Modern school environments put emphasis on adequate and qualitative facilities to promote conducive teaching and learning environments, the deplorable conditions of the primary schools has become worrisome to the state government and education stakeholders. The study investigated the school environment and pupils' satisfaction with schooling in Ondo State. Two hypotheses were formulated and tested. The descriptive survey design was adopted for the study and a multi-stage sampling technique was used to select 900 respondents from both public and private primary schools within the state. The instrument for the study was a questionnaire which sought information on pupils' level of satisfaction with the school environment. The test retest method of reliability was used in determining the reliability of the instrument, a reliability coefficient of 0.89 was obtained. The data were analyzed with Statistical Package for Social Sciences (SPSS) using percentages, mean, standard deviation, t-test and Spearman rho to test the hypotheses at the 0.05 level of significance. The study found out that pupils in compliant schools were more satisfied with schooling than pupils in non compliant schools. It was recommended that adequate facilities should be provided for the non compliant schools to make pupils derive satisfaction with schooling.