This paper examines the late medieval Dubrovnik, exploring its economic and urban development during the 14th, 15th, and 16th century. Through the analysis of key infrastructure projects, legislative regulations, and strategic planning, the aim is to understand how Dubrovnik evolved, adapted, and progressed despite complex geopolitical and economic circumstances. By analyzing the impact of statutes on urban development, this paper highlights how the regulations of the fifth book of Statutes played a crucial role in creating a unique cityscape and enabling the development of sustainable infrastructure. The laws from the statutes show how the people of Dubrovnik engaged in city planning and organization, considering every aspect of its construction and development. The construction of an impressive water supply and sewage system attests to the technical expertise and innovation of the people of Dubrovnik. Through the process of expanding medieval walls and building fortresses, Dubrovnik established its defensive structure that was crucial for protecting the city and maintaining independence. By comprehensively studying the technical, legislative, and strategic elements that shaped the city, the paper emphasizes historical continuity and the resilience of Dubrovnik's architecture, urban planning, and economic structures, highlighting how they have preserved their fundamental function despite changes over the centuries.