Cities in Afghanistan have been rapidly urbanized; however, many parts of these cities have been developed with no detailed land use plan or infrastructure. In other words, they have been informally developed without any government leadership. The new government started the In-situ Upgrading Project in Kabul to upgrade roads, the water supply network system, and the surface water drainage system on the existing street layout in 2002, with the financial support of international agencies. This project is an appropriate emergency improvement for living life, but not an essential improvement of living conditions and infrastructure problems because the life expectancies of the improved facilities are as short as 10–15 years, and residents cannot obtain land tenure in the unplanned areas. The Land Readjustment System (LRS) conducted in Japan has good advantages that rearrange irregularly shaped land lots and develop the infrastructure effectively. This study investigates the effects of the In-situ Upgrading Project on private investment, land prices, and residents’ satisfaction with projects in Kart-e-Char, where properties are registered, and in Afshar-e-Silo Lot 1, where properties are unregistered. These projects are located 5 km and 7 km from the CBD area of Kabul, respectively. This study discusses whether LRS should be applied to the unplanned area based on the questionnaire and interview responses of experts experienced in the In-situ Upgrading Project who have knowledge of LRS. The analysis results reveal that, in Kart-e-Char, a lot of private investment has been made in the construction of medium-rise (five- to nine-story) buildings for commercial and residential purposes. Land values have also incrementally increased since the project, and residents are commonly satisfied with the road pavement, drainage systems, and water supplies, but dissatisfied with the poor delivery of electricity as well as the lack of public facilities (e.g., parks and sport facilities). In Afshar-e-Silo Lot 1, basic infrastructures like paved roads and surface water drainage systems have improved from the project. After the project, a few four- and five-story residential buildings were built with very low-level private investments, but significant increases in land prices were not evident. The residents are satisfied with the contribution ratio, drainage system, and small increase in land price, but there is still no drinking water supply system or tenure security; moreover, there are substandard paved roads and a lack of public facilities, such as parks, sport facilities, mosques, and schools. The results of the questionnaire and interviews with the four engineers highlight the problems that remain to be solved in the unplanned areas if LRS is applied—namely, land use differences, types and conditions of the infrastructure still to be installed by the project, and time spent for positive consensus building among the residents, given the project’s budget limitation.