This research examines the economic impact of climate change adaptation measures on the housing markets of two representative coastal cities in the United States located along the Atlantic Ocean. The results shed light on how adaptation measures and investments influence housing values and local real estate markets with respect to their place-based and local forms of implementation. Numerous quantitative approaches, with the use of geospatial data, panel-data hedonic regressions, and difference-in-differences analyses, are used to examine changes in property values associated with climate adaptation measures and the dynamics of risk perception. The results also signal how risk perception and hurricane characteristics are reflected in housing markets, thereby shedding light on the effects of anticipatory and reactive adaptation strategies on property values in these coastal communities. Collectively, the study suggests which adaptation strategies and characteristics can contribute to maximizing both community resilience and economic benefits against the weather extremes caused by climate change.