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Caroline County

Known as the Green Garden County, Caroline’s rural landscape and relaxing lifestyle have lured farmers and families to plant roots here for two centuries. Set on the mid-Shore between the Choptank River and the Mason-Dixon Line, Caroline is bordered by three counties to the west – Queen Anne’s, Talbot and Dorchester – and Sussex County Delaware to the east.

Attractions include Tuckahoe State Park, Adkins Arboretum and the Fiber Arts Center. Residents enjoy easy access to the Queenstown outlets. Caroline offers many rural locations with lot sizes ranging from 1 acre to 5 acre+ sites with generally high ground and pockets of smaller neighborhood communities.


As the county seat of Caroline, Denton became a trade center for a wide agricultural area when it was created in 1774 from parts of Dorchester and Queen Anne’s counties. The recently opened “Wharves of Choptank Heritage & Visitor Center” on the Choptank River is attracting new commerce: Tourists and paddle enthusiasts eager to explore Denton’s history, recreation and culture. Denton is also home to a growing artisan and culinary community.

Today, professionals working on the western shore from Annapolis and Baltimore to DC are planting roots in Denton and Caroline County thanks to accessible commutes, affordable homes, and serene, high quality of life.


A peaceful, close-knit community, Preston is a mix of original descendants, new families attracted to a growing business community, and retirees wanting convenient access to the Delmarva peninsula.

Old mansions and early-period homes, moved from old farmsteads during Preston’s early days, stand side-by-side in harmony with newer modern communities on Apple Lane and Tidewater Farms. Companies expanding or relocating here include Choptank Transport, Preston Automotive Group, Crystal Steel and Benedictine.

Area Listings