This study explores the association of “Sensory Environment” and “Playfulness” with Depression and Cognition (SEPDC) among older adults living in high-density public housing neighborhoods in Singapore. The research conducted cross-sectional surveys with 400 adults aged 55 and above living in 20 such neighborhoods. Path analyses suggest that sensory environment (multi-sensory richness of a place and its capacity to engage) and playfulness (personality trait that enables rendering situations as playful) are associated with reduced depressive symptoms, memory problems, and loneliness in older adults, mediated by the increased “neighborhood cohesion” and sense of “at-homeness.” Hence, sensory environment and playfulness are critical for healthful aging in place and should be considered carefully for better design and planning of aging-friendly housing neighborhoods.