Linda, I'm not an expert on dating charm bracelets or on charms or charm bracelets but it's an interesting subject! Could you take closer photos of the charms that you are asking about as well as the other charms, and give some measurements? The metal color looks like silver tone on my monitor. The charm with a snake wrapped around a sword might be (according to a search I just did): The symbol with one snake and a staff (not a sword) is the Rod of Asclepius. Two entertwined snakes and a winged rod is a Caduceus.
As you know, charm bracelets can be added to over many years but my guess on this one is 1930s. I know you're really busy but if you could get clearer closeups of the charm with the snake and the circular ones on either end someone might be able to tell you what they are. Whatever they represent - it's really "charming." My 1930s guess is based on the scale of the bracelet, the brass chain, the radio cabinet style, the eyeglasses style and the really small scale. I am not an expert on charm bracelets and welcome what others may think.
FWIW: The star charm is an Order of the Eastern Star design--so, yes, Masonic-related. Looks like the sword/snake charm is one of their symbols, also. https://en.wikipedia.org/wiki/Order_of_the_Eastern_Star
