Florida has no state income tax, so no state capital gains tax. But the federal rate (up to 20%) and the 3.8% NIIT still apply, and on a big sale that's a serious bill. Here's how to defer the federal bite.
A plain-English guide for sellers: how a structured installment sale defers the tax when you sell a business, practice, or property — the math, the alternatives, and how to know if your deal fits.
Drop your info — instant PDF download + within 1 business day Hans will email a preliminary read on which structure fits your deal. No retainer. Carrier compensates the broker — not you.
📞 Hans Goldstein · 213-290-4977 · CA Insurance License #4322192 · Independent §453 specialist · Goldstein & Co. LLC
Florida's tax appeal is real: no state income tax means no state capital gains tax. It's why so many high-net-worth sellers and retirees are here. But the federal capital gains tax (up to 20%) and the 3.8% Net Investment Income Tax don't care where you live, and on a large sale, that federal hit is still the biggest check most people ever write.
Between booming real estate, business sales, and retirees unwinding decades of appreciated investments, Florida sellers regularly face seven-figure gains. No state tax helps, but recognizing the whole federal gain in one year still maxes out the 20% bracket and triggers the 3.8% surtax, and can spike Medicare IRMAA premiums for retirees.
A §453 structured installment sale spreads the proceeds, and the federal gain, over future years, keeping more in the 15% bracket, reducing the 3.8% NIIT, and (for retirees) helping avoid the IRMAA cliff. Payments are carrier-backed and guaranteed. Works for property, a business, or stock; no replacement property needed, unlike a 1031.
Florida saves the state tax, but the federal tax on a large sale is still substantial, and for retirees it can quietly raise your Medicare costs. Estimate it on the calculator (select Florida) and plan before you sell.
No. Florida has no state income tax, so there is no state capital gains tax. You still owe federal capital gains tax (up to 20%) and the 3.8% Net Investment Income Tax on a sale.
No state tax, but federally up to 20% plus the 3.8% NIIT, roughly a quarter of a large gain in the year of sale, with depreciation recapture taxed on top for property.
Yes. A §453 structured installment sale spreads the federal gain over several years, keeping more in the 15% bracket and reducing the 3.8% surtax, and for retirees, helping avoid an IRMAA Medicare premium spike.
It can. A large one-year gain raises your modified income, which can push Medicare IRMAA premiums higher two years later. Spreading the gain with a structured installment sale keeps annual income lower and can avoid that.
Use the free calculator and select Florida (it applies $0 state tax); it estimates your federal capital gains, NIIT, and recapture, plus the savings from deferring.
Before you sign anything, run your numbers with someone who structures the deal to be tax-smart and audit-ready from day one.
Call 213-340-2018 Run the Numbers →