Research Highlights: Differentiation of Scots pine forests of the class Vaccinio-Piceetea in Poland has been the subject of numerous studies, including revisions. Despite that, the area of southwestern Poland was hitherto practically unexplored in this respect. Background and Objectives: The aim of this work was therefore (i) to present the diversity of the pine forests in the Sudetes and their foreland; (ii) to compare the ecology of studied communities. Materials and Methods: We analyzed 175 phytosociological relevés collected between 1991 and 2020 in natural and anthropogenic pine stands. To identify vegetation types, we used the modified TWINSPAN algorithm; principal coordinate analysis, distance-based redundancy analysis and permutational tests were applied to identify the variation explained and the main environmental gradients shaping the studied plant communities. Results: Five associations were distinguished: thermophilous Asplenio cuneifolii-Pinetum sylvestris Pišta ex Husová in Husová et al. 2002, which develops on shallow soils over ultrabasic substrates, Hieracio pallidi-Pinetum sylvestris Stöcker 1965, which prefers outcrops of acidic rocks; Betulo carpaticae-Pinetum sylvestris Mikyška 1970, which is relict in origin and occurs on the upper Cretaceous sandstones, the peatland pine–birch forests of the Vaccinio uliginosi-Betuletum pubescentis Libbert 1933 and the Vaccinio myrtilli-Pinetum sylvestris Juraszek 1928. Moreover, community Brachypodium sylvaticum-Pinus sylvestris with the occurrence of many thermophilous and basiphilous species was also found on limestone substratum. The analysis of the species composition of pine plantations established on deciduous and mixed forests habitats revealed that these anthropogenic communities were marked by a random combination of species in which a certain group of common forest generalists participated. The distinguished communities differed clearly among each other also in habitat characteristics. Particularly important for their differentiation were soil reaction and nutrients, supported by differences in moisture, temperature and light availability. Apart from the edaphic factors, altitude and the bedrock type proved to be equally important. Conclusions: Our study provides new remarks to the typology and synecology of pine forest communities in SW Poland.