🦃 5 Real Estate Conversations to Have With Your Family This Thanksgiving

By Katie Moore, Engel & Völkers Annapolis

Thanksgiving brings together the people who matter most- which also makes it the perfect time to talk about the plans, dreams, and decisions that shape your family’s future. And let’s be honest... between the turkey, the laughter, and the stories that come out every year, big conversations naturally find their way to the table.

Here are five meaningful, money-smart, future-focused real estate conversations you can have with your loved ones this Thanksgiving- the ones that can help every generation make confident decisions heading into the new year.

1. “Is it time for someone in the family to downsize?”

Empty nesters, aging parents, or family members who are tired of the maintenance of a big home often start feeling it around the holidays.
That extra space they once needed might now feel like work.

Discuss questions like:

• Does the current home still fit your lifestyle?

• Would a smaller home, condo, or waterfront retreat feel more freeing?

• What updates or steps would be needed to sell in the next 6–12 months?

Sometimes the most loving thing is giving yourself (or your parents) more ease and less upkeep.

2. “Should we keep the family home or pass it on?”

This is a conversation so many families tiptoe around; but it’s important.

Maybe it’s the childhood home.
Maybe it’s the vacation home in Annapolis that everyone loves.

This is a great time to ask:

• Is it realistic for the family to keep it long-term?

• Would selling it open doors for new dreams or investments?

• Should one family member buy out the others?

A clear conversation now prevents confusion or stress later.

3. “Is anyone thinking about buying in 2025?”

Whether it’s:
• a first-time buyer
• someone relocating
• a growing family
• or someone ready for their dream home

Thanksgiving is the perfect moment to talk about:

• Budget

• Location

• Must-have features

• Timing for pre-approval

• How to prepare now for a spring or summer move

Even a simple conversation helps everyone get aligned and gives you the chance to support each other in the process.

4. “Should we invest in a second home or rental property?”

Real estate is still one of the most powerful wealth-building tools for families.
Thanksgiving is a natural moment to explore ideas like:

• Buying a vacation home near the water

• Investing in a rental for long-term income

• Pooling resources for a shared investment

• Turning an underused property into something that works for the family

You never know where the conversation will lead — many of my clients have started their investment journey around the holiday table.

5. “What’s our real estate plan for next year?”

Goals don’t have to be complicated.

You can simply ask:

• What’s one real estate move we want to make in 2025?

• Is there a home we want to sell, improve, refinance or rent out?

• Is now the time to let go of a property that no longer serves us?

Clarity creates confidence and these conversations can bring your family closer while setting up a solid year ahead.

🌟 Final Thought

Thanksgiving isn’t just about food, it’s about home.
And the conversations you have around that table can shape your next chapter.

If you or someone in your family is thinking about buying, selling, downsizing, or investing in the Annapolis area, I’m here as your trusted advisor. I’ll give you real data, honest guidance, and a personalized plan that fits your goals.

Let’s talk whenever you’re ready.

I'm here every step of the way.

Cheers,

Katie Moore

📲 443-623-7887
💌 [email protected]