This chapter discusses the social and symbolic significance of the current process of conversion of centrally-located industrial heritage complexes in Tallinn. It argues that the process of conversion is an effect as well as an engine of urban cultural change, reflected in differentiating economic and socio-cultural practices in salient visibility of physical and functional change in the city. Historical industrial buildings and whole areas in city centres present a cultural asset, an appealing heritage to individuals, property developers, entrepreneurs and politicians to be transformed into status, profit or benefit of a city in a broader sense. The sites of conversion in focus in the chapter are on the urban scene of the city of Tallinn since 2006 with pioneering Fahle Maja/Fahle House, closely followed by first buildings in Rotermanni Kvartal/Rotermann Quarter 2007 and Lutheri Kvartal/Luther Quarter in 2008. Residing in a historical building means encountering certain aesthetic canons which might be eradicated or cherished by distinct understanding of authenticity.