A street is a key element of urban space for spatial connectivity and social activities. Throughout history, streets have adapted to local characteristics, but over time, street image has increasingly been influenced by technical criteria. This paper explores the historical development of streets, their components, and the design factors that shape the image of the street. Additionally, it discusses and elaborates on the different street patterns in the city based on their purpose. The city of Osijek was founded on an elevated area along the Drava River, its strategic position throughout history attracted many conquerors. From the Roman settlement of Mursa, the city developed into a significant medieval and Ottoman center. Over the centuries, it underwent numerous transformations, including Ottoman occupation and modernization in the 18th and 19th centuries. Strossmayer Street, which followed this development, is today one of the city’s key streets, important for traffic and urban life in Osijek. The analysis of the morphological structure of Strossmayer Street encompasses various features, from the positioning of houses in relation to the street to the building age and roof shapes. The General Urban Plan (hereafter referred to as GUP) for the selected part of Strossmayer Street prescribes regulations for the positioning of buildings and the minimum number of building floors. Furthermore, the analysis of this part of the street elaborates on the use and purpose of the land, forms of use, and construction methods. The study concludes with the processing of collected data on floor area ratio (FAR) and floor space ratio (FSR), as well as the number of building floors. Finally, a three-phase plan is proposed to improve the current state of the analyzed part of Strossmayer Street. This paper aims to present the recorded and available changes in the morphological structure of Osijek’s streets, using the analyzed part of Strossmayer Street.