8 Waterfront Retreats on the Delaware & Maryland Market

Welcome to your dream waterfront retreat in Crownsville, MD! This charming cottage-style home offers cozy, comfortable living space, featuring 3 bedrooms and 2 bathrooms. The property sits on a picturesque, 1-acre lot, showcasing a private sandy beach with kayak storage and a playground, 2 piers, 2 boat lifts, a jet ski lift, a large parking pad, and multiple outdoor sheds. Experience the beauty of Severn River with expansive views from every angle while being conveniently close to Annapolis – either by boat or by car! Situated on a peninsula, this property has an approved conditional septic permit for a 3500 square foot, 5-bedroom home, offering endless possibilities for expansion.

Listing details: Embrace the tranquility of waterfront living and create unforgettable memories in this idyllic setting. Don’t miss the opportunity to own this slice of paradise in an exclusive waterfront location. Whether you’re seeking a weekend getaway or year-round residence, this is the perfect canvas for your waterfront lifestyle aspirations. Live your life on vacation! Note: This property includes 2 parcels totaling 45,872 square feet – over one acre total!

Luxurious Bayfront Retreat with In-Ground Pool and Private Dock Welcome to your dream oasis! This custom-built masterpiece, com- pleted in 2019, offers the pinnacle of coastal living. Nestled on 130 feet of pristine canal frontage to the Rehoboth Bay, this home boasts breathtaking water views and unparalleled tranquility.

Listing details: The spacious and custom, 4-bedroom, 3-bathroom residence spans 4,100 square feet and has been meticulously upgraded throughout. The open-concept design seamlessly connects indoor and outdoor spaces, with a grand living area featuring a glass wall that opens to the expansive patio. Outside, the in-ground pool invites you to unwind and soak up the sun, while the private dock allows you to launch your boat, kayak, or paddleboard directly from your backyard. Situated in an ex- clusive neighborhood, this home offers privacy while being just minutes away from dining, shopping, and entertainment. Whether you’re a water enthusiast or simply seeking serenity, this property delivers. Don’t miss this rare opportunity to own a slice of paradise. Schedule your private tour today!

A must see & truly one of a kind oceanfront townhome in the highly desirable neighborhood of North Shores in Rehoboth Beach. This end unit has been fully renovated from the studs out. The open floor plan on the main level flows from the beautiful oceanfront views to wonderful sunsets. Depending on how you want the layout to work for you it can be 5 to 6 bedrooms with 4 full bathrooms, stunning gourmet kitchen , wonderful one of a kind bathrooms and a oceanfront deck to enjoy and relax on with family and friends.

Listing details: Enjoy the beach and all the community has to offer with private beach, tennis courts and a swimming pool. Just a pedal away is the world class Gordon’s Pond bike trail through the Delaware State Park. Call today for your private tour.

Welcome to 37 Holly Road, a rare waterfront property on North Shore’s Yacht Basin, available for the first time since 1969. Located in a quiet cul-de-sac in private North Shores, it features close proximity to a private beach, community pool, tennis, and pickleball courts. The large yard includes a private dock with minimal boat traffic, perfect for sunbathing, crabbing, fishing, and launching water sports like kayaking and paddleboarding.

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Listing details: The main house has an open kitchen, living, and dining area with full-height glass walls and a large screened atrium. It includes an en suite bedroom, three additional bedrooms, 2 half baths, and a separate shower/tub room. The atrium offers natural daylight and a wonderful indoor-outdoor space for relaxing and gatherings. A separate cottage with central air, a bathroom, fireplace, and enclosed porch complements the property. With ample off-street parking, a sun deck, and an outdoor shower, this home, offered fully furnished, is the ideal vacation spot.

Are you looking for a rare find in Saint Mary’s County? The long paved 500 ft driveway to your secluded get away brings you a peaceful, tranquil feeling instantly. The all brick main house was built in 2012. The stunning property has 3,100 sq ft. on the upper level with every room facing the water, wrap around deck, spectacular views from every angle and breathtaking sunrises and sunsets daily. The upper level has 16 ft. vaulted ceilings in the living area and 10 ft. ceilings in the remaining rooms. Family room with stone gas fireplace, formal living room and dining room, all with hardwood floors. There is a huge master bedroom with gas fireplace, walk in closet and adjoining master bath with jacuzzi tub and spa, walk in double shower.

Listing details: A very large dream kitchen with all high-end appliances, 2 refrigerators, 2 Bosch dishwashers, a double Wolf wall ovens and large Wolf gas range. Sub Zero ice maker in the wine bar, 5×6 center island all granite tops, and all the cabinets one can want and a walk-in pantry. There are 2 bedrooms with a jack and jill bathroom in between, guest powder bath in hallway, office with adjoining bath and laundry room. As you descend to the lower level that is completely finished with another 3,100 sq ft with 11 ft ceilings, a huge master bedroom with large bath and walk in spa shower and very large walk-in closet. The family room has a massive stone, wood burning fireplace and separate pool room, awesome theater room, tiki bar for entertaining, and another bedroom and large bathroom. All rooms have walk out doors to the beach area, patio, and pier with 2 boat slips with 5-6 ft. depth as well as property boat ramp at the end of the road. There is an Amish 14×24 barn with loft across from garage. The four-car garage has a full bath and guest house above which has 1600 sq. ft. that includes 2 large bedrooms, 2 baths a laundry room with an open kitchen to family room and living area. This too boasts beautiful water view’s from a large deck where one can enjoy the scenic wild life. This 2.39 mostly wooded waterfront with a bulkhead and its own private sandy beach is a once in a lifetime find, located close to Pax Naval Station, a few minutes away from Leonardtown and California MD with plenty of shopping and entertainment close by. Do not miss out on a once in a lifetime opportunity and breath taking property to have your own piece of paradise.

Very rarely does a property like this one come on the market. Builders’ contemporary waterfront home finished in 2013, on 22+/- acres on Madison Bay in Woolford, MD, with additional guest home. Offering extreme privacy, the main home has 3 or 4 BR, 3 BA, office, multilevel with hardwood floors throughout, 3 car garage, basement with utilities and geothermal heating/air conditioning.

Listing details: The guest house has 3 BR, 2 BA, and 2 car garage with 10 ft door for boat storage, half BA, utility room, and office. Both homes have raised decks with magnificent sunset views over the bay and their private 300 ft sandy beach. The land has two natural ponds, large level lawn areas great for sports, undisturbed mature pinewoods with numerous deer, and waterfowl for hunting or just enjoying the privacy and 1000 ft of waterfront. The property is sited on a cul-de-sac county road.

Discover a waterfront haven on the Wye River with over 2 acres of luxury living just across from Wye Island. This meticulously renovated residence offers over 8,000 sqft of grandeur and comfort, featuring multiple living areas, a gourmet kitchen, formal dining room, library, and a luxurious primary suite. Recent high-end renovations seamlessly blend modern sophistication with timeless charm, including upgraded appliances, custom wallpaper, chandeliers, and hardwood floors.

Listing details: Breathtaking river views greet you from every room, while outdoor spaces boast landscaped gardens, a private dock, waterfront patio, and an Olympic-sized swimming pool with panoramic water views. Nestled on a private corner of Wye Road in Queenstown, this property offers both privacy and security with easy access to amenities, making it the epitome of waterfront luxury living on Maryland’s Eastern Shore. Schedule a tour today to experience the captivating grandeur of 200 Wye Road.

Nestled along the sparkling shores of Chesapeake Boy, this exquisite custom-built home built in 2023-24, stands as a testament to luxury and refined living. No detail has been overlooked in the creation of this magnificent residence, where no expense was spared to craft a haven of beauty and comfort.

Price: Contact for pricing

Listing details: The enchanting sunsets each evening offer a spectacle. Take in the panoramic views of the bay, feel the gentle breeze, and immerse yourself in the serenity of waterfront living. Experience a lifestyle of luxury and tranquility in this Chesapeake Bayfront retreat, where every day is a celebration of nature’s splendor and the essence of waterfront living.