The objective of the study is to analytically assess the residents’ perception of planning of six housing estates and their satisfaction levels in Benin City, Edo state, Nigeria. The population of the study comprises all residents of the six housing estates in Benin City as at 2018 which is the study period. The data were collected from the six (6) estates covered by this study: Oluku Housing Estate, EDPA Housing Estates Ugbowo, Federal Housing Estate, Oregbeni, Federal Housing Estate on Ikpoba Hill, Iyekogba Housing Estate, Ebo Village, and Andrew Wilson Housing Estate, Evbuoriaria. A total of 1200 copies of questionnaires were administered across the six housing estates. However, the total response rate of 1000 was achieved as only these copies of questionnaires were retrieved in usable format. Descriptive statistical tools such as means, standard deviations, kruskal-willis test and categorical regression analysis were utilized for the data analysis. The result showed that the relative satisfaction index scores for the all the estates are on the fairly satisfied region (RSI: 2.1-3.0) and this implies that residents are fairly satisfied with the estate planning conditions. The Kruskal-willis test confirms the absence of any significant differences in RSI scores across the estates while the categorical regression analysis results shows that estate planning has a positive effect on residents satisfaction and this is significant at 5% (p=0.003) which implies improvement in estate planning results in higher satisfaction levels. The study recommends the need for Government policy to encourage a decent living environment in terms of planning of estates.