Assessing the relentless expansion of built-up areas is one of the most important tasks for achieving sustainable planning and supporting decision-making on the regional and local level. In this context, techniques based on remote sensing can play a crucial role in monitoring the fast rhythm of urban growth, allowing the regular appraisal of territorial dynamics. The main aim of the study is to evaluate, in a multi-scalar perspective, the built-up area expansion and the spatio–temporal changes in Ilfov County, which overlaps the surroundings of Bucharest, capital of Romania. Our research focuses on processing multi-date Landsat satellite imagery from three selected time references (2000, 2008, 2018) through the supervised classification process. Further on, the types of built-up area dynamics are explored using LDTtool, a landscape metrics instrument. The results reveal massive territorial restructuring in the 18 years, as the new built-up developments occupy a larger area than the settlements’ surface in 2000. The rhythm of the transformations also changed over time, denoting a significant acceleration after 2008, when 75% of the new development occurred. At the regional level, the spatial pattern has become more and more complex, in a patchwork of spatial arrangements characterized by the proliferation of low density areas interspersed with clusters of high density developments and undeveloped land. At the local level, a comparative assessment of the administrative territorial units’ pathway was conducted based on the annual growth of built-up areas, highlighting the most attractive places and the main territorial directions of development. In terms of the specific dynamics of built-up areas, the main change patterns are “F—NP increment by gain”, followed by “G—Aggregation by gain”, both comprising around 80% of the total number of cells. The first type was prevalent in the first period (2000–2008), while the second is identified only after 2008, when it became the most represented, followed in the hierarchy by the previously dominant category. The spatial pattern differentiations were further explored in three complementary case studies investigated in correlation with socioeconomic data, revealing a heterogeneous landscape.