On the Market Since: 2019
Total Area: 11,173 square feet
Initial Value: $44.5 million*

When it comes to Hollywood couples, Brad Pitt and Jennifer Aniston really had it all. Not long after they tied the knot in 2000 they bought an incredible 11,173 square foot mansion in Beverly Hills. Of course, they added their own touches like a guest house and a tennis court, which only added to the value. 

After the split, the house was sold to an executive, who later put it back on the market in 2019. You may think that it would’ve sold like lemonade in a drought, but that wasn’t the case. It took over a year for a suitable buyer to seal the deal – though the same buyer has reportedly put the house on the market again.