[en] The political, economic, and social changes associated with the collapse of the Soviet Union at the end of the 1980s led to major land cover and land-use changes in the southeastern Baltic Sea coastal regions. These changes (demilitarization of the coasts, end of collective ownership, specialization of economic activities, etc.) are characterized by a fast process of coastalization with the growth of urban areas, coast suburbanization, and the decrease of agricultural land. At the same time, we observe the implementation of protected natural areas at the regional level and through cross-border cooperation with international organizations (UNESCO, European Union [EU], etc.). Both processes have an important impact on the management of the coastlines of Latvia, Lithuania, and Russia. The analysis of the coastal changes is based on the use of Landsat remote sensing data series from the 1980s to 2020 combined with EU geographic databases and the land-use plans. The comparative analysis of the land cover changes in the Oblast of Kaliningrad, Lithuanian, and Latvian coastal zones allows us to understand the impacts of the three different planning policies since the end of the 1980s. The territorial dynamics are modelled using the GEOBIA package with object-oriented classification and machine-learning algorithms (maximum likelihood, minimum distance to means, parallelepiped classifiers) applied to the Landsat 5 TM and Landsat 8 OLI satellite multispectral images. The produced land cover maps are compared with the Climate Change Initiative Land Cover of the European Space Agency from 1995 to 2015.