Political and economic market uncertainties across Europe are affecting the locational patterns of innovative small-medium sized enterprises. Growing numbers of freelancing and locally specific socio-economic dynamics have imposed structural changes in commercial real estate markets stimulating an increasing demand for flexible and shared office spaces. This chapter explores the characteristics of different types of coworking spaces (CSs) in two hugely different cities, Rome and London, from the interconnected perspectives of real estate trends and local market dynamics. In both cases, firms participating in this new geography of innovation, and choosing to occupy a CS, are usually providing services to the local economy, but can often be connected to global networks. Users and locations are directly dependent on these emerging and potentially mutually beneficial socio-spatial urban relationships. The chapter builds upon research in both cities and will consider the development of the CS phenomenon in these two vastly different local economies and real estate markets, drawing on qualitative data from interviews, and secondary market data. Three different typologies of CS are present in both markets: regenerative and socially inclusive spaces, entrepreneurial incubators and commercialised workspaces. The chapter reflects on the development trajectory of CSs in the two cities, evaluating the contrasting experiences of growth to date in each capital city. The research points to two main future trajectories of development: CSs delivered as social infrastructure in partnership with local authorities and private flexible office spaces.