Despite Buying a $42 Million Dream House in Massachusetts, Dave Portnoy Tells Shannon Sharpe Why His Primary Residence is in Miami

Dave Portnoy, the founder of Barstool Sports, has not always been a man of incredible wealth. These days, though, he’s on top of the world. His net worth, per celebritynetworth.com, is an estimated $150 million.

Money like that gives a person the ability to do a lot of things. It lets Portnoy attend whatever sporting event he chooses, wherever it may be in the world. When he’s not at a basketball arena, ballpark, or stadium, though, he’s at one of his four real estate properties. One of those, in Nantucket, is his so-called “dream house.” Despite this, it’s not where he lives most of the time.

Portnoy’s revelation – and reasoning – for this came during his appearance on Club Shay Shay. He told host Shannon Sharpe that he lists his Miami home as his primary residence so he can keep a larger portion of his income.

“[I’ve] got a Nantucket house. That’s my dream house… richest house in Massachusetts history… when I started Barstool, I would go there for a day. Couldn’t even get a hotel. It’s an expensive place… [but my] primary [residence] is Miami [because of] taxes… you got to [do it that way],” he revealed.

Massachusetts taxes personal income at a 5% clip. Florida, meanwhile, has no state income tax. The differential allows Portnoy to pocket a lot more of his income. That, in turn, enables him to afford luxuries like the lavish Nantucket property. It’s an example of Portnoy letting his money build upon itself.

“Once you get [money], it’s easy to get a lot more… it took me 10 years to make anything. [Now,] if you were like, ‘hey, Dave. You got to go make an extra $5 million in the next week,’ I could do that… when I really got a lot [of money], I spent five hours just talking about the interest I was getting on it. I couldn’t believe it.”

As Portnoy mentioned, his purchase of his Nantucket home is the largest housing transaction in Massachusetts history. And the lofty price tag is warranted. It sits right on the water and comes with some incredibly expensive furniture.

Forbes broke down Portnoy’s purchase in 2023:

“The 1.2-acre pair of waterfront properties… feature a 5,200-square-foot main estate with a two-bedroom guest house and pool in Nantucket’s Monomoy neighborhood, giving the homeowner a sunset view over Nantucket Harbor and the island’s historic downtown… Nantucket, which boasts a wealthy summer population, is also home to a cast of billionaires and celebrities… including former General Electric CEO Jack Welch, designer Tommy Hilfiger, billionaire investor Charles Johnson, billionaire banker Charles Schwab, Fidelity Investments CEO Abigail Johnson, New England Patriots coach Bill Belichick and Red Sox and Liverpool FC owner John Henry.”

Portnoy may not live in the house full-time, but he loves posting pictures of the bay when he is there.

Portnoy’s favorite NBA team, the Boston Celtics, was recently eliminated from the NBA playoffs. Now, he’ll turn his attention to the Red Sox’s and Patriots’ quests for championships.