Older adults’ out-of-home behaviors (OOHBs) are critical for maintaining health and quality of life. Taking Singapore’s Yuhua East as a case, this study applied a qualitative approach to explore what neighborhood environmental factors influence older adults’ OOHBs. Twelve older adults were recruited for walk-along interviews through the use of purposeful convenience sampling. A content analysis was conducted using NVivo 11 via an inductive approach. Research results revealed 12 categories of environmental factors that affected older adults’ OOHBs: access to facilities (shops and services, public transit, and connectivity), pedestrian infrastructure (sidewalk quality, sheltered walkways, universal design, crossings, benches, and public toilets), aesthetics (natural elements, buildings, noise, and cleanliness), traffic safety (behavior of other road users and road width), safety from crime, wayfinding, familiarity (long-term residency and routine activities), weather, social contact, high-rise, high-density (lifts, population density, flat size, and privacy), affordability (shops and services, as well as transportation), and maintenance and upgrading. This analysis concluded that access to facilities and pedestrian infrastructure are important for older adults’ OOHBs. Considering Singapore’s weather, sheltered walkways, the proximity of facilities and connectivity should be given serious emphasis. In addition to physical factors, social contacts and the affordability of shops and services are also important.