Notes from My Chesapeake Home

Sharing local stories, market trends, and real estate advice for buyers and sellers across Maryland’s Eastern Shore.

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.

Buying Land in the Chesapeake

Buying Land in the Chesapeake

With real estate inventory limited across the Eastern Shore region, many buyers are turning to land as an investment or to build a custom home that meets their specific needs. It can be a smart move. Selecting a place for its peaceful vistas, small towns and sunsets across open water first—and...

Long Distance Chesapeake House Hunting

Long Distance Chesapeake House Hunting

The small communities, water views, and rural peace and quiet of the Eastern Shore are legendary—and in today’s market, more people than ever before are looking for their own slice of Chesapeake paradise. That competition has incentivized many buyers from more urban areas far away, and many of...

Six Essential Questions for Buying a Home

Six Essential Questions for Buying a Home

Buying a home in the Chesapeake is not just a transaction—like a turtle tucking back beneath the waterline, you’re immersed in the unique charm and beauty of the region. And whether you're drawn to the historic waterfront towns or the tranquil rural landscapes, it's crucial keep your priorities in...

The Best Home Upgrades with the Highest Returns

The Best Home Upgrades with the Highest Returns

Investing in the comfort and value of your home through improvement projects is a time-honored strategy—especially when those upgrades will help sellers to take full advantage of the Chesapeake’s booming real estate market. Whether aiming to elevate your home's appeal or stay competitive in the...

The Benefits of Rightsizing

The Benefits of Rightsizing

Fall in the Chesapeake is a time of migration. For all the songbirds and osprey that have summered here and raised their young, it’s time to fatten up for their long flights south to overwinter and to leave their Bay nests behind. Huge murmurations of them pour through the beeches and oaks,...

Summertime Eastern Shore Dock Bars

Summertime Eastern Shore Dock Bars

The Eastern Shore is a water world in all seasons of the year, but especially summer. Quiet coves are suddenly full of the bright buoys of crab pots and trotlines. Mooring balls are spoken for, tethering sailing and power boats, and families splash at the water’s edge wherever the shoreline turns...

Landscape Tips to Help Your Home Sell

Landscape Tips to Help Your Home Sell

As the Eastern Shore’s spring somes to an end, it’s time to get out the gardening gloves. For many homeowners, it’s a seasonal tradition and an enjoyable way to make your yard as lovely and inviting as possible. It’s also a major selling point for prospective homebuyers, and is often the first...

Celebrating the Eastern Shore, Throughout the Seasons

Celebrating the Eastern Shore, Throughout the Seasons

Throughout the year, the communities of the Eastern Shore create different ways to celebrate the season. Distinctive to each county’s landscape and traditions, these festivals and events annually enliven life in Talbot, Queen Anne’s and Kent County. For locals, visitors and newcomers, they...

New Year, New Resolutions

New Year, New Resolutions

The beginning of a New Year always comes with the promise of a fresh start, and nothing speaks to the possibilities like resolutions. There’s self betterment, whether scrolling on your phone less or reading that book that’s been sitting on your bedside table for months. Physical improvements, like...

Wings & Whitetail Farm: an Eastern Shore Country Estate

Wings & Whitetail Farm: an Eastern Shore Country Estate

Sep 19 From a gentle rise overlooking a quiet tributary of Langford Creek, the main house of Wings & Whitetail Farm surveys the landscape as it has for 265 years. Once called “Bungay Hill,” this 18th century home in Kent County, Maryland is one of the county’s most important historic...

Featured Property, 5781 Main St, Rock Hall

Featured Property, 5781 Main St, Rock Hall

A “third space.” Every community has them. Barbershops, churches, coffee shops, VFW’s, local parks. Gathering places that aren’t home, aren’t work, but welcome you in to come together and socialize. In Rock Hall, the Old Oars Inn Bar and Restaurant on Main Street was a beloved third space. A...