<p>Greening is a critical method to benefit well-being, emotion, stress, and preference. Urban heritage greenery has the potential to offer emotional and recreational benefits, attracting and satisfying tourists. However, few studies, particularly quantitative studies, have supported the benefits of greenery at heritage sites. The primary purpose of this study was to examine the benefits of urban heritage greenery. This study hypothesized that urban heritage greenery positively affects recreational benefits, long-term value, well-being, positive emotion, negative emotion reduction, perceived stress reduction, attention restoration, landscape preference, place attachment, destination image, perceived quality, satisfaction, and behavioral intention. The study was divided into two parts: Study 1 explored the experiential benefits of urban heritage greenery in heritage tourism, while Study 2 concentrated on the visual benefits of urban heritage greenery through a pure visual assessment. The results of the two studies showed that heritage greenery positively affected psychological variables, including higher recreational benefits, long-term values, well-being, positive emotion, landscape preference, attention restoration, place attachment, perceived quality, satisfaction, and behavioral intention. Urban heritage greenery can effectively enhance these benefits, owing to its medium-to-high explanatory power. Conversely, low levels of urban heritage greenery can reduce these benefits and lead to problems with heritage management and maintenance. Heritage greenery is a key driver of enhanced visitor experiences and psychological benefits and a crucial element for heritage management. The applicability of this study is mainly limited to Taiwan and non-World Heritage sites, as World Heritage sites were not included.</p>