On the Market Since: 2016 
Total Area: 5,500 square feet
Initial Value: $29.5 million*

Supermodel Christie Brinkley’s Hamptons home looks like something out of a fairytale, with its tower surrounded by dense forest. Brinkley scooped up the mansion for $10 million, and she was able to sell it for well over what she got it for in 2019, selling it for $17.999 million (though the original asking price was $25 million).

Brinkley originally put it on the market in 2010, but she took it off in 2011, only to put it back on the market in 2016. The 5,500-square-foot mansion was built in 1843. It has five bedrooms, five-and-a-half bathrooms, and three stories of living space, all finished with period details from the 1800s.