Your Eastern Shore Real Estate Expert
Make this place your home.
Specializing in Waterfront, Town, and Lifestyle Properties
Courtney Chipouras, REALTOR® | TTR Sotheby’s International Realty
Settle into the Soul of the Shore
I’m Courtney Chipouras, a top-rated real estate agent with TTR Sotheby’s International Realty, serving Maryland’s Eastern Shore — including Kent, Queen Anne’s, and Talbot Counties.
Whether you’re dreaming of a waterfront retreat, a walkable in-town home, or land to build your own Eastern Shore sanctuary, I’ll help you find a property that matches your lifestyle and values.
With over 9 years of experience and a passion for the shore’s landscapes and communities, I’ll guide you through every step of your buying or selling journey.
As Seen In
Specializing in Eastern Shore Waterfront & Water-Oriented Homes
From the Sassafras to the Choptank, and all the quiet covers, tidal creeks, and rivers in-between, I help clients buy and sell the Eastern Shore’s most treasured waterfront properties. Whether you’re looking along the Chester, Wye, Miles, Tred Avon, or Eastern Bay, I bring hyper-local insight, Sotheby’s-level marketing, and a trusted network that makes every move seamless.
What My Clients are Saying
Serving Kent, Talbot & Queen Anne’s Counties
With offices in Chestertown and Easton, I proudly serve clients across:
Kent County
Chestertown, Rock Hall, Galena, Betterton
Queen Anne’s County
Centreville, Grasonville, Queenstown, Kent Island
Talbot County
Easton, St. Michaels, Trappe, Oxford, Royal Oak
Local knowledge matters in this market and I know every cove, creek, and community worth exploring.
Explore the Eastern Shore’s Communities
Discover the charm of Maryland’s Eastern Shore, one community at a time. From the historic streets of Chestertown to the sailing culture of St. Michaels and the peaceful beaches of Betterton, each town offers something unique. Use my local guides to explore real estate, schools, lifestyle, and hidden gems across Kent, Talbot, and Queen Anne’s Counties.
White-Glove Service Tailored To Your Goals
As a Sotheby’s International Realty agent, I bring world-class marketing, global reach, and luxury service no matter your price point. But what truly sets my work apart is the care and personal attention I bring to every client relationship.
Whether you’re selling a beloved family home or searching for your next chapter on the Shore, I’ll walk with you every step of the way with compassion, responsiveness, and unmatched attention to detail.
Luxury Marketing For All Property Types
Trusted Local Network & National Brand Power
Thoughtful, Hands-On Guidance Start to Finish
“If you are looking for a Real Estate Agent, look no further — you found her!
Courtney was an absolute pleasure to work with. This was a very emotional time for me, and she genuinely cared about what I was going through… She always made me feel like I was her only client.”
— Client, Estate Sale of Family Waterfront Home
Explore the Shore: Lifestyle, Towns & Property Tips
Check out the blog for insider insights, local guides, and real estate advice.
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There's something special about walking into a space that just feels right—and often, that magic comes from the details you don’t even notice at first glance. That’s exactly what Erin Zierfuss of Common Thread Interiors brings to the homes she designs here on the...
A Couples’ Guide to Winter in Kent County, Maryland
Looking for a cozy winter escape with your favorite person? Discover Kent County’s most romantic spots: from fireside dinners to peaceful waterfront strolls. Whether it’s a weekend getaway or a peek into future retirement, this guide is your invitation to slow down and savor the season together.
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.
Let’s Find Your Eastern Shore Home
Whether you’re relocating, upsizing, downsizing, or simply ready for a change, I’m here to help you navigate the Eastern Shore real estate market with confidence.
