Alan Jackson – $28 Million, Tennessee

Alan Jackson is a country music singer-songwriter who has built his career around a “traditional country” style of music. He is best known for songs like “Chattahoochee” and “Where Were You (When The World Stopped Turning)”, which he wrote after the 9/11 terrorist attacks. Jackson has recorded 16 studio albums and three blockbuster albums, as well as two Christmas albums and a couple of gospel music albums. During his career, he received two Grammy Awards and 16 CMA Awards.

Alan Jackson lived in a mansion, we can only wish for! Who wouldn’t want to live by the lake! After buying the land in 1995 it took almost two years to build what you see here right now! He shared his fairytale with his wife and their daughters. In 2010, they decided to sell the house because it was too much for just the two of them. If only our credit card allows it, we would be happy to get our hands on that house! But another problem will be insurance money.