Selling a longtime home isn’t just about putting a “For Sale” sign in the yard—it’s about honoring the life that’s been lived inside and thoughtfully planning for what comes next. Whether you’ve lived in your home for 10 years or 50, this type of move comes with layers of decisions, emotions, and logistics.

At Dovetail, we believe in replacing overwhelm with ease—and that begins with planning.

Why Planning Is the Key to a Smooth Transition

A well-thought-out plan gives you confidence, clarity, and control. When you take the time to look at the big picture before jumping into the details, everything else falls into place more smoothly. Here's where we recommend starting:

1. Know Where You're Going First

One of the biggest mistakes we see is homeowners listing their house before having a solid plan for their next chapter. Are you downsizing to a condo? Moving in with family? Exploring senior living? Gaining clarity on your destination first helps shape your timeline, your needs, and the support you'll want around you.

2. Get Your Legal and Financial Ducks in a Row

Before you sell, make sure your legal and financial planning is up to date. This includes:

• Knowing if your home is held in a trust

• Clarifying ownership if others are on the deed

• Having power of attorney and healthcare proxy documents in place

• Speaking with your financial advisor and CPA about potential tax implications

It’s never too early to loop in your trusted professionals—or if you don’t have someone, we’re happy to introduce you to experts who specialize in this stage of life.

3. Explore Flexible Financial Options

Not everyone realizes that there are financial tools designed to support transitions like yours. You may qualify for solutions such as:

• Bridge loans that allow you to move first and sell later

• HELOCs (Home Equity Lines of Credit) to cover short-term costs

• HECMs (Home Equity Conversion Mortgages) if you're over age 62

Understanding your options can free up time and energy—and reduce pressure—when it matters most.

4. Embrace a “Plan A, B, and C” Approach

Nobody has a crystal ball. What works now might not work 5 or 10 years from now, and that’s okay. Creating flexible plans that evolve with your needs is smart, empowering, and ensures that your future care and lifestyle remain your choice.

5. Take a Breath Before You Leap

When homeowners feel rushed—whether by family, professionals, or life circumstances—it often leads to regret. We believe your transition deserves time, respect, and support. Pausing to plan is not a delay; it’s a gift to yourself and your loved ones.

Start with Confidence

If you’re feeling unsure about where to begin, you’re not alone. That’s exactly why we created our complimentary on-demand webinar:

“How to Sell Your Longtime Home for Top Dollar with Ease”

It’s designed specifically for older adults and their families, and walks you through the four most important parts of a smooth home sale:
✔️ Planning
✔️ Preparation
✔️ Pricing
✔️ Partnership

You can watch it anytime, from anywhere.
👉 Watch our Free Selling with Ease Webinar Here! and take the first step with ease.

Have questions or want to talk it through? Our team is here to help.
📧 Email: [email protected]
📞 Phone: 617-227-1600

Let’s make this next chapter one filled with confidence, calm, and clarity.