The physical and financial effects of climate change on housing are simultaneously reshaping financial markets and urban policy and practice. In this roundtable discussion, Savannah Cox interviews five experts working on housing, climate adaptation, and finance in a wide range of urban contexts: Zac Taylor, Isabelle Anguelovski, Alex Fella, Zachary Lamb, and Linda Shi. Participants illuminate how these domains collide in multiple and complex ways in the frontline communities where they do research and capacity-building. Physical climate risks like flooding or heat stress, housing characteristics like tenure, property and land regimes, as well as public and market-led planning and finance approaches collectively shape local housing and adaptation trajectories. This complexity calls for more than simply scaling up the volumes of capital to address housing adaptation finance “gaps” in citie—as commonly advocated for by urban climate policymakers. Even well intentioned and proactive investment approaches can lead to unequal outcomes like climate gentrification. Urban policymakers, financial institutions, civic groups, and other stakeholders must build local capacity to understand and address these dynamics. Climate risk assessment tools, technical support, ownership structures, and other interventions offer potential routes to foster agency and mobilize resources to balance housing and climate goals in cities.