with capped patient co-payments, higher regulated pharmacy margins, and fixed pharmacy remuneration per prescription, contributing to improved financial affordability for patients while supporting pharmacy sustainability. Additional instruments, such as the Generics without Co-Payment List, further strengthen patient financial protection. The study provides comparative evidence relevant to pharmaceutical policy reforms and highlights the importance of balanced regulatory approaches that promote affordability, system sustainability, and equitable access to medicines.