Elderly populations in Asian countries are expected to increase rapidly in the next few decades. Older adults, particularly in high-density cities, spend a considerable amount of time in urban green spaces (UGSs). The World Health Organization noted that UGSs are key to improving the age-friendliness of neighborhoods. Thus, it is necessary to design UGSs for the promotion of healthy ageing to enhance preventive healthcare and relieve medical burdens. This study conducted interviews using a questionnaire with a sample size of 326 participants in the cities of Hong Kong (China) and Tainan (Taiwan region). The inter-relationships among the design of UGSs (e.g., spatial distribution and accessibility, characteristics of plants and UGSs), older adults’ perceptions on safety and aesthetics quality of UGSs, and their self-reported health conditions (assessed by the self-reported SF-12v2 Health Survey) were investigated with bivariate Spearman rank correlation tests. The results indicate that the duration of visits to UGSs was positively associated with mental health and social functioning, two subscales evaluating health-related quality of life in SF 12v2. The statistical model (moderation analysis) showed that such a correlation was especially significant in women and those with low social support and social capital. A positive relationship was found between the physical health subscale and perceived safety in UGSs. This relationship was stronger among older adults living alone (moderation analysis). Furthermore, the color of plants and maintenance condition of UGSs were significant aspects affecting the subjective assessment of aesthetic quality. This study provides useful information regarding how to plan and design urban green spaces with certain characteristics that could improve the accessibility and aesthetic quality, which are preferred by older adults.