Was His Home Connecticut or Florida? The Difference Is a $13 Million Tax Bill

August 8, 2026 - 10:19

One family's estate is at the center of a growing fight over how states tax the wealthy who own homes in more than one place. The dispute hinges on a simple question: was the late businessman's primary residence in Connecticut or Florida? The answer changes the tax bill by roughly $13 million.

Connecticut says the man was a resident and owes taxes on his worldwide income. Florida, which has no state income tax, says he was a Sunshine State resident, and his estate should not pay Connecticut a dime. The case is now in court, and it is drawing attention from tax lawyers and financial planners across the country.

The core issue is that states are getting more aggressive about chasing tax money from people who split time between high-tax and low-tax states. Connecticut has a strict set of rules for what makes someone a resident, including how many days they spend in the state and where they keep their driver's license, voter registration, and even their doctor. The estate argues that the man had truly moved to Florida, with a permanent home there, and only visited Connecticut for business and family.

But Connecticut officials point to evidence they say shows he never really left. They cite his continued use of a Connecticut home, his involvement in local charities, and the fact that his spouse spent significant time there. The estate counters that those visits were temporary and that his life was centered in Florida.

The outcome could set a precedent for other wealthy families. If Connecticut wins, it may encourage other high-tax states to dig deeper into the lives of part-time residents. If the estate wins, it could give more cover to people who want to establish residency in a tax-friendly state while keeping ties to their old one.

For now, the case is a reminder that where you call home is not just a matter of feeling. It is a matter of paperwork, proof, and, sometimes, a very large check. The estate has said it will fight the bill all the way, and both sides are preparing for a long legal battle.