Kenny Chesney – Saint John, US Virgin Islands, $11 Million

Born in Knoxville, Tennessee, Kevin Chesney had the early makings of a country singer. He received his first guitar at an early age and when he started fiddling with it, he knew that he would go into the music industry. He self-released a demo album in 1989, which surprisingly sold 1,000 copies, despite the absence of a powerful marketing arm.

Life is definitely good for country singer Chesney. It seems that even if he was born and raised in landlocked Knoxville, Tennessee, Chesney loves the ocean. That’s why he has multiple investment properties in the Caribbean, particularly in Saint John, US Virgin Islands. One of them is this property in the Upper Peter Bay, another one is the Stoneridge house located off of Centerline Road, and lastly, a house in Estate Chocolate Hole. All of his properties are owned by the Grigsby Farm Trust, an entity that represents the famous country star. With a $225 million net worth, it’s not surprising that Chesney would invest handsomely in real estate properties.