The agricultural mountain landscape in the Romanian Carpathians follows the same change trend in other European mountains, from variety and individuality to simplification and uniformization. Our paper proposes two complementary case studies from the Southern Carpathians—Poiana Mărului and Fundata, representative areas for the entire Carpathian ecoregion. The research focuses on a remote sensing approach with Corona KH-4B (1968) and Planet Scope (2018) images at 2.0–3.0 m resolution used for mapping arable plots pattern and size change. Landscape transformation modelling is focused on four-hectare sampled grid for both case study areas, followed by a landscape metric analysis. Fundata area is the most transformed, where arable plots disappeared under the service-based economy pressure. Poiana Mărului shows an earlier stage of landscape transformation, where the arable land abandonment process is incipient. The spatial and statistical analysis and field survey confirmed that tourism changed the traditional agricultural landscape, generating potential environmental conflicts and indicating the sustainability degree.