Ocean Pines Homes with Contemporary Style

Ocean Pines Homes with Contemporary Style

Welcome to Ocean Pines, Maryland – a hidden gem nestled in the heart of Worcester County. This vibrant community, just a stone's throw from the stunning Atlantic coastline, offers a unique blend of serene living and recreational opportunities that make it an ideal destination for families, retirees, and everyone in between.

Ocean Pines is renowned for its picturesque landscapes, featuring lush greenery, tranquil waterways, and an abundance of wildlife. With its close proximity to Ocean City, residents enjoy easy access to beautiful beaches, exciting boardwalk attractions, and a variety of dining and shopping options. The community is also home to a plethora of amenities, including golf courses, parks, and community centers, ensuring that there’s always something to do.

When it comes to real estate, Ocean Pines boasts an impressive selection of contemporary-style homes that perfectly complement the area's natural beauty. These modern residences feature open floor plans, large windows that flood the interiors with light, and sleek architectural designs that appeal to today’s discerning buyers. Many homes also offer outdoor living spaces, allowing you to soak in the stunning views and enjoy the mild Maryland climate.

Living in Ocean Pines means embracing a lifestyle that balances relaxation with adventure. Whether you’re taking a leisurely stroll along the scenic walking trails, enjoying a day of fishing on the bay, or participating in community events, there’s always a sense of belonging in this charming locale. Discover the allure of Ocean Pines and explore the contemporary homes that await you in this idyllic coastal community. Your dream home is just a visit away!

Newest Ocean Pines Homes with Contemporary Style

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

4 Beds ⋅ 5 Baths

Situated on a private, serene half-acre waterfront lot in the desirable Colonial Village section of Ocean Pines, this spectacular 4-bedroom, 3 full bath, 2 half bath home offers over 4,289 square feet of beautifully designed living space with exceptional indoor and outdoor amenities. The home is strategically positioned via view-oriented architecture to guarantee water views. Just a short stroll to the Ocean Pines Yacht Club, two community pools, the Pines Point Provisions restaurant, and the Pines Point Marina; this is coastal living at its finest. From the moment you step inside, you'll appreciate the thoughtfully designed floor plan that perfectly balances comfort and functionality. The spacious living room, casual dining room, and inviting family room to provide the perfect setting for entertaining family and friends or simply relaxing. The chef's kitchen is sure to impress with upgraded quartz countertops, premium Viking appliances, and abundant workspace. The luxurious first-floor primary suite is a peaceful waterfront retreat featuring breathtaking water views, a beautifully updated spa-inspired bath, and an oversized walk-in closet with plenty of space for two. The inviting family room, complete with a cozy fireplace, opens to a covered waterfront deck—the perfect place to enjoy your morning coffee or unwind with an evening drink while taking in the tranquil surroundings. A charming four-season gazebo creates the ideal setting for crab feasts, outdoor dining, and relaxing while enjoying the refreshing coastal breezes. The first floor also features a convenient laundry room and two half baths. Upstairs, you'll find three spacious guest bedrooms, two full baths, a dedicated exercise room, and a second covered waterfront deck where you can enjoy spectacular water views and seasonal fireworks. Step outside to your own private waterfront oasis. The expansive backyard offers plenty of room for children and pets to play, while boating enthusiasts will appreciate 105 feet of waterfront with a bulkhead replaced in 2025, a 16,000-pound boat lift, and dockage that can accommodate boats up to approximately 70 feet with easy access to the open bay. The protected canal is perfect for kayaking and paddleboarding, and dolphins are often spotted swimming by, making every day feel like a vacation. Additional improvements include two HVAC systems replaced in 2025 and 2026, a tankless water heater approximately seven years old, an encapsulated crawl space, a spacious 2.5-car garage, and ample driveway parking. This smart home is equipped with security cameras and an alarm system for added peace of mind. Best of all, this exceptional waterfront home is being sold fully furnished, making it truly move-in ready. Simply bring your suitcase and start creating unforgettable memories with family and friends in one of Ocean Pines' most sought-after waterfront communities. Flood Zone X no flood insurance required. Water depth in low tide is 5Ft 6".

538 Yacht Club Dr, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

2 Beds ⋅ 2 Baths

Welcome to easy, one‑level living in The Parke at Ocean Pines—the perfect retirement community for active adults who want comfort, convenience, and a vibrant social lifestyle. This move‑in‑ready home offers everything you need on a single floor, with spacious rooms, natural light, and low‑maintenance living. Step outside to your newly added rear patio, backing to peaceful trees—an ideal spot for morning coffee, afternoon reading, or relaxing outdoors in total privacy. The Parke is known for its friendly, active atmosphere, offering endless opportunities to stay engaged: farmers markets, food trucks, social clubs, fitness classes, and special community events throughout the year. Enjoy resort‑style amenities including an indoor pool, clubhouse, walking trails, and access to all Ocean Pines facilities. Located just minutes from Ocean City’s beaches, golf courses, marinas, and restaurants, this home gives you the best of coastal living with the peace and privacy of a 55+ neighborhood. Perfect as a full‑time residence or a low‑maintenance second home near the shore. Move right in and start enjoying the lifestyle you’ve been waiting for.

13 Hatteras St, Ocean Pines

Listing courtesy of Samson Properties. Contact: 7033788810

3 Beds ⋅ 3 Baths

Located in the highly desirable Teal Bay neighborhood, this charming 3-bedroom, 3-bath home has been meticulously loved and maintained. The flexible floor plan features primary suites on both the first and second floors, along with an updated kitchen and bathrooms, a screened in porch, garage, private backyard, and encapsulated crawlspaces. Enjoy a peaceful view of the St. Martin River from the sunroom without the added cost and upkeep that comes with waterfront living. Natural light floods the home, creating a bright and welcoming atmosphere while the spacious upstairs primary suite features two walk-in closets and a private second-floor balcony. Find your serenity in this prime coastal location, just minutes from the beach with all the exceptional amenities Ocean Pines has to offer!

180 Teal Cir, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

3 Beds ⋅ 3 Baths

Seller and family are working to remove their personal items collected over their many years of ownership and enjoyment. Some minor handyman work being taken care of also and it should be available to see and fall in love in a few weeks. This is a Duane Maddy, Piney Island Builders, classic contemporary with all your "I wants". Formal Living room greets you as you enter and that leads to the large Family Room, kitchen and dining area. 12x12 screened porch and 20x12 deck for outdoor enjoyment. New roof in 2022 and Encapsulated Crawl space in 2017. In 2014, new kitchen granite countertops and all new appliances. An additional room was added that could be a Bunk Room or Office.

62 Martinique Cir, Ocean Pines

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

3 Beds ⋅ 3 Baths

A lovely home, a great location, and a great price! Tucked in the serene confines of Sherwood Forest, and yet only a short distance to South Gate of Ocean Pines, this charming 3 Bedroom, 2.5 bath home features 2 FIRST FLOOR bedrooms. One first floor bedroom features an en suite half bath, the full bath is in the hall for both bedrooms to share. Upstairs there is a bedroom, full bath, and a large bonus room with plenty of possibility. Just some of the many features in this home are an open floor plan, updated kitchen with stainless steel appliances, updated bathrooms, gas fireplace, and beautiful LVP floors through the living room, sunroom, and kitchen. Outside there is a deck on the front of the home, a balcony in the rear. Plus a paved driveway and a storage shed. This home is just what you are looking for, schedule a showing today!

7 Royal Oaks Dr, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

4 Beds ⋅ 3 Baths

Featuring over $80,000 in brand-new capital upgrades—including a brand-new bulkhead, new dock, new roof, and newer dual zone HVAC system with full ductwork—this premier Wood Duck Isle estate offers immediate boating access with absolute structural peace of mind. Perfectly positioned near the end of a canal with beautiful views stretching across Manklin Creek, this spacious 4-bedroom, 2.5-bath waterfront home offers the ideal blend of comfort, quality, and coastal living. Meticulously maintained and thoughtfully updated, the current owners have invested extensively in the home's major systems and waterfront features. Designed for both everyday living and entertainment, the first floor features a spectacular waterfront primary suite with a beautifully updated bathroom and an oversized walk-in closet. A dramatic two-sided brick gas fireplace creates a warm focal point, shared between the primary bedroom and the dining room. The main level also includes a spacious waterfront great room with hardwood flooring, a sunroom filled with natural light, a private den or study, a powder room, and a well-appointed kitchen conveniently located just beyond the mudroom/laundry room, which connects directly to the oversized two-car garage. Upstairs are three distinctive bedrooms and an updated full bathroom, providing plenty of space for family and guests, along with easily accessible attic storage. Step outside to embrace the waterfront lifestyle with an 8,000-pound boat lift, professionally enhanced with numerous mechanical upgrades. Whether you're heading out for a day on the water or simply relaxing while taking in the peaceful creek views across Manklin Creek, this property is a true boater's retreat. If you've been searching for a meticulously maintained waterfront home with lovely views, generous living spaces, exceptional updates, and easy boating access, this is an opportunity you won't want to miss!

74 Wood Duck Dr, Ocean Pines

Listing courtesy of ERA Martin Associates, Shamrock Division. Contact: 4106415000

5 Beds ⋅ 6 Baths

Welcome to one of Ocean Pines’ most extraordinary waterfront estates, where luxury, recreation, and coastal living come together in a truly one-of-a-kind offering. Situated on a beautifully positioned waterfront homesite with 75 feet of newly bulkheaded shoreline, this remarkable residence encompasses approximately 9,200 square feet of thoughtfully designed living space with 5 bedrooms, 5.5+ baths, and an unmatched collection of resort-style amenities. Designed for entertaining on every level, the home features a spectacular 63-foot indoor pool with a 7-foot depth, private locker room, movie theater, expansive game room with wet bar, sunroom, and an oversized chef’s kitchen that opens seamlessly into light-filled living and dining spaces framed by soaring ceilings and walls of glass overlooking the water. The outdoor living experience is equally impressive. Enjoy expansive waterfront decking, an enclosed brick courtyard with a charcoal grill, multiple spaces for gathering, a rooftop observation deck with panoramic views, and direct boating access from your private dock featuring an 8,000-pound boat lift. Whether hosting family and friends or enjoying a quiet evening overlooking the water, every space has been designed to embrace the coastal lifestyle. Additional highlights include a two-car garage, generous driveway and guest parking, and the home is offered fully furnished (with select exclusions), allowing you to begin enjoying it from day one. Properties of this caliber are exceptionally rare. Whether you’re searching for an extraordinary primary residence, an unforgettable coastal retreat or the ultimate waterfront investment property, 23 Mallard Drive East delivers a lifestyle few properties can match. Schedule your private showing today and discover what life on the water was meant to be!

23 Mallard Dr E, Ocean Pines

Listing courtesy of Atlantic Shores Sotheby's International Realty. Contact: (410) 524-0919

3 Beds ⋅ 2 Baths

Welcome to this well-maintained home in the desirable Nantucket section of Ocean Pines, offering the perfect blend of comfort, functionality, and low-maintenance living. Situated on a nicely wooded lot with just the right amount of privacy, the yard is easy to maintain while still offering plenty of opportunity for gardening or additional landscaping. Enjoy relaxing on the inviting front porch or unwind in the fenced backyard featuring a fire pit and seating area, perfect for entertaining or quiet evenings at home. Inside, this gently used second home has been meticulously cared for. The flexible floor plan includes a main-level bedroom and full bathroom, making it ideal for guests or first-floor living. The combined living and dining area is anchored by a cozy wood-burning fireplace, while engineered hardwood flooring runs throughout the home with beautifully stained oak stairs adding warmth and character. The kitchen offers abundant Thomasville cabinetry, generous storage, and a practical layout designed for everyday living. Just off the Kitchen area, you will find the spacious four-season room provides endless possibilities as a home office, TV room, reading nook, hobby space, or additional gathering area. Additional features include: • HVAC replaced in 2020 • Nest smart thermostat • Main-level laundry • One-car garage with built-in storage and dehumidifier • Crawlspace dehumidifier • Updated shower fixtures • Freshly painted upstairs bathroom with a modern LED vanity mirror featuring adjustable brightness and color temperature Whether you're looking for a full-time residence, weekend getaway, or beach retreat, this home offers comfort, thoughtful updates, and the Ocean Pines lifestyle just minutes from Ocean City beaches, dining, golf, marinas, and shopping. Sellers are offering a ***$5,000*** credit towards the roof.

10 Gloucester Rd, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

4 Beds ⋅ 3 Baths

Quality Craftsmanship meets exceptional care in this beautifully maintained home, built by Piney Island Builders. Neatly nestled on a large private lot backing to peaceful woods in the heart of Ocean Pines, this home offers the perfect blend of comfort, privacy, and timeless appeal. Designed for easy living, the home features a spacious first-floor primary suite, providing convenience and flexibility for everyday life. Recent updates include a newer roof, composite decking, and updated kitchen appliances, allowing you to move in with confidence. Step outside and enjoy the beautifully landscaped Backyard, where you'll find a charming treehouse and plenty of space to relax, entertain, or simply take in the serene wooded setting. A large garage offers ample room for vehicles, storage, and hobbies. Two more outbuildings, a large shed, and an adorable greenhouse complete the yard. This exceptional home showcases quality construction, thoughtful updates, and a peaceful setting -making it a wonderful opportunity to enjoy all that Ocean Pines has to offer

20 Frigate Run, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

3 Beds ⋅ 3 Baths

Enjoy this charming, contemporary three-bedroom-plus home, beautifully nestled among mature trees on an oversized lot at the end of a peaceful cul-de-sac. With inviting living spaces, step through the front door into a spacious open living area with soaring ceilings, bathed in natural sunlight. The space features hardwood flooring and a cozy wood-burning fireplace, creating a warm and welcoming atmosphere. And there is an adjacent office or den. Flexible Bonus Room and Updated Features: A special feature of the home is the converted garage, which now serves as a versatile room—perfect for a home business, office, exercise room, or hobbies. This space includes a separate entrance and a half bath for added convenience. Adjacent to the laundry room, you will find a large walk-in pantry with abundant shelving, an additional refrigerator, and a chest freezer. The primary bedroom and bath are conveniently located on the first level, while the second level offers two additional bedrooms, a full bath, and a generous walk-in attic, providing ample space and flexibility for your needs. Recent updates include a brand-new roof with architectural shingles, and the warranty will transfer to the new owners. The HVAC system was updated in 2022. The interior was freshly painted throughout, all carpeting has been replaced with a neutral shade, and the wood flooring has been sanded to look like new. Outdoor Living and Curb Appeal: Relax or enjoy steamed crabs on summer evenings in your three-season porch with a tiled floor, overlooking the private backyard. The front yard is nicely landscaped and features an antique Japanese lantern, adding a touch of elegance. A large driveway provides ample parking for guests. This is a must-see home! Experience life in Ocean Pines, an award-winning community filled with amenities such as indoor and outdoor swimming pools, a championship golf course designed by Robert Trent Jones, tennis and pickle ball courts, a Yacht Club and Marina, Beach Club, Community Center, Saturday Farmers Market, library, Post Office, shops, restaurants, and more—delivering prime coastal living.

10 Laurel Trl, Ocean Pines

Listing courtesy of Hileman Real Estate-Berlin. Contact: (410) 208-9200

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

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