The article presents the results of a study of the dynamics of woody vegetation in the territory of Greater Moscow over twenty years (2000–2020). Using Landsat ARD remote sensing data and geoinformation technologies, a series of maps of growth and loss of woody vegetation were constructed based on reflectivity values, brightness temperature, and vegetation indices. When calculating the areas of forests and fields, it was found that over 20 years their area has slightly increased overall. It was found that the increase in woody vegetation in Old Moscow is characteristic mainly of residential areas close to the Moscow Ring Road. In TiNAO, the maximum increases in woody vegetation are evenly distributed across the districts. In nature protected areas, as a rule, there is no significant increase. Losses of woody vegetation in protected areas are associated with their landscape transformation and construction of various structures. The greatest forest losses are observed in the residential areas of Old Moscow, not directly adjacent to the Moscow Ring Road. In New Moscow, there are lines of transport arteries and areas oriented towards development. Of the specially protected natural areas, the greatest forest losses are typical for the Losiny Ostrov National Park. Of the natural and historical parks, Izmailovo, Kuzminki-Lyublino, Tsaritsyno, and Moskvoretsky Park suffered the most. The territories of the specially protected natural areas are mainly characterized by the stability of their tree stands, not distinguished by either strong growth or large losses. An assessment was made of changes in the areas of forest growth and loss in the city as a whole by tree height categories, which found that the greatest growth is typical for categories 5, 7, 9–13 m, and the greatest losses are for categories 12, 18, 19, and 21 m. The territories where the tree height did not change also have a small share in the city area (about 1.5 %). The data obtained can be recommended for studying the history of the city, developing urban planning and environmental protection measures.