Visible greenery plays an important role in improving the visual appeal and liveability of urban streets. Planting street trees is one of the most effective ways to increase residents’ daily perception of urban greenery. However, previous studies have often treated visible greenery as a static condition, failing to capture how its visual benefits evolve with tree growth, species differences, and variations in street spatial form. This study adopts a simulation approach to quantitatively assess the dynamics of visible greenery provision (VGP) in urban streets. Two typical street types and two common urban tree species in Munich were selected, with tree crown geometries derived from municipal tree inventory data. A total of 280 planting scenarios were simulated to explore how tree species, planting density, and street type jointly influence VGP over time. The results indicate that street type has a significant impact on VGP development, and a nonlinear relationship exists between planting density and visible greenery. The results suggest that an optimal planting density may exist for specific combinations of tree species and street type. The findings provide valuable insights into effective tree-planting strategies for enhancing long-term visible greenery in urban streets.