Retiring to Florida: the money moves that matter.

Every year, thousands of families move to Florida with retirement in mind, and most of them capture only a fraction of what the move is worth. The state’s advantages are genuine — no income tax, no estate tax, homestead protection that has sheltered family homes for a century. But almost all of the money is in the sequencing: what you sell before the move versus after it, when your domicile genuinely changes, and what you do in the narrow window between leaving your old state and starting required distributions.

The one decision worth the most: sell before, or sell after

Gains on intangible assets — company stock, a business interest, a concentrated position — are generally taxed by the state you live in when you recognize the gain. A New Jersey resident selling a $4M position pays New Jersey on it; the same person, selling six months later as a genuine Florida resident, may pay no state tax at all. On a large sale, the difference between those two sentences can exceed the price of the house you are moving into. Estimate your own number with our Florida calculator — and if a sale is anywhere on your horizon, get the sequencing decision made before you list the business or exercise the shares. We wrote the full sequencing analysis — which order works, which deal structures a move cannot save — in sell the business first, or move first?

Residency is a fact pattern, not a checkbox

High-tax states do not let seven-figure taxpayers leave quietly. New York and its peers audit departures, and they win when the move was paperwork rather than reality. What survives an audit is a genuine change of domicile, documented: the declaration, the homestead filing, the driver’s license, the voter registration, the doctors, and a calendar that shows your life actually happening here. Our residency checklist walks the full list in order — it is the same one we work through with clients.

The window almost everyone wastes

The years between retirement and required minimum distributions are often the lowest-income years of your adult life — and for a new Florida resident they are doubly valuable, because Roth conversions in those years pay no state tax at all. The same window interacts with Medicare’s IRMAA surcharges, which look back two years at your income: converting carelessly can push a couple into brackets that cost thousands per year, while converting deliberately can lower every RMD you will ever take. This is a modelling problem — year by year, in writing — not a rule of thumb.

What does not move with you

Two honest cautions. Your trust does not become a Florida trust because you did — trusts have their own state ties, and documents drafted for New York or Illinois law deserve a Florida review. And your estate documents, powers of attorney, and health directives should be redone under Florida law once you are here; out-of-state documents are honored unevenly at exactly the moments that matter most.