Within the contexts of globalization and the Atlantic Forest ecoregion, I present a multiscale analysis of anthropogenic landscape dynamics in the Florianópolis city-region, Santa Catarina, southern Brazil. Drawing on field research conducted between 2000 and 2004 and a review of the literature, I examined Brazilian demographic and agricultural census data for the period of 1970 to 1995–1996. I hypothesized that economic restructuring, new institutional arrangements, and the valuation of environmental amenities and ecosystem services have contributed to forest recovery trends and thus a forest transition in the city-region. My results indicate that along with rapid urbanization, in-migration, socioeconomic polarization, and segregation, the city-region has experienced the contraction of private agricultural land area, expansion of protected areas, recovery of forests, and conversion of coastal plain ecosystems to built environments. Future analyses of forest transition dynamics should consider the spatial configurations of socioeconomic inequality in city-regions.