Bishopville, MD Homes for Sale with Acreage

Waterfront Estate | Headwaters of the Shingle Landing River | Positioned on over two private waterfront acres at the headwaters of the Shingle Landing River, this exceptional custom residence by White Creek Homes, Inc. embodies refined coastal living at its finest. Encompassing over 7,000 square feet, the home offers 7 bedrooms, 5 full baths, and 3 half bath, thoughtfully designed to balance

Erik Windrow Keller Williams Realty

Discover unmatched coastal living in this 5‑bedroom, 4.5‑bath waterfront retreat, perfectly positioned on a picturesque point along Grey’s Creek off Assawoman Bay. Offering 330 feet of private waterfront, this property delivers sweeping water views, unforgettable sunsets, and a rare blend of privacy, space, and tranquility—just minutes from the ocean yet worlds away from the bustle.A

Nicholas Elko O'Conor, Mooney & Fitzgerald

Escape to your own private retreat on 5.41 acres while enjoying the convenience of being just minutes from restaurants, shopping and the beach. Tucked away from the road, this custom-built 5-bedroom, 3.5-bath home features an open floor plan with 10-foot ceilings, hardwood flooring throughout the main living areas, and a living room with a gas fireplace. The chef's kitchen is equipped with a

Bethany Drew Hileman Real Estate-Berlin

Now, on to this beautiful home. This is a Custom brick-front contemporary on 1.43 wooded acres in Piney Island, one of Bishopville's most sought-after neighborhoods: a quiet, established community of custom homes on large wooded lots, most of them on the water, tucked well off Route 113 with bay views at the end of the street. Minutes from the Delaware line and about 15 minutes to Ocean City.

Jonathan Minerick Homecoin.com

Nearly 19 private acres, minutes from the water, in a part of Bishopville where land like this almost never comes up. Mature trees screen the property from the road and the neighbors, and that privacy sets the tone before you even reach the front door. A large porch with wood-beamed ceilings and a stone patio gives you a place to sit outside well after dark. Step through the front door into a

Jules Burchett Foraker Realty Co.

ONCE UPON A TIME in a sweeping coastal vista with an architectural world-class design, there is a TIMELESS, premiere Lighthouse Sound estate. Truly an unparalleled level of both privacy and prestige. Fashioned in the classic Shingle-Style design, otherwise known as "Coastal Seaside Architecture"...MANY EXPENSIVE HOMES ARE LARGE, BUT FEW EXPENSIVE HOMES ARE PROPORTIONED THIS WELL. The symmetry

Beth Evans Berkshire Hathaway HomeServices PenFed Realty

Welcome to 10220 Shingle Landing Road, an impressive estate offering over 5,600 square feet of living space on more than 4.5 beautifully landscaped acres. Located in an exclusive setting of just five estate-sized homesites, this exceptional property offers privacy, space, and versatility—all just a few miles from the beaches of Ocean City. This expansive home features 6 bedrooms and 5.5

Jim Terrill RE/MAX One

Never before offered. One of the most pristine, incredible waterfront properties that has been fully approved, subdivided, utilities in place, roads in place, boat docks in place, all lots perc approved and ready for the new owners. 16 total lots, 1 of which is 165+- acres of open space with ample marsh lands. 15 subdivided lots ranging in size from 2+ acres to 11.57 acres. 10 of the 15

Ken Church Coldwell Banker Bud Church Realty,Inc.

MOTIVATED SELLER JUST REDUCED another $100K and OFFERING 5% OWNER FINANCING - CALL LISTING AGENT FOR DETAILS! Bring your buyers and offers for this beautiful new construction home nestled within the prestigious Lighthouse Sound community!! This exceptional 2025 new construction residence offers the perfect blend of coastal elegance, natural beauty, and modern luxury. Set on an expansive 1.22-acre

Donna Harrington Coldwell Banker Realty

Welcome to 12355 Southampton Drive, the crown jewel of Lighthouse Sound, one of the Eastern Shore's most prestigious waterfront golf communities. This is a rare opportunity to own arguably the finest homesite in the neighborhood, where this extraordinary custom residence captures sweeping panoramic views of Assawoman Bay and the sparkling Ocean City skyline from nearly every rear-facing room. A

Ann Buxbaum Northrop Realty

NEW PRICE for your dream home that is waiting for you here on 2 acres! Custom built in 2006 to replace an older primary home; this quality home has 3 bedrooms- the primary is on the first floor along with a luxurious primary bath and walk-in-closet. Guest 1/2 bath. 2 additional bedrooms and bath are on the second floor. Formal Living room and dining room greeting you along the foyer entrance.

Marlene Ott Berkshire Hathaway HomeServices PenFed Realty - OP