Shifts in property markets are closely tied to changes in investment actors’ relations, shaped by wider economic and regulatory processes. However, the existing literature generally neglects the role of actors’ behaviour and agency within property market shifts, and how market shifts affect cities. In response, we establish a framework that systematically unpacks the role, characteristics and behaviour of property investors in investment market shifts within urban development. We consider market shifts as modifications to established economic and regulatory processes and argue that a multidimensional approach is required to understand property investors and their role within property investment markets that shapes the urban built environment. Our main contribution is a novel approach and methodology to read changing property investor landscapes by linking wider economic and regulatory changes to investment actors and their investment strategies. Empirically, we focus on Amsterdam’s changing investor landscape over the last 15 years. We investigate how crises, represented by far-reaching institutional disruptions of economic and regulatory systems, relate to Amsterdam’s landscape of property investors. Correspondingly, we define three distinct periods of analysis, based on transaction volumes and regulatory interventions at national and local levels: the pre-global financial crisis (GFC) period from 2005 to 2008, the post-GFC recovery period from 2009 to 2013, and the pre-Covid19 boom period from 2014 to 2020. We reveal how Amsterdam’s investor landscape changed over the course of these periods through a mixed methods analysis, including quantitative investment transaction analysis, mapping, and in-depth interviews with investors. We ultimately suggest that reading property market shifts through multidimensional characteristics would enable more targeted policy solutions, moving away from empirically ill-supported stereotypes of property actor behaviours.