Alan Jackson – $28 Million, Tennessee

The best way to describe the deluxe house belonging to Alan Jackson is one word – fairytale! We cannot think of anybody who wouldn’t appreciate the breathtaking, serene view from his home. He bought the land in 1995, and it took nearly two years of hard work to create the stunning home pictured here where he lives with his wife and daughters. However, when it was just the two of them in 2010, they decided to sell. We’d have certainly bought it if we had that insane amount of funds!