3 Weird Regrets You Might Feel After Moving Out of Your House

By Cathie Ericson
Jan 2, 2018
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I was one of those lucky kids who lived in the same house throughout my childhood, in Orange County, CA, where kids played whiffle ball after dinner and rode their bikes to soccer practice. Throughout college and my 20s, I returned here during summers and vacations because, even though I’d moved on, it still felt like “home.”

Then the day arrived when my family sold the place, as happens with most childhood homes. Yet even after it belonged to someone else, I harbored such fond memories that when I flew in for a 20th-year high school reunion, I decided to drive by and check it out.

As I pulled up to my old address, I eagerly awaited a sweet blast of nostalgia. Had the new owners kept the lawn lush where I used to practice my cartwheels? Would some new pack of kids be out there playing whiffle ball?

Yet once I spotted my old home, my excitement turned to dread. Because everything looked the same—as in, exactly the same, just older and woefully neglected. The garage door that I used to hit tennis balls against was the same, swinging out to open, instead of rising up. Yep, that’s how old it is. The picket fence that was once covered with roses was bare. The paint on the house was peeling so much, I could see the wood underneath.

It was just depressing. I kept right on driving.

And what was even more distressing was the fact that, according to realtor.com®, the home had increased in value by nearly 50% over the past nine years. If only my family had held onto the property a little longer, we could have been hundreds of thousands of dollars richer!

My family is hardly alone in this angst, a sentiment commonly echoed among home sellers who moved out two months or 20 years earlier.

“It’s natural to be curious about what happens to your old home, since these residences are filled with milestones and memories of friends and family,” says Allison Bethell, a real estate analyst for FitSmallBusiness.com.

Yet therein lies the rub: Changes to a former home or neighborhood—or lack thereof—can hit you emotionally in ways you might not anticipate. Just so you’re prepared for what’s in store if you do “check in” on your old home, here are some weird realizations and regrets that might get you kicking yourself.

1. You’ll be horrified if it looks run-down

Dylan Diersen, a real estate agent with First Weber, grew up as a military kid, moving to a new house every few years with his family. Whenever he happened to be in a town where he used to live, he’d usually do a drive-by, the same way I did. That is, until he realized that it was typically disappointing.

“We almost always purchased fixer-uppers and put a ton of work into them,” he says. Yet once the house was handed over to someone else, the new owners rarely kept up the maintenance. “Seeing how the new owners don’t take care of a home as well as we did kills the soul a little bit,” he says.

2. You’ll be horrified if it looks fixed up

Yet for every tale of a house being neglected, there are 10 more of houses where current owners dismantled beloved features from the past.

“I was sad when we discovered that the new buyer destroyed the stone wall that my husband and I built around the garden,” says Ali Wenzke of Chicago. “We had carted hundreds if not thousands of pounds of concrete blocks from the home improvement store. It was built with blood, sweat, and tears. And now it’s gone!”

Thomas Bayles, a homeowner and house flipper in Los Angeles, knows all too well what happens when you hand the keys to the next owner who may not share your taste.

“I spent five months renovating a home to flip; the landscaping alone cost me about $15,000 and a few sleepless nights deciding on the design,” Bayles says. The new owner promptly demoed the front yard and spent what Bayles estimates to be about $20,000 on a completely different look.

“This is when I realized that beauty truly is in the eye of the beholder,” he says.

3. You’ll be horrified if the price has skyrocketed

Changes to the home are bad enough, but if the home’s price has skyrocketed, that’s a whole different kind of pain.

Case in point: The first property Bayles ever bought was a duplex for a little over $500,000. He took his time restoring the property and sold it a year later for just over $800,000. Which is great, right?

“A mere three years later, that property was worth approximately $1.2 million,” he says. “I kick myself all the time for leaving $400,000 on the table.”

And price appreciation can happen quickly, too. After moving in April, Jessica Landon watched her previous home in a suburb of Portland, OR, gain $20,000 in value over a matter of six months.

“It’s hard not to say to yourself, ‘If I’d waited six more months I could have made $20,000 more,’” says Landon. “At some point, I had to stop looking or I knew I’d drive myself crazy.”

How to avoid home-selling regrets

Checking out a home you once lived in is a lot like checking up on your exes on Facebook: Sometimes, it’s best just to not go there.

“Don’t Monday morning quarterback yourself,” says Realtor® Shannon Aronson of Keller Williams in Summit, NJ. For instance, if you’re kicking yourself for not holding onto a place longer to make more money, tell yourself that odds are, you moved when you had to—and that the home could have just as easily plummeted in price.

And while a quick drive-by of your old home might be OK, you may want to refrain from knocking on the door to see the interior, or obsessively checking photos online. Because these are the facts: Once you’ve moved out, this home is no longer your home. You have a new place—why not focus on that instead?