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$545,000
5 Beds ⋅ 2 Baths
Waterfront investment opportunity in Ocean Pines! 2 Windjammer Rd represents an incredible chance to buy into a premier coastal location at a low waterfront price point and build instant equity through your own improvements. Please note: This is an trustee sale. The property is being sold strictly AS-IS and is priced accordingly. Bring your vision and tools to this classic handyman special! The spacious main house features 2,258 square feet of potential, boasting a side porch with vinyl tech windows, and a rear deck perfect for entertaining. The unique layout offers incredible versatility with an open floor plan for the living/dining/kitchen areas. There are a total of 5 bedrooms and 2 full baths in the main house- 2 beds and 1 bath on entry level, 3 beds and 1 bath on upper level. The second-floor balcony provides private access (with additional steps from the ground level) to a separate room over the garage. This bonus area includes finished, climate-controlled guest quarters (approx 600 sq feet) complete with its own full bathroom, kitchenette, and stairs to loft area. The over-sized 2 car garage is attached to the main home by a deck/breezeway and offers space for covered parking plus workshop area and additional storage. Boaters and water lovers take note: the true highlight of this property is its prime waterfront location. Enjoy your own private dock with direct access out of the canal and into Assawoman Bay. There is a long list of amenities in Ocean Pines, including: championship golf course, five swimming pools (including an indoor pool and the oceanfront Beach Club in Ocean City), two marinas, racquet sports, a yacht club, and multiple parks and trails. Positioned in an ideal coastal hub, you are just a short drive from the historic charm of downtown Berlin, the legendary beaches and boardwalk of Ocean City, MD, and the pristine, natural beauty of Assateague National and State Beaches. Don't miss this rare waterfront flip, rental asset, or dream coastal project!

2 Windjammer Rd, Ocean Pines

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$359,900
3 Beds ⋅ 2 Baths
Adorable and affordable! Built by American Homes, this charming, well-maintained 3-bedroom, 2-bath rancher is ideally located near the Swim & Racquet Club pool and White Horse Park. The bright, open floor plan features cathedral ceilings, a combined Living, kitchen and dining area, and a separate laundry room off the kitchen. Relax on the inviting front porch or enjoy the spacious rear deck. Recent updates include fresh paint, roof replacement with warranty (2019) , newer HVAC, newer washer and dryer, and refrigerator, new microwave stove and dishwasher. Newly LVP flooring in the living room, dining room, and kitchen, new bathroom flooring and raised toilets, plus an encapsulated crawlspace. A flooring allowance is available for the bedrooms which are currently bare. Enjoy this low-maintenance home near the beach year-round or as a getaway. Don’t miss it—this one won’t last long! Carpet allowance for bedrooms

304 Ocean Parkway, Ocean Pines

Listing courtesy of PW Realty Sales, LLC. Contact: 4432298888
$499,900
3 Beds ⋅ 2 Baths
Welcome to your coastal retreat in the heart of Ocean Pines! This beautifully remodeled 3-bedroom, 2-bath A-Frame contemporary offers breathtaking golf course views with a peaceful canal backdrop, combining modern updates, exceptional outdoor living, and an unbeatable location. Whether you're searching for a primary residence, second home, or vacation getaway, this move-in ready property offers the best of Maryland's Eastern Shore lifestyle. Inside, you'll find an open floor plan filled with natural light, soaring cathedral ceilings, luxury vinyl plank flooring, and a beautifully updated gourmet kitchen featuring upgraded countertops, stainless steel appliances, and modern finishes. Thoughtfully renovated bathrooms and quality updates throughout create a home that is both stylish and functional. Step outside to enjoy extensive hardscaping, multiple outdoor entertaining areas, and a private fenced backyard overlooking the golf course—perfect for relaxing after a day at the beach, on the golf course, or out on the water. Select furnishings are negotiable, offering buyers the opportunity to purchase a truly turnkey property. Ocean Pines residents enjoy an exceptional amenity package, including indoor and outdoor pools, a championship golf course, marina, yacht club, boat ramps, parks, walking trails, playgrounds, dining, clubhouse, and year-round community events. Located just minutes from Ocean City, you'll have easy access to beautiful beaches, the famous Boardwalk, restaurants, shopping, fishing, boating, and endless entertainment. Offering an exceptional combination of location, updates, views, and lifestyle, 72 Newport Drive is a rare opportunity to own a beautifully renovated golf course home in one of the Eastern Shore's most sought-after coastal communities. Schedule your private tour today!

72 Newport Dr, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 3025391777
$995,000
4 Beds ⋅ 3 Baths
Exceptional canal-front home with a pier and direct access to the bay. Thoughtfully updated throughout, this spacious 4-bedroom, 2.5-bath home offers the potential for a 5th bedroom and features new windows, flooring, renovated bathrooms, and an updated kitchen. Modern glass stair railings add a stylish contemporary touch, while the primary suite boasts a generous walk-in closet. Enjoy stunning water views from the spacious living areas, screened porch, and multiple decks. Outside, the beautifully landscaped and fenced yard provides the perfect setting for entertaining or relaxing by the water. Additional features include a fireplace, attached 2-car garage, and pier for boating, fishing, and crabbing right from your backyard. Ideally located just around the corner from one of Ocean Pines waterfront beach clubs, residents can enjoy convenient access to a pool, sandy beach area, and waterfront recreation. Enjoy all the amenities Ocean Pines has to offer, including pools, golf, marina, yacht club, parks, and beach club access. Whether you're looking for a year-round residence, vacation getaway, or investment opportunity, this exceptional waterfront property offers the best of coastal living.

9 Harborview Dr, Ocean Pines

Listing courtesy of Coastal Life Realty Group LLC. Contact: (443) 235-8382
$340,000
3 Beds ⋅ 2 Baths
Opportunity awaits with this 3-bedroom, 2-bath home featuring a cozy fireplace, screened-in porch, fenced backyard, and a new hot tub. The functional floor plan and desirable outdoor living spaces provide a great foundation for customization. Located in the popular community of Ocean Pines, this property provides access to an impressive selection of amenities, including swimming pools, a golf course, a marina, a beach club, parks, and scenic walking paths. Enjoy the best of coastal living with Ocean City’s beaches, restaurants, shops, and entertainment just a short drive away. Whether you're looking for a primary residence, vacation getaway, or investment opportunity, this home offers an excellent location with endless possibilities.

11 Bimini Ln, Ocean Pines

Listing courtesy of Coastal Life Realty Group LLC. Contact: (443) 235-8382
$979,900
5 Beds ⋅ 3 Baths
This beautifully renovated 5-bedroom, 3 full bath canal-front beach retreat is ready for its next chapter. Thoughtfully updated by a trusted local home improvement company, the home is nearly complete. Recent upgrades include a new roof, siding, windows, and doors, along with fully renovated bathrooms, a new kitchen, water heater, and a new lower-level HVAC unit. A brand-new extra-high garage door and an oversized one-car garage provide ample space for storage, including taller vehicles and all your beach and water gear. The main level features an open-concept living space designed for gathering, complemented by three bedrooms, including a private en-suite. The lower level adds exceptional flexibility with a spacious family room, two additional bedrooms, a full bath, and a large laundry/utility room. Experience the best of coastal living with expansive upper and lower decks overlooking the canal and your private dock ready for you to pull up your boat. perfect for relaxing or entertaining. Enjoy your own private boat dock with effortless access to open water—no bridges to slow you down, just smooth sailing right from your backyard. Close to local beaches and all that Ocean City has to offer, you’re just minutes from golf, dining, swimming, and the area’s popular farmer’s market.

8 Grand Port Rd, Ocean Pines

Listing courtesy of ERA Martin Associates, Shamrock Division. Contact: 4106415000
$429,000
3 Beds ⋅ 2 Baths
Turnkey Retreat in Ocean Pines’ Sought-After North Side, Offered Furnished Tucked away on a quiet cul-de-sac in one of Ocean Pines’ most desirable north-side neighborhoods, this charming 3-bedroom, 2-bath coastal home is move-in ready and offered fully furnished. The main living area features cathedral ceilings and an open loft, creating an airy, spacious feel perfect for relaxing or entertaining. The loft is ideal as a home office, rec room, or easily converted into a 4th bedroom. The kitchen shines with granite countertops and newer stainless appliances, all set on low-maintenance laminate flooring throughout. Unwind by the cozy pellet stove on cool evenings, relax on the screened back porch, or enjoy the fully fenced backyard. Private, peaceful, and perfect for pets, kids, or entertaining. A large storage shed, outside shower, and generous driveway round out the exterior, with ample lot space for a boat, garage, or future addition. Upgrades include: new roof (2017), encapsulated crawl space (2020), new kitchen appliances (2020), and a new split-system ductless HVAC with electric baseboard backup (2020). Walk to the Swim & Racquet Club, Little Beach, the Farmers Market, and the Community Center. Launch a kayak to the St. Martin River or Assawoman Bay in minutes. Ocean City’s beaches are just a short drive away. As an Ocean Pines homeowner, you’ll enjoy resort-style amenities: golf, yacht club dining, indoor and outdoor pools, boat ramps, tennis, walking and biking trails, dog park, baseball, basketball, and exclusive Ocean City beach parking and beachfront pool access.​​​​​​​​​​​​​​​​

53 Grand Port Road, Berlin

Listing courtesy of O'Conor, Mooney & Fitzgerald. Contact: (410) 449-4900
$569,000
3 Beds ⋅ 2 Baths
Waterfront, Great Price, Featuring 60 feet of bulkhead with deep water access and private dockage directly behind the home, this property is perfect for boating enthusiasts. Inside, you’ll find an open floor plan designed for comfortable coastal living, along with a spacious screened porch and large rear deck—ideal for entertaining or relaxing after a day on the water. The home also includes a two-car garage and a newer roof installed approximately two years ago. Conveniently located just off Ocean Parkway, the property offers easy access in and out of the community and is close to local amenities including the Ocean Pines Golf Club, community pools, and boat ramp. Enjoy quick boat access to the St. Martin River, making this an excellent option for a primary residence, second home, or investment opportunity. A great chance to secure an affordable waterfront property just in time for summer.

354 Ocean Parkway, Berlin

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty-WOC. Contact: 4105202600