On the Market Since: 2015
Total Area: 7,988 square feet
Initial Value: $40 million*

Singer Gloria Estefan put her mansion on Star Island on the market in 2015 for an ambitious $40 million. The property, which her husband, Emilio, purchased, was initially intended for his mother, as there were two guest houses near the mansion. Sadly, his mother passed away, and the Estefans rented out the guesthouses for a couple years before deciding to put the home up for sale.

The Star Island mansion, though beautiful and luxurious, has struggled to sell. The price was recently knocked down in 2019 to $32 million, and, judging from the sluggishness of the market, the “Mi Tierra” singer will likely have to slash the price again.