Attention Tax Professionals You have many opportunities to meet new clients all over the world as a TaxConnections Member. The way to meet a steady stream of propsective new clients is by engaging with our global visitors through TaxConnections "Ask Tax Questions" Feature. As a professional gambler who travels all over the world gambling in land based casinos all over the world for ten years, I have heard that taxes on gambling winnings are tax free in Estonia. For this reason, I am planning on moving to Estonia but need confirmation prior to making this decision. If I move to Estonia and become a resident will all my gambling winnings be tax free?