Is Now Really the Right Time to Sell? (Especially for Longtime Homeowners)

A Perspective for Senior Living Sales Teams

There’s no shortage of opinions out there. Rates are up. Inventory is tight. Prices are holding… or maybe slipping? It’s a mixed bag.

And yet, you keep hearing:
“Now is a great time to sell!”

But is it really?
The real answer is: It depends. And it’s not just about the market — it’s about the person.

As Sales Counselors, it is our job to help guide our customers through this conversation. It’s important to keep in mind that 99% of our customers have never made this decision, and as a sales counselor, you have a great deal of experience to share. It’s up to us to set the expectation on what the next step should be. Here are some ideas for further exploration to help drive this decision.

It’s Not Just About Timing — It’s About Fit

For those who’ve been in their home for decades, the best question is: “Does this home still fit your life?”

If it’s feeling too big, too quiet, or just too much to manage — that might be a sign. As a sales counselor, your job is to help them see that selling can be a smart and empowering next step, not just a reaction to market headlines. If your customer is worried about what they are hearing in the news, gently remind them that the news is paid to keep their attention and drive emotions, and it’s certainly OK to take a break!

Why People Are Making the Move

Here’s what many older adults are thinking about right now:

• They’ve built up strong equity.

• Serious buyers are still in the market.

• Low inventory means their home could stand out.

• But most importantly: Life changes are driving the decision — not just market trends.

Whether it’s health, family, or just wanting less to manage, the motivation to move often comes from within — not outside forces.

So… Where Do They Go?

That’s the question they may not be asking out loud — but it’s the one you can help answer. Here’s how to guide the conversation toward what’s possible:

• Downsizing = Right-sizing: Smaller space, simpler life. “Right now in your home, how long does it take you to locate important documents, the ‘good’ scissors, and basic tools? Is the clutter in your home overwhelming?” Most people worry that downsizing means getting rid of everything when truly, this is an opportunity to get organized and simplify life. Another good question to ask is about control – “How much control do you want to have over your belongings?”

• Community = Belonging: Wellness, dining, activities — all in one place. “In your current home, how often are you running into neighbors and having meaningful connections – not just a pass by on the street, but long talks over coffee, or spending time together doing a puzzle or game?” 

• Predictable costs: Especially with LifeCare or CCRC models. Something to ask your prospect – “What budget have you put together for long-term care costs? What is your familiarity with the monthly costs?”

• Peace of mind: Support is there if/when they need it. “How much do you value having a plan in place?”  

• Closer to what matters: Grandkids, healthcare, connection. “How have you considered how close you want to be with your loved ones? Who are some of those important people in your life?”

You’re not just helping them let go of a house — you’re helping them envision a better lifestyle.

Coaching Tip: Be Their Guide, Not Just the Salesperson

You're not just offering a floor plan or amenities — you’re helping someone through a major life decision. That takes trust, empathy, and clarity.

Here’s how to keep your approach grounded and effective:

1. Start with Discovery

Don’t start with a sales pitch. Make a connection by showing interest in their life, and then ask questions that uncover life goals:

• “What’s changed about your home lately?”

• “What would make life easier or more enjoyable right now?”

• “If your home could take care of you, what would it be doing?”

2. Know the Market, But Keep It Human

Yes, values are strong — but don’t oversell. Keep the focus on what the move unlocks, not what they’re giving up.

3. Be a Trusted Resource

Offer connections to trusted real estate agents, downsizing specialists, or movers. Even small gestures build big confidence.

4. Reframe the Timing

It’s not about market highs. Ask: “Is your home still serving your goals?”
If not — that’s the right time.

Final Thought: Help Them Move Forward

Markets will rise and fall. That’s just what they do.
But life keeps moving — and it doesn’t wait for perfect conditions.

When someone is thinking about selling, help them see what’s on the other side:
Less stress, more support, more freedom, and a lifestyle that aligns with who they are now. It’s not just a sale. It’s a new chapter, and you get to be the one who helps open the door.