Born in Knoxville, Tennessee, Kenny Chesney had the makings of a country singer from an early age. After receiving his first guitar, Chesney quickly discovered his passion for music. In 1989, he self-released a demo album that sold 1,000 copies—an impressive feat given the lack of a major marketing push at the time. Though Chesney grew up in the landlocked town of Knoxville, his love for the ocean is clear, as he’s made several real estate investments in the Caribbean.
Among his prized properties are a home in Upper Peter Bay, another residence called the Stoneridge house off Centerline Road, and a property in Estate Chocolate Hole, all located on the island of Saint John in the US Virgin Islands. These properties are managed under the Grigsby Farm Trust, a legal entity representing the country star. With an estimated net worth of $225 million, Chesney has the financial freedom to invest heavily in luxury real estate, reflecting his love for island living and a lifestyle that blends success with serenity.
