In this study, the authors examined the relationship between students’ life satisfaction, school engagement, and confidence in the classroom. An analysis was performed of how students’ life satisfaction differs according to their housing, school type, and classroom level. The multidimensional student satisfaction scale, confidence scale in the class, and school engagement scale were used to collect data from a sample of 287 high school students. In this study, Pearson correlation coefficient, path analysis, t-test, Welch test, and Tamhane’s T2 test were used to analyze the data. Goodness-of-fit indices concerning the path analysis demonstrate how variables such as school engagement and confidence in the classroom predict students’ life satisfaction, indicating that the model is acceptable. The model can sufficiently explain the relationship between the observed and implied variables (x2 = 209.69, df = 60, x2/df = 3.49, p = 0.00, RMSEA = .09, NFI = .92, NNFI = .93 CFI = .94, IFI = .94, RFI = .90, GFI = .88, AGFI = .82, and SRMR = .07). The results indicated that the life satisfaction of high school students decreases as the grade level increases. It was found that students who live in school dormitories have higher life satisfaction than those who reside with their families. In addition, it was found that students who study at fine arts high schools and sports high schools have higher life satisfaction than those who study at regular high schools.