Relocation Tax Comparison Tool

Should you move to a no-income-tax state in retirement? Maybe, but the income-tax headline is the smallest part of the answer. The real comparison stacks income tax, estate tax, and property tax across both states, and the winner often isn’t the one with the flashy zero on the income line.

Everyone fixates on the income-tax rate because it’s the easy number. For a retiree drawing down a portfolio in a high-tax state like New York, the annual income-tax saving from moving to Florida is real and worth counting. But two larger taxes hide behind it, and a move that wins on income tax can still lose on the full picture.

The decision this settles

This tool answers a comparison, not a single state’s bill. State A versus State B, across the taxes that actually move the needle for an affluent retiree. The point is to surface the taxes people skip, because the income-tax saving is usually the one they already see and the estate-tax saving is the one that quietly dwarfs it.

How the math works

Three taxes, compared side by side, then summed.

• Income tax. Your state’s rate applied to the income your plan generates each year. Retirement income, withdrawals, capital gains, the taxable slice of Social Security. New York taxes most of this; Florida taxes none of it. Worth knowing: New York fully exempts Social Security and government pensions and excludes a slice of private pension and IRA income, so the gap is narrower than the top rate suggests. See NY pension taxation.
• Estate tax. The big, overlooked one. New York levies its own estate tax with a brutal feature, the estate tax cliff: go a little over the exclusion and the entire estate becomes taxable, not just the excess. Florida has no estate tax.
• Property tax. Annual tax on your home, which can swing hard between a Westchester house and a Florida one of similar value.

Total tax difference = (income + estate + property tax in State A) − the same in State B, weighed over your real time horizon.

A worked example

Take a New York couple, $4M estate, $200,000 of annual taxable retirement income, considering Florida.

On income tax, say New York costs them roughly $12,000 a year more than Florida’s zero. Over a 25-year retirement, call it $300,000. A real number.

Now the estate tax. For 2026, New York’s estate tax exclusion is $7,350,000, so a $4M estate owes no New York estate tax today. The couple is under the line. But estates grow. If theirs compounds past that exclusion, the cliff means the whole estate gets taxed, not just the overage, and that can cost far more in one stroke than decades of income-tax savings. Florida removes that risk entirely.

The income-tax saving is visible and steady. The estate-tax exposure is lumpy, future, and potentially much larger. A comparison that stops at the income line sees a third of the story.

The part most people miss

Here’s the second-order trap: the tax saving only counts if the move is real. New York does not wave goodbye to high earners quietly. Keep a home, spend too many days in-state, or leave your doctors and your life there, and New York can argue you never changed domicile, then bill you for the income tax you thought you’d escaped, plus penalties. The saving you modeled evaporates if residency doesn’t hold up. Winning the comparison on paper and losing the residency fight is the worst of both worlds.

And the deeper cost isn’t even tax. It’s the life. Move for a tax saving and end up far from grandchildren and friends, and you’ve optimized the spreadsheet while paying a price the spreadsheet never showed. I’ve watched people let the tax tail wag the whole dog. The math should inform the move, never make it.

Run all three taxes, over your real horizon, and only then weigh the number against everything that isn’t on the tax return. That’s how you compare two states like an adult instead of chasing a zero.