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As far as the Bay State is concerned, similar to a number of states throughout the country, Massachusetts began turning the wheels on legal sports betting in late 2018. It's not a matter of wondering if Massachusetts online sports betting will become a legal reality or not; it's instead a matter of when legal Massachusetts sports gambling will come to fruition. New Customer Offer. 21 years of age or older to wager. org for 24/7 support. Having launched online sportsbooks as of Mar.