When you’re thinking about selling your ranch, let me tell you—the first thing you need to think about is taxes and financial planning. And yes, I know that sounds about as fun as fixing a busted fence in the middle of an Oregon rainstorm, but trust me, this is important. Especially if you’ve got one of those ranches that’s been in the family for generations, a Century Farm. I say this because multi-generational ranch and farm families tend to overlook this part—probably because no one wants to spend more time with their accountant than they already have to. But here’s the thing: if you don’t get your tax planning straight, you’re going to end up paying Uncle Sam more than you should, and let’s face it—he’s already getting plenty of your money.
Now, if you’re one of those newer ranch owners—you know, the folks who bought a ranch in the last 20 years or so as a weekend escape in Central Oregon or a cozy family retreat near Mt. Hood—you probably already have a team of tax and financial advisors telling you exactly how to keep your money where it belongs (hint: not in the IRS’s pockets). But for those of you who’ve been ranching in places like the Willamette Valley since your great-great-grandpa’s time, you might be thinking, “I’ll get around to it.” Well, here’s a little heads-up: if you don’t do it soon, you’ll be getting around to it with a whole lot less money in your bank account. You don’t want to be caught scrambling at the last minute, trying to figure out how to avoid Uncle Sam’s tax bite just as you’re putting that “For Sale” sign up.
While we’re at it, let’s talk about family. If you’re selling a multi-generational farm or ranch, this is where things can get tricky—more so than herding cats. Family dynamics are like land taxes: complicated and sometimes downright frustrating. There’s a particular kind of irony here—families that have stuck together on the same piece of land for generations can often find that selling the land is the thing that tears them apart. You’ve got to be careful with this part because the last thing you want is a family feud breaking out right when you’re supposed to be planning your exit.
Here’s a scenario that plays out more often than you’d think: four grown kids. One stayed on the ranch, maybe it’s out in Central Oregon or up near Silverton. They’ve been working that land for 30 years—blood, sweat, and calloused hands. The other three? They took off after high school for Seattle, Santa Cruz, or Portland, living lives that have nothing to do with the family farm. Now the parents pass on, and suddenly the three city-slickers want to sell the property. They’re ready to cash out. But that sibling who stayed behind, putting in all those years of hard work? They’re not so eager to see the land sold off, and who can blame them? They’ve got sweat equity invested, and maybe even a kid of their own hoping to keep the ranch alive.
It’s a tough spot. They’ve built their life around that ranch, while the others may only see dollar signs. Selling feels like ripping up roots that have been in the ground for generations—roots that go deeper than just the value of the land. So, what do you do when your family’s at odds? Well, if I had an easy answer, I’d be writing this from a beachfront home on the Oregon Coast. The reality is, there’s no magic fix. But here’s my best advice: talk. Start those conversations before the decision to sell is looming over you. Get everyone on the same page before emotions start running wild. Involve an expert to help talk through how to best proceed.
And remember, no matter how heated things get, there’s nothing more important than family. Except, of course, for making sure you’re not paying the IRS more than you have to—that’s important too. After all, you don’t want to end up like that guy down in the Willamette Valley who thought “capital gains” had something to do with Portland real estate and wound up handing half his ranch over to Uncle Sam. Keep it in the family, or at least, keep it out of the tax man’s hands!
We have walked through this process with many families and are here to help.
Reach out to get your real estate questions answered.
Suzanne Scott, Realtor