Make this place your home.
Courtney Chipouras, REALTOR® on Maryland’s Eastern Shore
Big rivers, small towns, connected communities, an unspoiled Chesapeake landscape.
I’m Courtney Chipouras. As a real estate agent, I’m passionate about helping my clients find their perfect Eastern Shore home. I specialize in water-oriented and waterfront properties on Maryland’s Eastern Shore. Whether you’ve dreamed of your own waterfront sanctuary, a town home within walking distance of the farmer’s market, or acreage to build the private retreat you’ve always imagined, I can’t wait to help you start ‘living pleasantly’ in Kent, Queen Anne’s, and Talbot Counties.
Real Estate Agent on the Eastern Shore of Maryland
Looking for something specific? My listings change frequently, so check back often to explore the latest residential, commercial, and property listings.
What My Clients are Saying
“If you are in the market for real estate on the Eastern Shore, I highly recommend that you contact Courtney Chipouras. She is a well-connected and respected realtor in the Kent & Queen Anne’s county areas. Courtney went above and beyond during the entire process and made sure that we found a property that fit our needs. Local knowledge plays a key factor in finding the best properties for the best price.”
– Client, Rock Hall, Maryland
Welcome Home to Maryland’s Eastern Shore
I’m Courtney Chipouras
And I can’t wait to help you make this place your home. 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.
Explore the Eastern Shore’s Communities & Landscapes
Small towns, big stories.
Holiday Guide to Maryland’s Eastern Shore (2025 Edition)
Looking for holiday fun on Maryland’s Eastern Shore? From twinkling parades and boat shows to Dickens-themed festivals, this guide has everything you need to celebrate the season in classic Eastern Shore style.
How to Choose the Best 55+ Active Adult Community on Maryland’s Eastern Shore
Considering a 55+ community on Maryland’s Eastern Shore? Discover how to choose the perfect fit in our newest guide. We break down key factors—from the right county and community size to amenities, HOA rules, and location—so you can find a neighborhood that fits your lifestyle and retirement goals. Whether you’re imagining waterfront views on the Bay, a quieter setting in a smaller enclave, or easy access to charming towns and cultural amenities, we’ve got the insights to help you make an informed choice.
Is Rock Hall Right for You? A Realtor’s Take on Small Town Coastal Charm
Rock Hall, Maryland, known as the “Pearl of the Chesapeake,” is a small waterfront town with big appeal. From lively marinas and breathtaking sunsets to its warm sense of community, Rock Hall blends coastal beauty with small-town charm. But is it the right fit for your lifestyle — or your next home? Here’s a Realtor’s take on what makes Rock Hall so unique.