This chapter presents a probabilistic approach to assess the long-term economic risk and cost-effectiveness of relevant adaptation measures for Australian housing exposed to non-cyclonic extreme windstorms under a changing climate. The proposed method provides decision-support for the long-term adaptation of residential communities to extreme windstorms and climate change. The cost-benefit analysis suggests that, for all considered climate scenarios, strengthening roof cladding connections is not cost-effective, while improving window resistance or installing window shutters is more cost-effective.