The aim of this paper is to present a novel platform for advanced transmission of medical image and video, introducing context awareness in telemedicine systems. Proper scalable image and video compression schemes are applied to the content according to environmental properties (i.e., the underlying network status, content type, and the patient status). The transmission of medical images and video for telemedicine purposes is optimized since better content delivery is achieved even in the case of low-bandwidth networks. An evaluation platform has been developed based on scalable wavelet compression with region-of-interest support for images and adaptive H.264 coding for video. Corresponding results of content transmission over wireless networks (i.e., IEEE 802.11e, WiMAX, and UMTS) have proved the effectiveness and efficiency of the platform.