Background Telemedicine is an emerging concept that involves the use of electronic information and communications technologies to provide and support healthcare. This study aimed to assess the knowledge and attitudes of family medicine residents toward telemedicine in Riyadh, Saudi Arabia. Methodology This was a cross-sectional observational study using a self-administered questionnaire distributed among family medicine residents in Saudi Arabia. The collected data included sociodemographic features, residents' knowledge, and attitudes toward telemedicine. Data were collected in Excel and analyzed using SPSS software version 29. A P-value of less than 0.05 was considered statistically significant. Results The study included 279 family medicine residents with a median age of 27 years. The majority of participants (n=191, 68.5%) had a good level of knowledge regarding telemedicine, which was significantly associated with younger age (p-value = 0.012). Additionally, there was an overall good attitude toward telemedicine attributes, significantly associated with older age and female gender (p-values <0.05). Conclusion This study highlights that family medicine residents in Riyadh, Saudi Arabia, generally possess good knowledge and positive attitudes towards telemedicine. Key findings indicate that younger residents are more knowledgeable about telemedicine, while older residents and female participants show more favorable attitudes toward its attributes. However, further training and education on the ease of use of telemedicine applications are required.