Plebe Summer & Finding the Right Fit in Real Estate

Oct 4, 2019 | Eastern Shore Life

There’s something about the word home that our men and women in the military understand better than the rest of us ever could. The people who sacrifice the most for our safety often miss out on the simple comforts we all enjoy every day. That’s why my husband and I wanted to find a way to give back.

Living just over the bridge from Annapolis, we learned about the US Naval Academy’s sponsorship program, which gives new students — known as “Plebes” — a home away from home as they adjust to their rigorous training. Every summer, around 1,600 Plebes arrive for Induction Day and seven intense weeks of Plebe Summer, beginning their journey from civilians to Midshipmen. It’s an honor and a huge responsibility.

Becoming Sponsor Parents

After moving back to Maryland, Steve and I applied to be sponsor parents. The application process was surprisingly thorough — almost like filling out a dating profile. They wanted to make sure plebes were matched with families who truly fit their needs and personalities. We emphasized our love of sports, the outdoors, and hosting, and asked to be paired with someone from farther away so we could provide more consistent support.

That’s how we met Cole, our Midshipman from Franklin, Tennessee. A state champion wrestler and quarterback, Cole was athletic, hardworking, and all-around a great young man. We had the privilege of supporting him through a big transition — and ultimately watching him find his perfect fit on the rugby team after football wasn’t the right match.

Lessons That Apply to Real Estate

Being sponsor parents reminded me so much of what I do every day in real estate. Just like Cole had to find his fit at the Academy, buyers and sellers need to find their fit in a home and a community.

A house isn’t just about square footage or finishes — it’s about how it fits your lifestyle, your family, and your future plans. Sometimes buyers think they know exactly what they want, only to realize that what they really need looks a little different. My job is to listen, guide, and stick with them until we find the right fit.

Questions Every Buyer Faces

When searching for a home, most buyers wrestle with questions like:

  • Should we live closer to highways or choose a more private location?
  • Do school districts outweigh square footage?
  • Is a one-level home better for us long-term, or would two stories work better now?

Like plebes adjusting to Academy life, buyers often discover that they can’t have everything at once — and that’s okay. The key is deciding where to compromise and where to hold firm.

Finding the Right Fit in Real Estate

Whether you’re new to the Eastern Shore or looking to put down roots in a familiar community, the process is about more than just buying a house — it’s about finding the right fit in real estate. That’s where a trusted guide makes all the difference.

Just as Steve and I supported Cole through his journey at the Academy, I’m here to walk alongside my clients, helping them weigh their options, make informed decisions, and ultimately find a place that truly feels like home.

Ready to Find Your Fit?

Every buyer’s journey is unique. Some know exactly what they want; others discover it along the way. Either way, I’d love to help you find your perfect fit here on Maryland’s Eastern Shore.

Contact me today to start your search!

Courtney Chipouras, TTR Sothebys Realtor on the Eastern Shore of Maryland

I’m Courtney, and I’m proud to live and work on Maryland’s Eastern Shore.

I’ve spent my whole life in this region, and I genuinely enjoy helping people find a place that feels like home. Whether you’re drawn to quiet waterfront living, small-town charm, or a home that gives you room to grow, I’m here to guide you through the process with honesty, care, and local insight.

If you’re exploring life on the Shore and want something who truly understands the area, I’d be happy to help you get started.

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Courtney Chipouras at her annual Pie Party event

Thinking About Making a Move to Maryland's Eastern Shore?

Whether you’re looking for a change of pace, a stronger sense of community, or just more time near the water, I’d love to help you figure out if the Eastern Shore lifestyle is right for you.

Let’s find the place that fits your next chapter.