The settled landscape in the Drakensberg Mountain region of South Africa is characterized by increasing urbanization. Some of the supposedly rural settlements in the region have experienced increasing change in their landscapes over the last 3 decades, resulting in significant land use and land cover (LULC) changes. Among such settlements, Phuthaditjhaba and its environs are slowly becoming a metropolitan area. Based on conceptual considerations regarding sustainable urban development, we assessed LULC change using 4 Landsat images from 1989, 1999, 2009, and 2019 and a combination of unsupervised and supervised classification methods. The images were classified into 4 LULC classes. Between 1989 and 2019, the urban built-up area in Phuthaditjhaba increased from about 5% to 19%, representing a total increase of 270%. However, the greatest increase in land cover was in bare surface at the expense of vegetated areas, including farmland, which decreased from about 45% to 15%. The increase in bare surface could be due to fires. Built-up areas also increased due to a consistent increase in population density in the study area. We further described spatial patterns in LULC using selected landscape metrics. A decrease in patch density (PD) and cohesion, coupled with constant edge density (ED) and an increase in the fractal dimensional index (FDI), indicates fragmentation and less connectivity between 1989 and 1999; we interpret this as a sign of unsustainability. An increase in PD and cohesion and fluctuations in ED and FDI show that land patterns were more aggregated between 2009 and 2019. At the class level, an increase in PD, cohesion, and ED also showed more aggregated land patterns, which was confirmed by the mean patch size. The FDI revealed greater connectivity, which we also interpreted as unsustainable because of the increase in bare surface and built-up areas. Integrative coplanning and comanagement of land use and allocation are needed to ensure sustainable development.