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I'm Jewish and grew up in Newton, which is pretty comparable to Winchester. Winchester has a moderate sized Jewish population but only one synagogue. I don't know whether that synagogue serves people in Winchester itself or elsewhere. Your child will not be the only Jewish kid there, that I know.
However, Newton and Lexington and near Winchester, are very comparable and have much larger and more varied Jewish communities. Brookline and Newton are the centers of Boston's Jewish population. If you want kosher food, varied synagogues and Jewish schools you are basically limited to Newton, Brookline and Sharon. Lexington has a Jewish community with 3 or 4 synagogues and less of a Jewish feel than Newton or Brookline. However, it has more Jews than Winchester.
I am quite sure you'll be fine in Winchester but the other towns I mentioned have a lot more Jewish life and larger Jewish communities.
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