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.
Waterfront Living in Rock Hall: What You Need to Know
Rock Hall, known as the “Pearl of the Chesapeake,” offers more than just a weekend escape — it’s a way of life. From sweeping Bayfront views and charming marinas to quiet coves perfect for boating and crabbing, waterfront living in Rock Hall, MD combines small-town warmth with timeless coastal beauty. Whether you’re considering a full-time residence or a seasonal retreat, here’s what to know before making Rock Hall your Eastern Shore home.
A Local’s Guide to Chestertown This Fall (Beyond the Festivals)
Everyone knows about Chestertown’s iconic fall festivals — like Downrigging Weekend — but what do locals actually do once the sails are down and the crowds have gone home?
If you’re thinking about moving to Kent County or simply want to experience Chestertown like a local this season, this guide is for you. From quiet riverfront walks and cozy cafés to hidden gallery pop-ups and scenic backroad drives, here are all the ways to enjoy autumn on the Eastern Shore — beyond the big events.
Living in Kent County: A Realtor’s Perspective
Considering a Move to Maryland’s Eastern Shore? Discover what it’s really like to live in Kent County—from a local Realtor who lives and works here. Whether you’re relocating, retiring, or just craving a quieter pace of life, this post gives an honest, insider’s perspective on the charm, community, and character that make Kent County feel like home.