Following the last Russo-Ottoman War of 1877-78, the Russian Empire annexed the ethnically heterogeneous border regions of Kars, Ardahan (today Turkey), and Batum (today Batumi, Georgia) in the Ottoman Empire as war reparations. Ottoman subjects in these locations were permitted to sell their immovable property and immigrate to the Ottoman Empire within three years. This paper traces the spatial development of Kars and Batum after their annexation and in relation to land systems and property rights. Although rarely studied, this territorial shift magnified issues around land, property, and in both the Ottoman and Russian Empires. The Russian administration initially kept the Ottoman land system intact after annexing these territories. However, urban and rural development were urgent in both Kars and Batumi. In this paper, I investigate the work done by the Russian administration’s land commissions to understand, translate, and navigate the Ottoman land regulations in these border towns. Moreover, I examine how the remaining Ottoman subjects in the newly annexed Russian territories further complicated the Russian imperial plans by remaining in place or through land speculation. As such, I argue that these former Ottoman subjects postponed and limited the Russian settlement projects in these previously Ottoman territories. To trace the spatial developments and resistances to them in the South Caucasus borders, I utilize primary sources in Russian, such as newspapers, essays, and annual reports, as well as visual materials such as maps, drawings, and postcards. In doing so, this paper aims to contribute to the scholarship through a study of the built environment of the Caucasus.