Notes from My Chesapeake Home
Sharing local stories, market trends, and real estate advice for buyers and sellers across Maryland’s Eastern Shore.
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.
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.
Why I Love Kent County in the Fall (And Why You Might, Too)
There’s something about fall in Kent County that just feels... right. The crisp air. The steady roll of golden cornfields. The way the trees wrap the two-lane roads in a tunnel of color. And maybe most of all—the peaceful sense of time slowing down, just a little. As someone who lives and works...
Navigating a Shifting Market on Maryland’s Eastern Shore
After years of rapid growth, Maryland’s Eastern Shore real estate market is finding new balance. Whether you’re selling a home or thinking about buying, Fall 2025 brings fresh opportunities—if you know how to navigate the changes. In this post, I break down what today’s market means for pricing, timing, and smart strategy on both sides of the transaction.
What to Know About Condo Living on Maryland’s Eastern Shore
Condominiums have long been a popular choice in the U.S. housing market, and that’s just as true today in 2025. While traditional single-family homes remain the gold standard for many, condos offer an appealing alternative, especially for buyers who value convenience, community, and...
Become More Active in Your Chesapeake Community This Spring
Spring on Maryland’s Eastern Shore brings returning osprey, waterways waking up from winter, and a fresh wave of opportunities to emerge from hibernation and get involved in your community. Whether you're a lifelong resident or newly settling in, now is the perfect time to connect, give back, and...
Spring Selling on Maryland’s Eastern Shore: Tips for a Fresh Start
pring on the Eastern Shore brings new life—and new listings. Local real estate agent Courtney Chipouras shares expert tips to prepare your home for sale this season and avoid common seller pitfalls.
What Every Chesapeake Homeowner Needs to Know About Insurance
If you own a home on Maryland’s Eastern Shore, your insurance needs may be different than you think. Learn what’s covered, what’s not, and how to protect your coastal property the right way.
Winter Guide to Maryland’s Eastern Shore: Events, Cozy Finds & Local Charm
Last Modified: October 2025 Discover the Magic of the Shore in Winter Winter on Maryland’s Eastern Shore offers a peaceful kind of charm that’s hard to find anywhere else. Without the summer crowds, you can explore historic towns, dine fireside, sip wine in cozy tasting rooms, and attend some...