Homograph ambiguity is an original issue in Text-to-Speech (TTS). To disambiguate homograph, several efficient approaches have been proposed such as part-of-speech (POS) n-gram, Bayesian classifier, decision tree, and Bayesian-hybrid approaches. These methods need words or/and POS tags surrounding the question homographs in disambiguation. Some languages such as Thai, Chinese, and Japanese have no word-boundary delimiter. Therefore before solving homograph ambiguity, we need to identify word boundaries. In this paper, we propose a unique framework that solves both word segmentation and homograph ambiguity problems altogether. Our model employs both local and longdistance contexts, which are automatically extracted by a machine learning technique called Winnow.