Urban landscapes have become widespread as urban areas have grown. Studying the urban environment in terms of the ecosystem services provided is a key trend in contemporary science. This article aims to examine selected popular typologies of residential streetscapes in terms of their tree species diversity and the health of their greenery. The method combined an on-site tree inventory and selected indices relevant to the species richness, diversity, evenness, and nativity. Their correlation with the Vegetation Indices (VIs), expressing the health of the greenery and its density, was assessed. The main findings included the identification of positive correlations between the mean VI values and the diversity and evenness indices and a negative correlation with the tree nativity. The diversity and evenness indices could be used to inform landscape planning decisions and to evaluate both existing and projected treescapes. The nativity of trees should not be prioritized during planting selection; rather, the soil and climate conditions should be considered. As a result of this study, a comprehensive framework for assessing the greenness of streetscapes was developed. Its implementation will aid in directing greenery planning in residential areas towards sustainable development and regenerative urbanism.