9 Tax Mistakes Florida Retirees Keep Making in 2026

Think moving to Florida means your tax worries retire with you?

They don’t.

No state income tax is a gift, but the biggest retirement tax traps are federal, and they follow you to Naples, The Villages, and every cul-de-sac in between.

Most of these cost four figures, and almost nobody sees them coming.

Note: This is general information, not financial or tax advice. Tax rules and dollar amounts are subject to change, so confirm the current details with a professional.

1. Missing Your First RMD Deadline

A required minimum distribution (RMD) is the amount the Internal Revenue Service (IRS) makes you pull from a traditional IRA or 401(k) once you reach a certain age.

That age is 73.

Your first RMD carries a hidden trap because you can delay it until April 1 of the year after you turn 73.

Wait that long, and two withdrawals land in the same tax year, which can shove you into a higher bracket.

Skip a required withdrawal of about $18,900 on a $500,000 IRA, and the penalty on that missed amount runs 25%, close to $4,700.

Ouch.

Correct the mistake quickly, though, and the IRS drops that penalty to 10%.

2. Assuming Social Security Isn’t Taxed

Florida never touches your Social Security, but the IRS might.

It comes down to combined income, which is your adjusted gross income plus any tax-free interest plus half of your benefits.

Cross $25,000 as a single filer, and up to half of your benefits become taxable.

Pass $34,000, and up to 85% of them count as income.

Married couples hit those tiers at $32,000 and $44,000.

A couple pulling $50,000 from an IRA on top of $40,000 in benefits sails past $44,000, so the IRS taxes most of those benefits.

Those thresholds haven’t moved since the 1980s, so more retirees drift into them every year.

Every year.

3. Tripping the IRMAA Surcharge

IRMAA stands for income-related monthly adjustment amount, a surcharge Medicare adds to your Part B and Part D premiums when your income runs high.

The standard Part B premium in 2026 is $202.90 a month.

Cross $109,000 as a single filer or $218,000 as a couple, and that jumps to $284.10.

The trap is the timing, because Medicare looks at your modified adjusted gross income (MAGI) from two years back.

Your 2026 premium keys off your 2024 return.

Sell a house or take a big withdrawal in 2024, and your Medicare bill runs higher today, long after the money is gone.

Two years later.

4. Skipping the Homestead Exemption

The homestead exemption knocks up to $50,000 off the taxable value of your primary Florida home.

The first $25,000 covers every tax, including school taxes.

A second $25,000 applies to assessed value between $50,000 and $75,000, and it skips school taxes.

On a home assessed at $300,000, that exemption trims the taxable value to $250,000, which can save well over a thousand dollars a year.

The catch is the calendar.

You have to apply with your county property appraiser by March 1, or you wait a full year.

One deadline.

Many new arrivals from up north never file, and they overpay for it.

5. Leaving Portability on the Table

Save Our Homes caps how fast the taxable value of a homestead can rise, at 3% a year or the inflation rate, whichever is lower.

Stay put for years, and the gap between your home’s market value and its capped value grows into a hefty discount.

Portability lets you carry that discount to your next Florida home, up to $500,000 of it.

Say your market value is $400,000, but Save Our Homes held your assessed value at $250,000.

That $150,000 gap can follow you from Naples to Sarasota, so you don’t start over at full value.

Big deal.

You have three tax years to make the move, and you file for portability with your new county.

Retirees downsizing across the state skip this form all the time, and they hand the county money they could have kept.

6. Waiting Too Long on Roth Conversions

A Roth conversion moves money from a traditional IRA into a Roth IRA, and you pay tax on it now so it grows tax-free later.

The sweet spot is the gap between retiring and starting RMDs, when your income dips.

Convert during those lean years, and you fill up the low tax brackets on purpose.

Wait until RMDs and Social Security stack on top of each other, and every converted dollar costs more.

There's a bonus for 2026, too.

Retirees 65 and older can claim an extra $6,000 deduction through 2028, which softens the tax on a conversion done now.

Time it right.

Just remember a big conversion can raise your Medicare premium two years later, so don't overdo it in one year.

7. Fumbling Your Capital Gains

Sell a stock or a rental you've held over a year, and it's a long-term capital gain, taxed at a lower rate than regular income.

Here's what many retirees miss.

If your taxable income stays under $49,450 single or $98,900 married, your long-term gains face a 0% rate.

A couple with $80,000 in taxable income can realize $18,000 in long-term gains and still land under the line, paying zero federal tax on that profit.

Sell something you've owned under a year, though, and it's a short-term gain, taxed like a paycheck.

Timing matters.

One patient year can turn a taxable sale into a tax-free one.

8. Ignoring the QCD Shortcut

A qualified charitable distribution (QCD) sends money straight from your IRA to a charity, and it counts toward your RMD.

You have to be 70½ or older.

The money never shows up as taxable income, which beats taking the withdrawal and donating the cash afterward.

In 2026, you can give up to $111,000 this way.

Say you owe a $20,000 RMD and you already give $5,000 a year to your church.

Route that $5,000 as a QCD, and you knock it off your RMD and your taxable income at once.

Tax-free giving.

Lower income also means less Social Security taxed and a smaller IRMAA risk down the road.

9. Forgetting to Withhold

No employer means no one holds back taxes for you anymore.

Pensions, IRA withdrawals, and even your Social Security check can all have federal tax withheld, but only if you ask.

Skip it, and you owe the whole bill in April, plus a penalty.

Both sting.

The IRS charges an underpayment penalty when you haven't paid enough as the year goes.

You avoid it by covering at least 100% of last year's tax, or 110% when your income tops $150,000.