Kenny Chesney – Est. $11 million, St. John, US Virgin Islands

Kenny Chesney, the country music sensation, has rolled out more than 30 million albums, and he also happens to be one of the most successful touring musicians in the country music circuit. All of his records have either been certified gold or even higher by the trade organization RIAA. The country music star is one of the most successful crossover artists ever.

The $225 million of net worth that Kenny has piled on has enabled him to lay his hands on a few upmarket properties across the Caribbean Islands. However, his Upper Peter Bay pad is one that is undoubtedly the best of the lot. We heard that Kenny spent a staggering $11 million to acquire the property.