A transcoding system and method effectively synchronize segmentation metadata with A/V content when converting an MPEG stream to another format stream using a segment browser. The transcoding system includes a timing synchronizer, which adjusts the timing parameters so that the video data can be synchronized with segmentation metadata even after the transcoding process, a transcoding condition determiner, which determines transcoding conditions suitable for an end user environment, and an encoder, which compresses a video sequence reconstructed from the video data according to the transcoding conditions determined by the transcoding condition determiner and records a presentation time stamp, which is one of the adjusted timing parameters, in the compressed video sequence.