After selling his sprawling Manalapan estate for a record price in June, the tech billionaire bought a more modest mansion in Wellington for $12 million in September.
Clark, who began amassing his fortune decades ago as the founder of Netscape, WebMD and Silicon Graphics, now has a net worth estimated at $2.9 billion.
And when it comes to spending money, Clark likes yachts, expensive real estate and funding startups.
In 2018, he sold the Palm Beach property known as Il Palmetto for $85 million, and in 2016, he put it on the market for $137 million.
But that deal pales in comparison to the one he sold to a fellow billionaire last summer.
The saga of the massive property known as the Gemini began in 2015 when the Ziff family put the famous property on the market for $195 million.
The site sits on a 16-acre barrier island that offers extensive frontage on the Atlantic Ocean and Intracoastal Waterway.
The property's main house measures a staggering 62,000 square feet.
It is connected to the guesthouse on the waterway via an air-conditioned tunnel.
The property has three additional guesthouses, as well as management and staff apartments and offices.
Understandably, the number of potential buyers shopping in the nine-figure price range is very small.
Even smaller are the buyers who buy ready-made hideaways in the Sunshine State, and the maintenance that comes with them.
Two years passed without a single buyer; so in May 2017, Ziff's heirs lowered the price by 15 percent.
Back on the market at $165 million, the Gemini remains one of the most expensive homes for sale in the United States.
In November 2017, the price was further slashed to $137,500.
At the peak of the COVID-19 pandemic in August 2020 - when luxury buyers fled to Florida in droves - prices were further slashed to a billionaire-friendly $115 million.
With no buyers in sight, locals were reportedly reluctant to part with the sprawling estate.
But Clark stepped up to the plate and purchased the Gemini in March 2021 for $94,173,300, which was less than half of its initial asking price.
Clark later said modestly that the purchase was a spur-of-the-moment decision.
In the process, he even pushed fellow billionaire Oracle founder Larry Ellison aside.
It ended up being a profitable acquisition for Clark, who sold the home 15 months later for $173 million to, yes, Ellison.
That's an 84% return on investment, which is certainly better than parking your money in a CD.
Fresh off the sale of the Gemini to Ellison, Clark's 2000 S. Ocean Trust bought a smaller property in Wellington, about 15 miles west of Palm Beach.
The seven-bedroom, 9,830-square-foot home is part of the Palm Beach Polo Golf and Country Club.
Described as a British West Indies-style estate, the four-bedroom house has a wine room and a chef's kitchen.
A separate two-bedroom guesthouse comes with a gym that can be converted into an additional bedroom.
Clark purchased the house from international equestrian Ellen Van Dyke Hortges.
The affluent town is also home to Bill Gates, who purchased a number of homes in Wellington to support his daughter's equestrian sport.