Just a few years after Alan Jackson put his 19,000 square-foot Franklin, Tenn. estate on the market for a mere $38 million, the 'Chattahoochee' singer is at it again, listing his Floridian Jupiter Island estate for $14.9 million. The property, which hugs South Beach Road from both sides, features a four-yacht dock in the west side of the Intracoastal.

Located on the southern portion of the Martin County Island, the giant homestead also boasts an 8,700-square-foot, two-story mansion which sits right on the beach with nearly 1 acre of dunes on its east side. Jackson bought the estate at a price tag of $3.5 million 10 years ago. In 2006, the Jackson family knocked down the original home and built a new one the following year, which features six bedrooms and five bathrooms. The home has a current appraisal price of about $6.2 million.

To top off the prestige and mystique of this particular piece of property, Jackson isn't the only celeb living in the neighborhood. Sharing his stretch of beach are a series of multi-million dollar mansions with owners ranging from golfer Greg Norman to Tiger Woods and Richard Fuld, former CEO of Lehman Brothers.

If you're in the market for a new mansion and were hoping to purchase from the country great but just can't swing the $14 million, don't fret. Jackson recently dropped the price of his Tequesta, Fla. estate. Though it's a significantly smaller property than at his Jupiter Island home, he's now listed it as $900,000 instead of the former $1.2 million asking price.