Welcome to the Land of Pleasant Living

Maryland's Eastern Shore

Queen Anne's County

Queen Anne’s County is the gateway to the Eastern Shore, entering just as you cross the Chesapeake Bay Bridge.  Many scenic waterways provide the perfect backdrop for a variety of real estate options.  There are Colonial period homes, farms and estates, and newer waterfront communities offering a plethora of amenities and condos and cottages to provide trouble-free weekend getaways.  The boating community is very active, with several top-notch marinas in the area.  Kent Island is also a popular bedroom community because of the easy access to Annapolis, Baltimore, and Washington DC.  Centreville, the county seat, is a charming town with more traditional small-town trappings—tree-lined streets, historic and new single-family communities, and farms.  You’ll find shopping, dining, and plenty of nature trails sprinkled throughout the remaining towns of Chester, Stevensville, and Queenstown.  In addition to the Bay Bridge, popular attractions include Tuckahoe State Park, Terrapin Nature Park, Chesapeake Bay Environmental Center, Matapeake Park, and the Cross Island Trail.

Learn More 

Kent County

Kent County is the smallest County in Maryland but has the most shoreline.  Kent County is a predominantly agricultural area steeped in rich maritime history, celebrating events such as the Chestertown Tea Party and the Sultana Downrigging Weekend.  To live in Kent County is to appreciate a slower pace, and residents enjoy the small-town lifestyle of Chestertown, home to Washington College, and proximity to Rock Hall, known as the "Rockfish Capital of the World" or Betterton Beach for a day of relaxing by the water.  You’ll also find vineyards, shopping, waterfront dining, art galleries, live theater, and music within this charming county. 

Learn More

Caroline County

Caroline County is a quintessential rural community.  The majority of commerce and landscape is farming.  Denton, the county seat, was once an important shipping point for agricultural products. Today, residents enjoy a town that sits high on the banks of the Choptank River, with access to a variety of recreational opportunities.  Preston was the sight of three Underground Railroad stations, most notably one operated by Harriet Tubman.  Federalsburg, located on Marshyhope Creek, has recently enjoyed growth and expansion, with more development. Ridgely, another small town, is most known as “The Strawberry Capital of the World."  You'll also find grand Victorian homes that give the nod to the prosperous canning days. Popular area attractions include Adkins Arboretum, Martinak State Park, Tuckahoe State Park, and the Museum of Rural Life.

Learn More

Talbot County

Talbot County, often referred to as "The Hamptons of the Chesapeake," comprises Easton, Oxford, St. Michaels, and Tilghman Island, as well as some smaller villages.  There are over 600 feet of shoreline along the tributaries of the Chesapeake Bay, providing ample opportunities for waterfront living.

Easton, the County Seat, enjoys all the conveniences of a jet airport, shopping centers, and hospital, with a mix of waterfront and inland neighborhood communities.  St. Michaels, perhaps most famous for being the location where the movie “The Wedding Crasher’s was filmed, is bursting with nautical ambiance along small historic streets.  Oxford is a tiny town most known as a haven for sailors, and Tilghman Island is an authentic waterman's village. 

Popular attractions include the Chesapeake Bay Maritime Museum, the Avalon Theatre for music and shows, the downtown areas of Easton and St. Michaels; check out the winery, brewery, and distilleries in St. Michaels, Pickering Creek, and the Oxford Bellevue Ferry.

Learn More

Dorchester County

Dorchester County, dubbed the “Heart of the Chesapeake” because of its heart-shaped borders, is an Eastern Shore destination that has much to offer the outdoor lovers, foodies, history buffs, art lovers, and athletes. 

The largest town is Cambridge, the county seat, and other communities include Church Creek, East New Market, Hurlock, Secretary, Vienna, Fishing Creek, Madison, and Taylors Island.

Blackwater National Refuge is home to thousands of migratory birds and a popular place to enjoy the countryside and striking marsh views.  Historically significant as home to Harriet Tubman, you can explore the path where she led others to freedom along the Harriet Tubman Underground Railroad Byway. 

While much of the county comprises marshland, forest, and farms, you'll also find grand historic homes in Cambridge along the water and many neighborhoods sprinkled among the farmland.  The Hyatt Regency Chesapeake Bay also offers condo and townhome-style properties.

Learn More