After initial withholdings, you'll typically keep about 53-70% of your Massachusetts lottery winnings, depending on the prize size and your income. Federal withholding is 24% over $5,000, state is 5% over $600, but final federal taxes could add up to 37% total. For a $500,000 prize, expect $120,000 federal withholding and $25,000 state, leaving $355,000 initially; filing might add $50,000 more federal if you're in a high bracket, netting about $280,000. This is an estimate—track your total income and deductions accurately by working with a tax advisor.