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If you do a google search of the phrase, it seems to be a common phrase in wills from the past century. It just means that there has been mention of a specific count earlier in the sentence, and in that count, this guy was a schoolmaster. I doubt it implied anything about whether the schoolmaster was employed by a private family or a town or a religious community. I’ve not heard of private family tutors in Delaware. There were many small, town-based schools as well as small academies, in Delaware.

“Said” means “mentioned previously”. So this is just saying either the county or the schoolmaster was already referred to earlier in the document. As stated in another comment, it tells you nothing about who employed the schoolmaster.

I think I found the record you’re referring to on Ancestry (next time you should attach it to make it easier for us to help you). The verbiage is “John Boyd late of said county, schoolmaster …” This means John Boyd is deceased but prior to his death he was a schoolmaster and lived in “said county” - i.e. Kent County, which was the county mentioned earlier on the page.

Are there any related time period?

I manage a small museum in York Co, Pa. We had a large genealogy collection donated this year. Many Boyd files if you have a Pa connection.