This article considers how futures thinking might be applied to the problem of housing affordability. The problem and possible paths to solutions are explored, with a particular focus on the area of policy. Sohail Inayatullah’s Six Pillars of Futures Thinking is used as a methodological and analytical framework focusing on the Town of Whitchurch-Stouffville as a case study. The article concludes with a discussion highlighting areas for consideration and possible action, specific to Whitchurch-Stouffville.