Abstract Background Healthy aging in place is affected by what the neighborhood provides for older adults. The mixed-methods ethnographic study explored the built environmental and contextual effects of urban parks and traditional local coffeeshops (kopitiam) on health practices among older adults in Singapore. Methods A door-to-door survey with 497 older adults from 32 residential blocks in a public housing town assessed exercise and smoking. The walking distances from the residential blocks to the facilities were calculated. Regression analysis examined the associations between the distance and rates of exercise and smoking. Ethnographic assessment data contextualized the quantitative findings. Results Older adults’ exercise was associated with proximity to an urban park but not traditional local coffeeshops. High rates of smoking were clustered in the housing blocks close to the coffeeshops, which provided casual drinking places with smoking tables. The proximity to the coffeeshops was significantly associated with increased smoking and decreased exercise. A walking distance of 200 m to the park and coffeeshops was found to discriminate the outcomes. Conclusions The findings suggested that walking distances of a few blocks influenced health behaviors among older adults. Their smoking habits appeared to be maintained through environmental features and cultural norms attached to the coffeeshops. Policy of urban planning and redevelopment for the aging population needs to consider the socioecology of healthy aging in place.