Ocean Pines Homes for Sale

Ocean Pines Homes for Sale

Welcome to Ocean Pines, Maryland—a charming coastal community nestled in the heart of Worcester County. Just a stone's throw away from the vibrant beaches of Ocean City, this picturesque town offers the perfect blend of tranquility and adventure. With its stunning waterfront views, lush green spaces, and a welcoming atmosphere, Ocean Pines is an ideal place to call home.

Ocean Pines is renowned for its beautiful homes, ranging from cozy beach cottages to spacious family residences, making it a perfect fit for first-time buyers, retirees, and everyone in between. The real estate market here is thriving, with a variety of homes for sale that cater to diverse tastes and budgets. Whether you’re looking for a serene retreat or a vibrant community lifestyle, you’ll find it all in Ocean Pines.

In addition to its stunning properties, Ocean Pines boasts an array of amenities that enhance the quality of life for its residents. Enjoy leisurely afternoons at one of the community’s parks, take a dip in the pool, or explore the scenic walking trails. The area also features a variety of shops, restaurants, and recreational activities, ensuring there’s always something to do.

With its friendly community spirit and a wealth of natural beauty, Ocean Pines is more than just a place to live; it’s a lifestyle waiting to be embraced. If you’re ready to find your dream home in this idyllic setting, explore the homes for sale in Ocean Pines today and start your journey towards a vibrant coastal life!

Newest Ocean Pines Homes for Sale

$875,000
3 Beds 3 Baths
We're going to call this canal-front because technically, that's what it is. Just don't expect it to look like most canal-front homes in Ocean Pines!! Walk out back and you'll understand the difference. Instead of staring across a narrow canal at another row of homes, the water (and views) open up considerably.... with no homes blocking your view, you're given a stunning view of the Ocean Pines Golf Course, and beyond. Plus, you get the boating access you're looking for in a waterfront home. Let's move on to the house itself.... At approximately 2,500 square feet, this 3-bedroom, 3-full-bath home gives you something else that's surprisingly difficult to find on the waterfront in Ocean Pines: SPACE. There's a true two-car garage, generous living areas, a three-season room overlooking the water, and a large first-floor deck that turns the backyard into a pretty compelling reason to spend more time outside. Plus, the interior has been extensively renovated with a new kitchen, new bathrooms, new flooring, new central HVAC, and fresh paint throughout. The result, when you walk in the front door into a vaulted 2-story living room, is impressive! This is an established waterfront home that's already had the major interior updating that you don't want to have to do yourself. Out back is where everything starts coming together. The property includes a bulkhead and private dock with water suitable for boats, paddle-boarding, and kayaks....giving you the ability to keep the boat (and water toys) in your back yard. The three-season room provides another place to enjoy the waterfront when the weather doesn't cooperate... because this is Maryland and apparently we're required to experience all four seasons in the same week (you know I'm right)!. There's no 'one thing' that separates this home from other waterfront homes in the area.... It's "all the things" that make it stand out. The lot size, the quiet street, the attached garage, the renovations, the vaulted ceilings, the waterfront location, the views, and the price point! That's what makes this home at 84 Newport so interesting. Ocean Pines has grown into one of the area's most complete residential communities, with miles of waterfront, parks and recreation, pools, racquet sports, boat ramps and kayak launches, the Ocean Pines Golf Club, Yacht Club, and even its own Beach Club in Ocean City. You're positioned within an easy drive of Berlin, Ocean City, Assateague Island, shopping, restaurants, healthcare, and everything else that makes northern Worcester County such a desirable place to live. At $875,000, we're offering a waterfront home that 'offers' more than most. And we'd love to help make this your home.

84 Newport Dr, Ocean Pines

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400

$399,000
2 Beds 2 Baths
Welcome home to this lovingly cared-for, one-owner home, designed by an interior decorator. This retreat nestled among the towering trees in the desirable North Gate of Ocean Pines one of the safest places to live in Maryland and just minutes from the beautiful beaches, dining, and entertainment of Ocean City, Maryland, Assateague and Rehoboth beaches. Medical facilities, schools, yacht club, and golf course nearby. Situated on a serene, private lot backs to Briarcrest Park, this charming 2-bedroom, 2-bath home also features a spacious loft that can easily be converted into a third bedroom, home office, or flex space to suit your needs. Filled with warmth and character, the great room showcases soaring cathedral ceilings accented by stunning exposed wood beams, unique moon-shaped architectural openings, and a cozy wood-burning stove that creates the perfect gathering place. The wood stove provides ambiance and warmth on cold winter nights as well as peace of mind with possible energy loss! Laminate hardwood flooring flows throughout the main living areas, while the tiled kitchen is equipped with a stainless-steel refrigerator and offers both functionality and style. The first-floor bedroom features sliding glass doors leading to a vinyl-tech enclosed screened porch, providing a peaceful spot to relax and enjoy the surrounding nature. Double sliders from the great room open to an expansive wraparound deck, seamlessly blending indoor and outdoor living and offering the perfect setting for entertaining or simply enjoying the tranquil wooded backdrop. Outside, you'll find an outdoor shower, storage shed, and convenient U-shaped driveway. Major updates include a roof and HVAC system that are approximately five old. Home is complete with pull down attic stairs and encapsulated crawl space. This wooded retreat can be yours now to enjoy year-round. Call for your private showing!

6 Briarcrest Dr, Ocean Pines

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

$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

$1,749,900
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

$388,000
3 Beds 2 Baths
Welcome to coastal living at its finest in sought-after Ocean Pines, Maryland! Discover this beautifully updated 3-bedroom, 2-bath home that has been completely renovated from top to bottom. Every detail has been thoughtfully refreshed, offering a true move-in-ready experience just minutes from the beaches of Ocean City. Interior Highlights Totally renovated kitchen — modern finishes, perfect for everyday living or entertaining Fully renovated bathrooms with contemporary updates New vinyl plank flooring throughout the main living areas for durability and style New carpet in the bedrooms for added comfort Inviting gas fireplace ideal for cozy evenings year-round Outdoor Living Step outside to your brand-new wrap-around deck — the perfect spot for morning coffee, evening relaxation, or entertaining friends and family while enjoying the wooded, coastal surroundings of Ocean Pines. Ocean Pines Lifestyle & Amenities As a resident of Ocean Pines, you’ll enjoy access to one of the premier residential communities on Maryland’s Eastern Shore (amenities available via optional a-la-carte memberships): Five swimming pools (including indoor and outdoor options, plus the Ocean Pines Beach Club in Ocean City) Robert Trent Jones Sr.–designed championship 18-hole golf course Premier racquet sports complex with tennis, pickleball, and platform tennis Two marinas and the scenic Yacht Club with bayfront dining Private Beach Club oceanfront facility in Ocean City (with resident parking privileges) Multiple parks, walking & biking trails, community center, farmers market, and year-round recreation programs Own police and fire departments for added peace of mind Located just a short 10–15 minute drive to Ocean City’s beaches, boardwalk, dining, and entertainment, yet nestled in a quieter, wooded community with over 3,000 acres and more than nine miles of waterfront property. Ocean Pines offers the ideal balance of resort-style amenities and relaxed Eastern Shore living.This renovated home is ready for its next owners to enjoy the best of coastal Maryland living. Don’t miss this opportunity!

6 Weeping Willow Ct, Ocean Pines

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

$539,900
3 Beds 2 Baths
This stunning ranch-style home, set on a beautifully landscaped lot, offers a harmonious blend of luxury and comfort. The interior boasts over 1,500 sq. ft. of thoughtfully designed space, featuring three bedrooms and two full bathrooms. The front bedrooms are perfect for guests or as a private office. The heart of the home is the expansive kitchen, complete with an island, stainless steel appliances, and a cozy breakfast bar, seamlessly flowing into the dining area with recessed lighting, and the house is adorned with crown molding throughout. Major renovations in 2024 have elevated this residence, including new roof, interior paint, doors, fixtures, lighting, and appliances. Enjoy the warmth of the electric fireplace in the living area, enhanced by abundant natural light from skylights and insulated windows. The primary suite features a double door entry, tray ceiling, walk-in closet and a spa-like bathroom with a walk-in shower, lighted faucets, and shiplap walls/ceiling. From the light-filled sunroom, step outside to discover a covered porch, fire pit, extensive hardscaping, pea gravel, a hot tub, and multiple patios perfect for entertaining or relaxing amidst the serene backdrop of trees, vinyl fencing, and gardens. The community offers an array of amenities, including pools, tennis courts, and walking paths, fostering an active lifestyle. Located in a vibrant neighborhood within walking distance to popular restaurants, bars and conveniences. With easy access to recreational facilities and a welcoming community atmosphere, this property is a true gem for those seeking a blend of luxury and lifestyle.

1036 Ocean Parkway, Ocean Pines

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

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