Two experiments investigated age differences in how semantic, syntactic, and orthographic factors influence the production of homophone spelling errors in sentence contexts. Younger and older adults typed auditorily presented sentences containing homophone targets (e.g., blew) that were categorized as having a regular spelling (EW) or an irregular spelling (UE). In Experiment 1, homophones were preceded by an unrelated word, a semantic prime that was congruent with the target's meaning in the sentence (e.g., wind), or a semantic prime incongruent with the target's meaning (e.g., sky) and instead related to the competitor homophone. Experiment 2 manipulated the target's part of speech, where target and competitor homophones shared or differed in part of speech. For both age groups, significant semantic priming occurred, where homophone errors decreased following congruent semantic primes and increased following incongruent primes. However, priming only occurred when homophones shared part of speech. Further, both age groups made more errors on homophones with an irregular than a regular spelling, and this regularity effect was smaller for older adults when homophones shared part of speech. Contrary to many spoken production tasks, older adults made fewer errors overall than younger adults. These findings demonstrate age preservation in lexical selection but age differences in orthographic encoding, resulting in older adults producing fewer errors because of reduced activation to competitor homophones. These findings also illustrate that syntactic factors, such as part of speech, can influence the spellings of individual words.