(1) Contemporary approaches to sustainable housing design tend to prioritize technological solutions supporting energy efficiency and climate change mitigation. On the contrary, spatial planning of housing estates does not always address all pro-ecological aspects, such as the role of greenery. This research aimed to assess the greenery content and its environmental importance in typical housing districts in the selected study area. (2) The research methodology was based on indicators reflecting the biologically active area ratio, the length of communication routes lined with trees, the tree number per area unit, the tree canopy, and the environmental benefits delivered by the trees. The above indicators allowed us to compare selected models of suburban residential districts typical of specific timeframes. (3) The results indicated that the greenery content and its environmental benefits in suburban districts are decreasing in the study area. Another finding concerned the importance of selecting tree species for their ability to develop a canopy and provide ecosystem services. (4) The proposed methodology, based on inter-related indicators, validly compared the greenery content in the analyzed districts, giving it application value. The problems observed contributed to the proposal of a revision of Poland’s planning practices. Local zoning plans could include streetscape standards, indicating paving solutions and plantings to improve the situation.