The paper investigates the way social relationships of two different groups of people are reflected in architectural and urban form of buildings. The case study analyses Holesovice, a quarter of Prague, Czech Republic, which is undergoing the process of gentrification. Our research compares spatial characteristics of the new development and original constructions and identifies key differences. The methodology framework is based on the Space Syntax theory and Urban Morphology, supplemented by interviews with inhabitants, developers and city officials. Holesovice is a former industrial suburb of Prague, built mainly in 19th century. The original construction was formed by large regular blocks with private courtyards in the centre. After 1990, when the new economic model entered the Central Europe, many industries were transferred to countries with lower taxes and fewer regulations. Most of the factories and docks were abandoned and therefore offered cheap development sites in exclusive locations, close to the historical city centre and next to the river. The change of economic model together with the “Back-to-city movement” made the areas such as Holesovice attractive for new middle class people, socially strong, often working in international companies. The very character of their work, their engagement in international communities and their strong social position assumes the preference for transpatial relationships over the spatial ones. In the paper we will show how the new developments exhibit different architectural and urban characteristics compared to the original construction. We will argue that the new urban typology and architectural expression reflect the social relations of the gentrified inhabitants. The analysis of the city structure and information provided by interviewing the developers and city officials allow us to understand the change of lifestyle in gentrified quarters and formulate factors leading to these spatial changes.