If you’ve spent any time watching Shark Tank, you know Kevin O’Leary isn’t exactly a man of few words. He’s loud. He’s opinionated. And lately, he’s been very vocal about where he’s putting his money and his zip code. For years, people associated "Mr. Wonderful" with the snowy streets of Toronto or the brownstones of Boston. But things have changed. If you're asking does Kevin O’Leary live in Florida, the answer isn't just a simple yes—it’s a calculated business move that involves millions of dollars and a very public spat with the tax code.
He’s officially made the jump. Honestly, it wasn't even a quiet exit. O’Leary has been shouting from the rooftops (and on Fox Business) that he’s traded in his life as a "Boston guy" for the humid, tax-friendly air of Miami Beach.
Why Mr. Wonderful Decided to Call Florida Home
Kevin O’Leary doesn't do anything without a spreadsheet. He’s famously obsessed with "tax efficiency," which is just a fancy way of saying he hates giving the government a nickel more than he has to. For a long time, he lived in Massachusetts. He raised his kids there. He still owns a house there. But according to him, the state became "uninvestable."
In various interviews throughout 2024 and 2025, O’Leary pointed the finger directly at political figures like Senator Elizabeth Warren. He basically claims that high-tax states are "losers" in the competition for capital. Massachusetts increased state income taxes on high earners—often called the "Millionaire’s Tax"—moving the rate from 5% to 9%. For someone like O'Leary, that’s a massive chunk of change.
So, he did what any shark would do. He left.
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By moving to Florida, he effectively gave himself a 9% raise on his income because Florida has zero state income tax. That’s a huge deal when you’re pulling in millions from royalties, television deals, and venture capital exits. He’s not alone, either. He often mentions that most of his neighbors in Miami are former Bostonians who reached the same breaking point.
The Miami Beach Lifestyle
He isn't just living in Florida; he's living the Florida dream. Specifically, he has been linked to the Miami Beach area. This isn't just about the money, though that's the primary driver. It’s also about the ecosystem. Miami has become a massive hub for finance and "crypto-preneurs," which aligns perfectly with O’Leary’s recent business interests.
- Tax Haven: No state income tax, no inheritance tax.
- Business Climate: He calls Florida a "winning state" because of its pro-business regulations.
- Weather: Let’s be real, a 70-degree winter beats a Boston blizzard every single time.
It’s interesting to note that while he claims Florida as his primary residence, he hasn't completely severed ties with his other "nests." He’s a citizen of Canada, Ireland, and the UAE. He still keeps a presence in Toronto—which he calls the fourth largest city in North America—and he still maintains that home in Boston. But for tax purposes? He’s a Floridian through and through.
The Legal Side: Is He Really a Resident?
You can't just say you live in Florida and call it a day. The IRS and state tax boards are like hawks when it comes to wealthy people moving for tax reasons. To be considered a Florida resident for tax purposes, you generally have to spend 183 days or more in the state.
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O'Leary has been very careful about this. In a 2025 legal filing in the Southern District of Florida (a defamation lawsuit against a crypto influencer), O’Leary officially identified himself as a "citizen of Canada" who "resides in Miami-Dade County, Florida." When you’re putting that on federal court documents, you aren't kidding around.
It’s Not All Sunshine and Cheap Taxes
While he loves to praise the state, living in Florida in 2026 isn't without its headaches. O’Leary is a realist. He knows the "Florida premium" is real.
Even if you save on income tax, other costs are exploding. Home insurance in Florida has become a nightmare. Some residents have seen their premiums jump 40% in a single year. Finance experts like Suze Orman have even talked about "self-insuring" because the quotes are so high. O'Leary has noted that while the tax climate is great, you have to be smart about where you buy because of rising sea levels and the "special assessments" hitting condo owners after the Surfside tragedy.
He’s even mentioned that while he moved to Florida, he’s looking at other "winning" states like Texas and the Dakotas for future projects. He’s always looking for the next deal.
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What Most People Get Wrong About His Move
A lot of people think O’Leary moved because he "hates" Massachusetts or Canada. That’s not quite it. He’s actually quite sentimental about Boston—it’s where his kids grew up. He’s just a "math guy." If the math says it’s too expensive to stay, he leaves. He views states like products. If the product is too expensive and the service is bad, he cancels the subscription.
He also hasn't "retired" to Florida. Far from it. He’s using Miami as a base of operations for his various "Tax Hive" ventures and his investments in the Middle East. It’s a strategic pivot, not a vacation.
Actionable Insights for Your Own Move
If you're looking at O’Leary’s move and thinking about doing the same, here’s what you actually need to know:
- Do the Math on Total Cost: Don't just look at the 0% income tax. Factor in the massive spike in home insurance and property taxes. In some cases, you might actually end up paying more if your income isn't in the "shark" bracket.
- The 183-Day Rule is Strict: If you keep a home in a high-tax state like New York or Mass, they will track your cell phone pings and credit card swipes to prove you weren't actually in Florida. You have to truly commit to the move.
- Update Your Legal Documents: Like O’Leary did in his court filings, you need to update your "domicile." This means changing your driver’s license, registering to vote in Florida, and moving your primary bank accounts.
Does Kevin O’Leary live in Florida? Yes. He’s a Miami Beach resident who traded the "Taxachusetts" headache for the Sunshine State's business-friendly climate. He’s officially a Florida man, though he’s probably the only "Florida man" with a collection of $100,000 watches and a permanent seat on a television set.
If you’re planning to follow his lead, start by auditing your current state tax liability versus the cost of Florida’s skyrocketing insurance premiums. Sometimes the "math" works, and sometimes you're better off staying put.