Delaying Medicare enrollment. What to know

Dear Liz: When my husband was approaching 65, he was employed and covered by a high deductible healthcare plan (HDHP) with a health savings account by his employer. Neither his employer nor our local Social Security office had concrete advice on how to proceed about enrolling in Medicare, but after tremendous research, he eventually delayed enrollment. Now I am approaching 65. My husband is still working, and I am still covered by his health insurance, although both are in his name. Do I enroll in Medicare at the appropriate time or do I delay enrollment like he did?

Answer: Delaying Medicare enrollment can result in penalties that can increase your premiums for life. If you or a spouse is still working for an employer with 20 or more employees, however, generally you can opt to keep the employer-provided health insurance and delay applying for Medicare without being penalized. If you lose the coverage or employment ends, you’ll have eight months to sign up before being penalized.

Delaying your Medicare enrollment also allows your husband to continue making contributions on your behalf to his health savings account. In 2025, the HSA contribution limit is $4,300 for self-only coverage and $8,550 for family coverage, plus a $1,000 catch-up contribution for account holders 55 and older. Once you enroll in Medicare, HSA contributions are no longer allowed.

Medicare itself suggests reaching out to the employer’s benefits department to confirm you are appropriately covered and can delay your application. Let’s hope that by now your employer’s human resources department has gotten up to speed on this important topic.

Dear Liz: We read your recent column about capital gains and home sales. Our understanding is that if you sell and then buy a property of equal or greater value within the 180-day window, the basis for tax purposes is the purchase price, plus the $500,000 exemption, plus the improvements to the property, minus the depreciation, whatever that number comes to, and then the profit above that has to be reinvested or it is subject to capital gains. We talked to our CPA about this and he referred us to a site that specializes in 1031 exchanges.

Answer: You’ve mashed together two different sets of tax laws.

Only the sale of your primary residence will qualify for the home sale exemption, which for a married couple can exempt as much as $500,000 of home sale profits from taxation. You must have owned and lived in the home at least two of the previous five years.

Meanwhile, 1031 exchanges allow you to defer capital gains on investment property, such as commercial or rental real estate, as long as you purchase a similar property within 180 days (and follow a bunch of other rules). The replacement property doesn’t have to be more expensive, but if it’s less expensive or has a smaller mortgage than the property you sell, you could owe capital gains taxes on the difference.

It is possible to use both tax laws on the same property, but not simultaneously.

In the past, you could do a 1031 exchange and then convert the rental property into a primary residence to claim the home sale exemption after two years. Current tax law requires waiting at least five years after a 1031 exchange before a home sale exemption can be taken.

You can turn your primary residence into a rental and after two years do a 1031 exchange, but you would be deferring capital gains, while the home sale exemption allows you to avoid them on up to $500,000 of home sale profits.

Liz Weston, Certified Financial Planner®, is a personal finance columnist. Questions may be sent to her at 3940 Laurel Canyon, No. 238, Studio City, CA 91604, or by using the “Contact” form at asklizweston.com.