Multiscale landscape analysis offers both advantages and challenges in monitoring urbanization and assessing its environmental impacts. In this chapter, we discuss a multifaceted approach to address some challenges associated with scale, which includes examination of the same geographic area at multiple spatial resolutions and extents based on diverse satellite imagery, the use of object-based image analysis and ecologically relevant analysis units to minimize the modifiable area unit problem, and finally separate examinations of landscape change on administrative (social) as well as green infrastructure (ecological) scales. The study site, Stockholm, Sweden, has been experiencing an unprecedented urbanizing trend, and its growing population is placing pressure on green areas that are important for maintaining ecosystem services and biodiversity in the region. We intended to investigate the extent of urbanization in Stockholm and analyze its environmental impacts by evaluating changes in relevant environmental indicators from regional to local scales. We conducted three studies based on optical satellite imagery with different spatial resolutions and varying study area extents. Multiscale analysis, performed both within and between the individual studies, reveals the broader trends of urbanization and the accompanying environmental impacts while also identifying localized environmental hotspots where mitigation measures or transboundary collaboration may be needed. This kind of information can assist urban planning by raising awareness of change trends while also indicating possible starting points for planning conservation measures.