There’s a moment in almost every homeowner’s life when you look around your kitchen, your bathroom, or your dated 90s living room and ask the inevitable question: Should I renovate, or should I just sell?
It’s a fair question. Renovations are expensive, selling is exhausting, and Portland buyers? They’re picky. But here’s the truth I’ve learned after years of walking clients through both paths: the right answer usually has less to do with money and more to do with time.
If you’re about to pour $100K into a remodel, it has to buy you more than a prettier house. It has to buy you another decade in that house. Because a renovation never pays off immediately. You’ll enjoy it long before it shows up in your resale price, and that’s okay. In fact, that’s how it’s supposed to work.
If you’re adding square footage or taking on a big project, think long-term. Those kinds of investments only make sense if they’ll keep you happy in that home for at least another ten years.
When Renovating Makes More Sense Than Moving
When someone asks me whether they should stay or go, my first question back is: “If you sold right now, could you actually afford to buy what you want in your same neighborhood?” If the answer is no, and for many Portlanders it is, then staying put and reimagining what you already have starts to sound a lot smarter.
Portland’s market has shifted in ways that make trading up trickier than it used to be. You might sell for a strong number, but buying back into the same neighborhood at the next level is a lot harder than people realize. I’ve seen plenty of homeowners fall back in love with their homes after opening up a wall, redoing a kitchen, or turning a tired backyard into something lush and livable.
If you’re nodding along thinking, yeah, but I don’t want to live through construction, I get it. Renovations are stressful. But so is moving twice in a year because you bought a “temporary” house that didn’t actually fit your life. Sometimes the better move is to stay put and make it work better.
What’s Actually Worth Doing (and What’s Not)
Let’s talk about the Portland market for a second. I wish buyers were lining up to take on fixer-uppers again, but most of them aren’t. The pandemic changed everything. People spent too much time at home, and now they want kitchens and bathrooms that are finished and functional.
If you want a clearer sense of what really matters to buyers right now, read 5 Things Buyers Are Actually Paying For. It’s a quick gut-check on where to invest before you list, and a reminder that it’s often the simple, move-in-ready details that make the biggest impact.
If you’re thinking about selling soon, focus on what photographs well: fresh paint, good lighting, simple landscaping, and clean floors. You’d be amazed at what those few things can do. And resist the urge to go big on renovations right before listing.
But if you’re planning to stay a while, then yes, go ahead and tackle that kitchen. Just don’t expect to see an immediate dollar-for-dollar return. The payoff comes years down the road when you sell, and in the meantime, you get to actually enjoy it.
When I redid my own kitchen, it cost me around $75,000. Do I think I could list my house for exactly $75K more today? Probably not. But my lifestyle ROI? Off the charts. I cook more, I host more, I’m happier being home. And that counts for something.
Over-Improving (And Why It Happens More Than You Think)
This one’s tough because it usually comes from a place of love. When you’ve lived somewhere for a long time, it’s natural to want to leave it better than you found it. People love their homes, and they want to do right by them.
Every year, I meet homeowners who have poured tens of thousands into the invisible stuff: strapping foundations, upgrading insulation, fixing electrical systems. All good things! But when it’s time to sell, buyers don’t see that. What they see are the photos, the paint, the lighting, the vibe.
When I walk into a fixer someone’s lived in for years, I’m always checking the envelope first: roof, gutters, and downspouts. Deferred maintenance there can undo everything else. Those fixes matter deeply, but they rarely sell a home on their own.
You can’t price a house $70K higher just because you spent $70K under the hood. It’s not fair, but it’s true. Those upgrades make your home sound, not instantly Instagram-worthy, sellable. If you’re doing them for your own peace of mind, amazing. But if you’re doing them for ROI, pair them with the cute stuff.
There’s a reason I always say Buy Ugly, Sell Cute. The “sell cute” part matters just as much.
When Small Changes Lead to Big Returns
A few summers ago, I had clients, let’s call them M & F, who were ready to move to a small farm outside the city. They’d always planned to redo their kitchen “someday,” but suddenly “someday” became “next month.”
We kept it simple: new counters, backsplash, and painted cabinets. About $15,000 total. The house sold for $45,000 over asking, right in the middle of summer, which is normally one of the toughest times to sell.
That’s what strategy looks like in real life: small, focused investments that speak directly to what buyers care about most. If you’re mapping out the “cute but strategic” updates that actually move the needle before listing, start with the philosophy behind Buy Ugly, Sell Cute and layer in smart, cosmetic upgrades that photograph beautifully—and most importantly, talk to me first.
Lifestyle ROI: The Renovations That Pay in Happiness
Not everything has to be strategic. Some improvements pay off in joy, not equity, and honestly, those are my favorites. One of my clients recently spent a small fortune landscaping their backyard. They called me worried they were “over-investing.” I told them what I’ll tell you: the peace you feel walking into a backyard that feels like a sanctuary is priceless.
In gardening, there’s a saying: first year sleep, second year creep, third year leap. Do it early and give yourself time to enjoy the leap. It’s the same reason I tell people to do their kitchen early. You’ll never regret improving the spaces you actually live in every day.
The Bottom Line: Do It Early, Do It Right, and Do It for You
If I could give Portland homeowners one piece of advice, it’s this: don’t wait until you’re ready to sell to make your house the place you love. The amount of times I’ve helped sellers get their homes ready for the market—only to hear them say they’re heartbroken it finally looks the way they always wanted it to—is countless.
The best renovations are the ones you get to live in for a while. They add value in two ways: first, to your daily life, and then to your resale value years down the road. And if you’re ever torn between “worth it” and “not worth it,” ask yourself this: Would I still do this if I knew I had to stay here ten more years? If the answer is yes, it’s probably the right move.
Thinking about renovating before you sell? Let’s talk strategy. Whether you’re deciding what to upgrade, when to do it, or how to make the most of your investment, we can help you find the sweet spot between lifestyle and return. Get in touch here.
