Heritage buildings and their surrounding are inseparably intertwined. Anthropological, cultural, symbolic, religious and technical factors are influencing the choice of constructive and architectural features and their interconnection. An important part of heritage buildings, influencing the general outlook, defining its aesthetics, shaping the relationship with the urban context and ultimately contributing to the skyline of the city is the roof. In recent years, numerous timber roof structure assessment methodologies have been developed, which assess the roof structure only by its structural features and state of conservation without taking the link between the roof and the building and its surrounding area into consideration. However, considering the principles of the European guilds, heritage buildings were built with no strict division between symbolic meaning, craftsmanship, architectural aesthetics and urban design methods. This results in a "Gesamtkunstwerk", a total work of art, with harmonically interlinked features and fully connected to its surrounding, leading to a full aesthetic experience. All these features highly influence the aesthetics of the heritage building but also the shape and height of the roof. During the late 19th century and early 20th century, at the dawn of modern architecture and urban design, a bold and aesthetically conscious use of traditional crafts and methods took place in most European cities - the Arts and Crafts movement, Art Nouveau, National Schools. This study aims to define how the relationship between building, roof and the urban context is changing in Timisoara during the late 19th and early 20th century. Ultimately the main scope of the paper is to identify the role of the roof structure in defining heritage structures built around the beginning of the 20th century through a transdisciplinary and interdisciplinary approach.