Opens in a new tab

Second home dream, tax nightmare

May 30, 2008

Throughout our married life, the hubby and I have harbored the dream of owning a second home.

Mountain_log_cabin_2When we were newlyweds living in Maryland just outside Washington, D.C., we frequently thought how nice it would be to have a cabin in the mountains of nearby West Virginia. The thought of one day making cool weekend getaways from the heat and humidity of the nation’s capital kept us going every sweaty summer.

Never happened.

For years, also while still in suburban D.C., we would vacation in the Sunshine State to escape the last of the MidAtlantic winter season. And after each of those February or March trips, we swore we were going to buy a condo on Sanibel Island so we could spend future winter breaks watching shorebirds from our own seashore balcony.

Never happened.

Then we moved to Florida. This is it, we told each other. The perfect time for that second home.

We were on the Atlantic Coast, but would buy a place just across the state, about a three hour drive, letting us occasionally look at a different beach from the comfort of our own condo.

Florida_beach
Even better, we’d be able to see the sun set in the Gulf of Mexico, much preferable for our night-owl ways, rather than getting up way early to see the sun rise from the Atlantic, as was the option (rarely chosen, I must confess) at our main home.

And since we were already in Florida, we assured ourselves, we’d actually use the property more, thereby making such a second-home purchase now a much smarter move than all our prior property pipe dreams.

You guessed it. Never happened.

Now we’re in Central Texas. And with summer temps that regularly walk the triple digit degree line, we now discuss buying — and even send off for real estate brochures about — vacation homes on the Texas Gulf Coast or cabins in the mountains of New Mexico.

Yeah, we know. It’s never gonna happen. But everybody needs a dream.

Second home nightmares: Some folks, whose stories are related in today’s New York Times, would have been well-advised to keep their second homes as mere dreams, too.

In Lose Homes, Pay More Tax, Times reporter Jonathan Glater explores the growing number of second property foreclosures and the huge tax bills produced by many of the soured real estate deals. I previously blogged about this, albeit for primary homes, in Foreclosure’s costly tax implications.

"Some of the biggest losers in the real estate slump are not purchasers of mansions they could not afford," writes Glater. "They are buyers of second homes — or third ones, for that matter — who are sitting on a tax time bomb."

Some of these home buyers, continues Glater, "will lose their properties in foreclosure and then stagger into bankruptcy under the weight of a sizable tax bill."

The reason: The foreclosure debt relief law enacted late last year (and blogged about here) only protects taxes due on forgiven debt related to a taxpayer’s principal residence, not a vacation home or investment property.

And the consensus is that’s how it should be.

We, and I’m talking about us as individual citizens and our lawmakers, have long embraced using tax laws to reward homeownership. That means that most of the tax benefits go toward the homes we actually live in, the American dream and all that, although it’s debatable as to whether that should be the case, as I blogged about in When renting is the right choice.

Folks who plan well enough financially or are lucky enough to own multiple properties, good for them.

But when things go bad for these wannabe real estate magnates, I don’t want my tax money helping owners of multiple homes (and their lenders) pick up the pieces. I have plenty of ways to spend that cash on keeping up my lone home, thank you.

And I certainly don’t want to rescue owners of additional properties who, as a bankruptcy lawyer quoted in the Times story says, were simply "buying properties to become mini-Donald Trumps." (I am now trying to blind my mind’s eye, which unfortunately has latched onto that visual!)

Many buyers, the article also notes, bought multiple properties "with the hope of selling them for a quick profit." Others, says another bankruptcy attorney, "seem to have thought that if they did not borrow against these [second] homes, they were wasting equity."

To those folks, I say you pay your money, you take your chances. Leave my tax money alone. I might one day need some of it to pay the property tax bill on my own second home!

Share:

The More Tax Posts tab at the top of this page will take you to, well, more tax posts. You also can search below for a tax topic. 

Latest Posts
confused office worker
8 workplace benefits questions to ask this enrollment season

October 26, 2026

Millions of U.S. workers are now deciding what workplace benefits, some of which also offer…

Read More
TAX-SAVVY WAYS 
TO WRAP UP 2026

It’s over! With October’s extended filing deadline behind us, it is now time to focus on year-end moves to reduce your 2026 tax bill. 

You’ll find ways to do just that on the Tax Tips page (see the More Tax Posts drop-down menu at the top of the blog), as well as the separate tax tip pages for each month, notably October through December. If you’re on the Tax Tips page, you’ll find a monthly list at the end of this column. If you’re on another blog page, you can head straight to the October tips; at the bottom of that tips page you’ll find links to all the other 11 months’ collections of tax advice.

Not to spoil what you’ll find in that tax advice, but it does cover such things as tax deductions for charitable donations, investment moves that could reduce tax due, and ways to max out your tax-favored retirement savings. 

Finally, as the year winds down, things get hectic. There are lots of other things to occupy our time, like the much more fun upcoming holidays. But don’t lose sight of taxes, since timing is key. To be of use, most tax moves must be made by the end of the tax year. That’s Thursday, Dec. 31, which also is the last business day of the year. 

So that you don’t miss that final tax year deadline, also keep an eye on the countdown clock below. It will keep you on top of just how much time is left to make important, tax-saving moves. (Note: I’m in the Central Time Zone, so adjust accordingly for where you live.)

Comments
  • I also don’t think our tax dollars should help those whose primary home is in jeopardy. Capitalism is the best economic system on the planet, but it does not guarantee success. You are rewarded for making efficient use of capital. Inefficient use leads to losses; it should be that way whether it is a second home or primary home.
    I feel for those who lose a home due to a disability or health problem, but outside that I don’t have much sympathy. Even those who got snookered into a bad mortgage shouldn’t get a break. Do some research.
    Anyway, I wish you could have gotten your vacation home. They can work out if people plan for it.

Leave your comment