Online secondhand resale platforms are a booming industry involving the growing recognition of various economic, environmental, and recreational benefits in buying and selling used items. This preliminary study explores technology-based strategies for online secondhand platforms, which contributed to the resale industry’s steady growth and digital transformation. Through a variety of literature, this study established a basis for developing research on technological innovations in online resale platforms. A mixed method was used to collect both quantitative and qualitative data to investigate and understand the features of resale e-commerce. Case studies of four online secondhand resale platforms specializing in general goods and fashion helped identify a variety of technological strategies that were later analyzed based on the technology acceptance model (TAM). Survey data from respondents in their twenties and thirties living in South Korea indicated features that promote safe transactions, engaging user experience and user interface design, and individual compatibility as most effective in influencing users’ resale platform usage. Features that involve high technology, such as virtual reality and machine learning, had the least impact on users’ usage. Data gathered from follow-up interviews showing the recurring theme of unfamiliarity with the technological features corroborated the survey findings. Analyzing qualitative data from expert interviews generated key concepts in future trends in online resale platform strategies, including effective data management. Based on this study’s findings, the digitalization and onlineization of the online secondhand resale industry are likely to continue with the implementation of various strategies that contribute to users’ perceptions of usefulness, ease-of-use, and enjoyment, increasing users’ satisfaction and, hence, the actual usage of these platforms. The proliferation of secondary e-commerce will facilitate a shared culture that values sustainable consumption in online platforms and promote sustainability in the retail industry.