Location: St. John, U.S. Virgin Islands
Price: $7.9 million
Square footage: 9,742
A prolific performer who rose to fame in the ’90s wave of new country, Kenny Chesney is more likely to wear a ball cap than a cowboy hat on stage. Chesney has 15 albums under his belt, of which 14 went gold or higher. This probably helped him purchase his Stoneridge estate on St. John (one of a reported collection of three St. John properties). The estate overlooks Caneel Bay and the North Shore, and is set on national park lands.
Stoneridge has been on the market for years, beginning with a $14 million asking price in 2008, which at the time matched the top price any property had sold for on St. John. In addition to not being able to sell Stoneridge, Chesney has had some other strange luck on the domestic front—his Nashville lakefront home flooded in 2010 and more recently, an intruder who claimed to be dating Chesney was caught trespassing on his property.