Cities are currently undergoing vast changes, which have very significant implications for the functioning of the housing market. In particular, it should be stated that the traditional residential market, in imitation of the smart city concept, is becoming increasingly smarter. This smartness can be expressed in four dimensions: the “automatic” rental housing market; innovative digital platforms in the traditional housing market; innovative policies and housing models; and the ability to forecast demand on the housing market, which together form the so-called smart housing concept. On this basis, this study attempted to assess empirically the smartness of the residential markets in Polish provincial capitals. Firstly, after a thorough analysis of digital housing portals, official websites of Polish provincial capitals and public statistics data, the smart housing concept was operationalised in all its dimensions by defining appropriate indicators measuring its level in a given city. Then, using the zero unitarization and entropy weight methods, followed by a no-pattern synthetic measure, a comprehensive smart housing index was obtained for each city investigated. Research results showed that there is a large degree of variation in the level of smartness of the housing markets in the examined cities. Furthermore, the analysis also indicates that the economic dimension of the smart city concept and the co-working concept are the main driving forces behind the development of smart residential markets. In addition, the study reveals that the implementation of the smart housing concept has a positive impact on the quality of life of city inhabitants.