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Estonia is a small country at the coast of the Baltic Sea. Its area is slightly more than 45 thousands of square kilometres, the population is approximately 1.3 million people, and the coast line is 3800 kilometres long. Estonian culture is closely connected with the sea and the land. Thus, researchers have been very interested in exploring Estonian landscapes and landscape processes over time. Landscape is a continuously changing phenomena, every place and location has a unique landscape. One possibility for identifying the character of a certain place and to investigate the preserved landscape elements is to explore the changes in landscapes over time. Estonian cultural landscapes and landscape heritage have been valued and actively explored for many years. Preservation of the unique Estonian landscape image is considered as an important issue. This article introduces the study, which focused on exploring the changes in landscape and settlement structure.