The aging population phenomenon has garnered much attention in recent years, with far reaching implications for the economy, industry and capital markets. This paper focuses on how the aging population affects healthcare REITs in Japan and Singapore by way of a detailed comparative study. Healthcare REITs focus their investments in various medical facilities such as hospitals, medical centers, nursing homes and retirement facilities. Their success is connected to the evolution of the healthcare system and REITs structure. This study focuses on the business model for healthcare REITs, acquisition and distribution implications as well as the stock return performance over time.