This paper follows a call for a ‘long view’ perspective on contemporary housing problems and policy. It applies this longitudinal lens to a multi-city comparative ethnographical study that investigates and relates place-specific and common trajectories and policies in regard to contemporary urban housing. By comparing Auckland, Singapore and Berlin from a heterodox political economy perspective, it demonstrates how contemporary challenges and proposed solutions over housing have deep-seated historical and geographical roots that are usually overlooked. It suggests that comprehending current housing issues as cumulative effects of developments and policy (non)-action taken in the past, and relating and evaluating those constitutive trajectories and transformations across (disparate) cities, current academic and policy debates can be enriched and deepened. One lesson is that ‘learning from the past’ may be a more promising crisis response than nowadays’ politically fetishised learning via global best practice and spatially mobilised policy.