Eastern Shore Towns and Locales

Historic Chestertown is set on the banks of the Chester River on the Eastern Shore of Maryland. From quaint cottages to stunning waterfront homes, condos and farms, you’ll find boundless choices of Chestertown properties for sale. Stroll along the River and brick walkways lined with 18th century homes, shops, cafes, theater and Washington College. Located in Kent County about 90-minutes from Washington, D.C. and Philadelphia. Chestertown is a great location for year round living or second homes.

Diverse commercial and business offerings on the Eastern Shore provide numerous prospects and opportunities for business owners and entrepreneurs. They range from small retail shops, historic homes/offices and B&B's in the historic districts of Chestertown, Easton and other quaint towns. Marinas, horse farms, restaurants, convenience stores, gas stations and office buildings are available for sale throughout the counties.

The Eastern Shore is known for its wildlife habitat and scenic landscape of fields and waterways. Kent County is mainly agriculture with a rich history of farming, crabbing and oystering. In Talbot County, approx. 65,000 acres of land are subject to Chesapeake Bay Critical Area protection. Of this, about 5,600 acres are tidal wetlands. With miles of scenic Chesapeake Bay waterways and fertile farmland, Queen Anne’s County real estate include waterfront farms, residential and adult communities.

This region features the most shoreline and points of public waterway access sites of any region in the Maryland, thanks to the hundreds of coves, bays, rivers and islands that are found here. Diverse waterfront offerings range from spectacular waterfront homes with sweeping views and deep water docks, to cottages nestled in the woods on creeks perfect for kayaks, waterfront farms for hunting, condos, beachfront and residences with breathtaking sunset views of the Chesapeake Bay.

Kent County Real Estate offerings include residential, country houses, waterfront farms, cottages and historic homes in picturesque towns. The second oldest county in Maryland, Kent County was founded in 1642 and is situated in the northern part of the Eastern Shore. Primarily rural, the Kent County's population has changed little over the last 100 years, and there remains a strong sense of community. Residents enjoy access to the Chesapeake Bay, Chester River and other waterways.

Kent County is bounded by Delaware on the east, the Sassafras River on the North, the Chesapeake Bay on the West and the Chester River on the South. Real Estate offerings include waterfront estates, beach cottages, water-access communities, condos and hunting farms. Quiet coves offer fishing, canoeing or kayaking. Anchorages, marinas and public landings are available throughout the County. Betterton Beach, located near the mouth of the Sassafras River, is ideal for swimming and famil…

Known as “Maryland’s Gateway to the Eastern Shore,” Kent Island sits at the base of the Chesapeake Bay Bridge and is a rapidly growing community because of it’s convenience to the Annapolis/Baltimore-Washington corridor. Kent Island is the largest island in the Chesapeake Bay. It is 4.2 miles wide and 15 miles long. Real estate properties range from in-town residential neighborhoods to extraordinary waterfront estates on the Chesapeake Bay, Cox Creek, and Eastern Bay.

Oxford is one of Maryland's oldest towns charted back to a 1673 map of Maryland and Virginia. It served as an important port for vessels from all over the world. Oxford, Maryland is a protected harbor for watermen who harvest oysters, crabs, clams and fish. The waterfront town is recognized for its small town charm with cottages and historic homes along the Tred Avon River. Boaters, weekend visitors and summer residents enjoy the quiet ambiance of this special seaside town.

Queen Anne's County forms the "gateway to the Eastern Shore” with 265-miles of waterfront area, much of that being the shores of Kent Island. With miles of scenic Chesapeake Bay waterways and fertile farmland, real estate offerings include waterfront homes, farms residential and adult communities. Tree-lined streets showcase Colonial period homes and gracious Victorian dwellings. Queen Anne's County is named for Queen Anne of Great Britain who reigned when the county was established in 1706.

Rock Hall was an important tobacco port, then later a major fishing and crabbing center. Life-long residents share the waterways, the fishing village and shops with seasonal boaters and tourists. Rock Hall is a unique destination for visitors from all over the world who enjoy boating. With its location right on the Chesapeake Bay, there are opportunities to rent a small boat or kayak for a day. In addition, larger boats are available for bare-boat chartering and captained bay cruises.

The quaint seaside town of St. Michaels is located about halfway between the Susquehanna source and the Atlantic mouth of the Chesapeake Bay. St Michaels dates back to the mid-1600s when it served as a trading post for area tobacco farmers and trappers. Real Estate in St. Michaels ranges from historic homes, waterfront cottages, and condos. Enjoy seeing the town by water with a cruise on THE PATRIOT.

Located directly on the Chesapeake Bay, Talbot County has always been famous for its crabbing, oyster harvesting and extensive wildlife. It has over 600 miles of tidal shoreline - the most of any county in the United States. Waterways in Talbot County include the Chesapeake Bay, Choptank River, Tred Avon River and Wye River. Talbot County Real Estate offers diverse options including waterfront estates, cottages, and historic homes in rural settings and picturesque waterfront towns.