The purpose of this research is to develop contextual mathematical thinking learning model which is valid, practical and effective based on the theoretical reviews and its support to enhance higher-order thinking ability. This study is a research and development (R & D) with three main phases: investigation, development, and implementation. The experiment consisted of 78 Junior High School students who were divided into two groups, namely experimental group and control group. The model development phase results the syntax of contextual mathematical thinking learning model which are as follows: (1) presentation of the contextual problems; (2) asking the critical and analytical questions; (3) individual and group investigation; (4) presentation and discussion; (5) reflection; and (6) higher-order thinking test. The implementation phase concludes the contextual mathematical thinking learning model which can be applied effectively to enhance the students' higher-order thinking ability. This model is able to intensify higher-order thinking ability at high category. The observation of learning activities was seen in the main elements of learning model which are syntax, social system, reaction principle, support system, instructional impact, and accompanist impact. The three main elements were observed by the observer and showed an average in the good category: syntax has an average of 3.5, social system has an average of 3.52, and reaction principle has an average of 3.47. This model is recommended for mathematics learning activities in the classroom to support the improvement of higher-order thinking ability. Contextual problems can be presented to the local cultural context that allows students to learn mathematics in a real context.