The city of Bologna has grown and changed over years, from Middle Age through World War Ⅱ up to now. It seems little change in urban landscape but upon closer examination, many changes can be found. Current technology has been applied and merged into the existing buildings in a very natural way. Most of buildings have been remodeled and reused accommodating new functions according to contemporary needs. Thereby the city has sustained its cultural identity, which is the power of urban competitiveness now. Differently from other cases, the city Bologna itself as a whole, is the regenerated city. The purpose of the research is to analyse characteristics of the urban space in terms of culture respect regeneration. The methodology used was walk through observation, along with literature survey and visual recording. Diverse ways of creating new space while preserving were identified.