The purpose of this study is to investigate pre-service elementary teachers' realistic considerations and difficulties in solving "division with remainder" type of problems which focus on the measurement meaning of division operation. The qualitative research method of case study design was used for the study. The purposive sampling method was used to determine the participants. A total of 60 senior pre-service teachers who had already taken mathematics teaching courses participated in the study. They were enrolled in the Elementary Teacher Education Program of the Faculty of Education in Turkey in 2018-2019 academic year. The data collection tool included a problem based questionnaire and semi-structured interviews to obtain a detailed description of participants' difficulties related to division with remainder problems. The questionnaire included four groups of problems according to the types of the remainder: Remainder Divisible, Remainder Not Divisible, Remainder as the Result, and Readjusted Quotient by Partial Increments. Based on Verschaffel, De Corte and Lasure's (1994) framework, participants' answers to the problems were analyzed and categorized into four groups as "realistic answer, expected answer, arithmetic error, and other error". The findings showed that the pre-service teachers' answers were mostly coded under the Realistic Answer category compared to the other categories.