9 Most Overlooked Tax Breaks for Retirees: Kiplinger

2. Deduct Medicare Premiums

If you become self-employed after you leave your job, you can deduct the premiums you pay for Medicare Part B and Part D, plus the cost of supplemental Medicare (medigap) policies or the cost of a Medicare Advantage plan.

One caveat: You can’t claim this deduction if you are eligible to be covered under an employer-subsidized health plan. (Photo: Shutterstock)

3. Spousal IRA Contribution

Generally, you must have earned income to contribute to an IRA, but if you’re married and your spouse is still working, he or she can contribute up to $7,000 a year to an IRA that you own (assuming you’re at least 50 years old).

For this year only, you also have more time to make contributions to an IRA for 2019. Normally, the due date for 2019 IRA contributions would have been April 1, but due to COVID-19, the deadline has been extended until July 15.
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7. Timing.

Twenty percent of beneficiaries began thinking about their Medicare options after becoming eligible or turning 65, while 42% nearing eligibility had not started thinking about their Medicare options.

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5. Avoid the Pension-Payout Trap

If you get a lump-sum payment or other rollover distribution from a company plan, you could fall into a pension-payout trap.

If you take such a distribution, the company is required by law to withhold a flat 20% for the IRS, even if you simply plan to roll over the money into an IRA. Moreover, even if you complete the rollover within 60 days, the IRS will still hold onto the 20% until you file a tax return for the year and demand a refund.

Not to panic: There’s a way around such an outcome. Simply ask your employer to send the money directly to a rollover IRA. As long as the check is made out to your IRA and not to you personally, there’s no withholding.
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6. The RMD Workaround

Required minimum distributions are not required in 2020, again because of the pandemic. However, retirees taking RMDs from their traditional IRAs in other years may have an extra option for meeting the pay-as-you-go demand.

If you don’t need the required distribution to live on during the year, wait until December to take the money. And ask your IRA sponsor to hold back a big chunk of it for the IRS, enough to cover your estimated tax on both the RMD and your other taxable income as well.

Although estimated tax payments are considered made when you send the checks, amounts withheld from IRA distributions are considered paid throughout the year, even if they are made in a lump sum at year-end. So, if your RMD is more than big enough to cover your tax bill, you can keep your cash safely ensconced in its tax shelter most of the year and still avoid the underpayment penalty.
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7. Give Money to Your Family

Few Americans have to worry about the federal estate tax as most have a credit large enough to permit them to pass up to $11.58 million to heirs in 2020. Married couples can pass on double that amount.

But, if the estate tax might be in your future, be sure to take advantage of the annual gift tax exclusion, which lets you give up to $15,000 annually to any number of people without worrying about the gift tax. Your spouse can also give $15,000 to the same person, making the tax-free gift $30,000.
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2. Keep the timing of when gift checks are cashed in mind. Pay close attention to when a gift paid by check is cashed. A gift made to an individual this way is deemed complete in the year it is paid, certified and accepted by the drawee’s bank, not when written, Doyle says. However, when gifting to a charitable organization, be sure to write the check by the end of this year, he adds. Even if it’s cashed within "a reasonable amount of time" after the start of 2021, it's still deductible for income tax purposes in 2020. (Photo: Shutterstock)

9. Tax-Free Profit From a Vacation Home

To qualify for tax-free profit from the sale of a home, the home must be a principal residence and you must have owned and lived in it for at least two of the five years leading up to the sale. But you can capture tax-free profit from the sale of a former vacation home.

Say you sell the family homestead and cash in on the break that makes up to $250,000 in profit tax-free ($500,000 if you're married and file jointly). You then move into a vacation home you’ve owned for 25 years. As long as you make that house your principal residence for at least two years, part of the profit on the sale will be tax free.
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