Scottie Pippen – $2.23 million, Chicago

Scottie Pippen is one of the best basketball players that the city of Chicago has ever seen. Now that he’s been retired for a couple of decades, he treats his beautiful Chicago property as “sort of his vacation house.” Without a doubt, his Mediterranean-inspired home in Chicago has a few amenities that can easily make it the perfect place for an escape. He purchased this home back in 2004 with his then-wife Larsa Pippen for $2.225 million. He’s currently looking to sell it, and for a cool price of $1.899 million, the Chicago residence can be yours!

Pippen’s sprawling 10,000-square-foot mansion sits on a 2.6-acre land in the exclusive Chicago suburb of Highland Park. It comes with six bedrooms, five bathrooms, and celebrity-grade amenities, including a sauna, a movie theater, a game room, and a wine cellar. It also sports tons of Scottie Pippen memorabilia and a custom-built indoor regulation-sized basketball court. The property is undoubtedly massive, so make sure you take into account the insurance and maintenance costs that’ll come with the purchase!