Meet Your Property Matchmaker

I'm Courtney Chipouras, and I can’t wait to help you make the Eastern Shore your home.

As a native of Maryland’s Eastern Shore, I bring my deep knowledge of the communities, landscapes, and waterfront of the Chesapeake region to my clients, helping them find their commercial or residential property in Kent, Queen Anne’s and Talbot Counties. 

With a strong business background and a deep love for Maryland’s Eastern Shore, I bring a unique perspective to real estate—one that blends sharp business acumen with a true understanding of what makes this place so special. 

My journey started with an MBA from Wilmington University and nearly two decades of global corporate experience with Verizon, where I excelled in sales leadership, relationship-building, business development, and account management. Along the way, I was honored to earn a spot in Verizon’s President’s Club multiple times and was named the Top Client Executive—Overall for Verizon Enterprise Solutions in 2016. Although I left the corporate world in 2017 when I got my real estate license, those years of experience taught me the power of strategic negotiation, market insight, and top-tier customer service—skills that now translate directly into helping my real estate clients make informed, confident decisions.

But beyond business, what truly sets me apart is my deep connection to this region. The Eastern Shore isn’t just where I work—it’s home. Born and raised in Kent County, I know its rhythms, its hidden gems, and the way life moves a little slower here, just the way we like it. Whether you’re looking for a waterfront retreat, a historic home with character, or the perfect spot to put down roots, I take pride in helping my clients find a property that not only meets their needs but also fits their way of life.

Bringing people and places together is more than a career—it’s a calling. And there’s no greater privilege than helping folks find their perfect piece of the Shore.. It has been one of the biggest privileges of my life and I can’t imagine doing anything else.

When I’m not helping my clients find their perfect property, I live with my husband on Little Greenwood Creek in Queen Anne’s County, and I’m thankful to have returned to my Eastern Shore roots. I also believe deeply in our Chesapeake community, and value giving back through volunteerism and board commitments. Currently, I serve on the board of the Queen Anne’s County Mental Health Committee.

Contact me today at courtney@mychesapeakehome.com