Only a limited number of studies have examined land price issues based on official land price maps. A very unique timeline of official land price maps (2006–2019) allowed research to be conducted on four Czech cities (Prague, Olomouc, Ostrava, and Zlín). The main aim of the research was to describe the links between land price, land use types, and macroeconomic indicators, and to compare temporal changes of these links in four cities of different size, type, and structure by using spatial data processing and regression analysis. The results showed that the key statistically significant variable in all cities was population size. The effect of this variable was mostly positive, except for Ostrava, as an example of a developing city. The second statistically significant variable affecting land prices in each city was discount rate. The effect of other variables differed according to the city, its characteristics, and stage of economic development. We concluded that the development of land prices over time was slightly different between the studied cities and partially dependent on local spatial factors. Nevertheless, stagnation in 2010–2011, probably as a consequence of the global economic crisis in 2009, was observed in each city. Changes in the monitored cities could be seen from a spatial point of view in similar land price patterns. The ratio of land area with rising prices was very similar in each city (85%–92%). The highest land prices were typically in urban centers, but prices rose only gradually. A much more significant increase in prices occurred in each city in their peripheral residential areas. The results of this study can improve understanding of urban development and the economic and spatial aspects of sustainability in land price changes.