The purpose of this study is to design an adaptive and intelligent individualized e-learning environment based on learning style and expert system named UZWEBMAT and to evaluate its effects on students’ learning of the unit of probability. In the study, initially, learning objects were prepared in three different ways in relation to Visual–Auditory–Kinesthetic (VAK) learning style for each subject of the probability unit. These were appropriate for secondary school mathematics curricula. Then, they were transferred into the digital environment. Each student may follow a different course, and the solution supports s/he will get may also differ highlighting the individual learning. The sample of the study consists of 81 10th grade students from two high schools in Trabzon, Turkey. Qualitative and quantitative data were collected from students to answer research questions. Quantitative data were given as frequency distribution and percentages. Qualitative data were analyzed using qualitative data analysis methods. Results of the study indicated that opinions regarding UZWEBMAT are rather positive. Aiming at individual learning, UZWEBMAT provides the most appropriate environment for students. In addition, UZWEBMAT can be used as well to reinforce traditional classroom education.