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101 White Sail Cir, Ocean Pines
$465,000
3 Beds ⋅ 2 Baths
Buyers failed to sell their home. Tucked along the canal in the sought after community of Ocean Pines, this charming A-frame retreat blends rustic cottage character with the laid back waterfront lifestyle you’ve been dreaming of. With soaring vaulted ceilings, oversized windows, and an open layout designed to capture natural light and tranquil water views, this home is ready for relaxing weekends, family gatherings and entertaining after a day on the water. Step outside to enjoy the expansive wraparound deck overlooking the canal, the perfect place for morning coffee or evening sunsets. Boaters will appreciate the shared dock with a dedicated private slip for the home, offering easy access to the water. A cozy fireplace adds warmth and charm to the inviting living space, while the garage provides additional storage for all your beach and boating essentials. The main level features two bedrooms, a full bathroom, and a convenient laundry closet. Upstairs, the loft overlooks both the water and the main living area, creating a bright and airy retreat. The primary suite is also located on the upper level and showcases more dramatic vaulted ceilings that enhance the home’s unique architectural style. Located in Ocean Pines, residents can enjoy access to an incredible lineup of amenities including pools, parks, golf, marinas, trails, a beach club, and more, all just a short drive from the beaches, dining, and entertainment of Ocean City!

101 White Sail Cir, Ocean Pines

Listing courtesy of Atlantic Shores Sotheby's International Realty. Contact:

Selling Office: Keller Williams Realty Delmarva.

6 Harborview Dr, Ocean Pines
$615,000
3 Beds ⋅ 3 Baths
Enjoy waterfront living in this inviting 3-bedroom, 3-bath canal-front home located just a short distance from the open bay. Designed to make the most of its waterfront setting, the home features a spacious screened porch, upper-level deck, and patio with built-in seating, providing multiple places to relax, entertain, and enjoy the views. Inside, the kitchen offers tile flooring and pantry storage and opens to the dining area for easy everyday living. The upper level features a bedroom, full bath, and versatile loft space. Additional highlights include a newer roof installed in 2017, HVAC system replaced in 2018, water heater installed in 2024, and partial furnishings included. Whether you are searching for a primary residence or waterfront getaway, this home offers comfort, flexibility, and an ideal coastal lifestyle.

6 Harborview Dr, Ocean Pines

Listing courtesy of Hileman Real Estate-Berlin. Contact:

Selling Office: RE/MAX Advantage Realty.

50 Windjammer Rd, Ocean Pines
$449,900
3 Beds ⋅ 3 Baths
Welcome to this gorgeous, turnkey home in the amenity-rich community of Ocean Pines! Beautifully updated and thoughtfully maintained, this home offers a warm and inviting layout with stylish upgrades throughout. The spacious enclosed porch provides the perfect spot to relax and enjoy the surrounding scenery, while the brick steps and paved driveway add great curb appeal. Inside, you’ll find charming, exposed wood beams, a cozy fireplace, and beautiful finishes that make this home truly move-in ready. The two-car garage offers plenty of space for parking and storage. Out back, enjoy your own private retreat with a gazebo—perfect for entertaining or relaxing outdoors. Conveniently located near the Ocean Pines Golf Course and Yacht Club, with easy access to all of Ocean Pines’ fantastic amenities. A must-see home that combines comfort, character, and an ideal location!

50 Windjammer Rd, Ocean Pines

Listing courtesy of Coastal Life Realty Group LLC. Contact:

Selling Office: Atlantic Sands Realty.

354 Ocean Pkwy, Berlin
$550,000
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 Pkwy, Berlin

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

Selling Office: ERA Martin Associates, Shamrock Division.

22 Sailors Way, Ocean Pines - Berlin
$364,500
3 Beds ⋅ 2 Baths
13K PRICE IMPROVEMENT! Welcome to 22 Sailors Way, a well-maintained one-level 3-bedroom, 2-bath home tucked away on a quiet cul-de-sac in the heart of Ocean Pines. Designed for easy living, this ranch-style home features cathedral ceilings, a spacious primary suite, Andersen windows, a wood-burning fireplace, and an oversized one-car garage. Freshly painted throughout with brand-new carpet in the bedrooms, this home is move-in ready and waiting for its next owner. Enjoy outdoor living from the screened porch overlooking the large, private lot. This property is conveniently located near White Horse Park, the Community Center, and the Swim & Racquet Club. Whether you're looking for a primary residence, vacation getaway, retirement home, or investment opportunity, this home offers exceptional value in one of Ocean Pines' most desirable locations.

22 Sailors Way, Ocean Pines - Berlin

Listing courtesy of Bunting Realty. Contact:

Selling Office: Coldwell Banker Realty.

2 Windjammer Rd, Ocean Pines
$500,000
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:

Selling Office: Atlantic Shores Sotheby's International Realty.

31 Driftwood Ln, Berlin
$620,000
3 Beds ⋅ 2 Baths
Come Enjoy Coastal Living in the Sought-Out Community of Ocean Pines!  This 3 Bedroom 2 Full Bath WATERFRONT move-in Ready Home shows pride of ownership and is waiting for you!   Live the good life you have been waiting for!  Boat Dock, Boat Lift, Detached Garage, Three Season porch, all conveniently located in the amenity strong community of Ocean Pines.  Close distance to the Ocean City, Beach and Famous Boardwalk, so come and experience all the Entertainment and Amusement Parks that Ocean City, MD has to offer!  This Home is Bright and Cheerful, letting the sunshine in!   Open floor plan that enhances natural light with two sliders in the living area, and skylight. One slider leads to the three-season closed in Porch, and the other slider leads to the deck, perfect for entertaining and dining at home, or just enjoy a relaxing space to unwind.  Kitchen is equipped with stainless steel appliances, stunning custom cabinets with ample cabinet space, custom tile back splash, and recess lighting.  Custom flooring throughout.  Nautical themed decor and color palette enhance the beach vibes, and comfort.  Wood burning stove to keep you warm on the chilly nights.  Washer & Dryer.  Not to mention the Ocean Pines Community is located just minutes from Ocean City, Maryland and the BEACH! Ocean Pines Beach Club is right in the town of Ocean City direct Ocean front on 49th St. So, pack your beach bags, and spend the day at the beach... Beach Club offers community parking, outdoor pool, volleyball even a restaurant and bar.... AT THE BEACH! What more could you ask for? The Community is Packed with amenities... features indoor and outdoor community pools, Community Center, Recreation and Parks. Ocean Pines Yacht Club, and Golf Course. The Ocean Pines Community has a community Police Department, and Fire Department within the Community. Ocean Pines Public Library, and Ocean Pines Post Office. Grocery Store and The Manklin Creek Shopping Center within the community. If you are looking for convenience, and seeking a beach retreat, or a place to call home, look no further.... This is it! Don't let this one get away, live the life you deserve! Being sold furnished as seen, all decor and household items included.

31 Driftwood Ln, Berlin

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: Berkshire Hathaway HomeServices PenFed Realty - OP.

32 Driftwood Ln, Ocean Pines
$610,000
3 Beds ⋅ 2 Baths
Amazing Waterfront 3-Bedroom, 2-Bath Cottage in Ocean Pines Resort! Experience waterfront living at its finest in this charming 3-bedroom, 2-bath cottage featuring an expansive bulkhead with room for both your boat and Jet Skis. Whether you're heading out for a day on the water or enjoying the peaceful views from home, this property offers the perfect coastal lifestyle. The oversized rear deck and spacious backyard create an ideal setting for entertaining family and friends or simply relaxing while taking in the beautiful waterfront scenery. Inside, you'll find an updated custom kitchen complete with granite countertops, stainless steel appliances, and abundant custom cabinetry. Beautiful hardwood floors flow throughout the main level, leading to a spacious living room with a cozy wood-burning fireplace, built-in wood storage, and remarkable water views. The large dining area provides plenty of space for gatherings and is conveniently located adjacent to the kitchen. Step directly from the living room onto the expansive rear deck, where you can dine outdoors, entertain guests, or unwind while enjoying the tranquil waterfront setting. The main level also features a full bathroom, providing added convenience for family and guests. Upstairs features three well-appointed bedrooms, with the primary bedroom showcasing beautiful water views that provide a relaxing backdrop to start and end your day. Additional features include an attached garage and ample parking with a five-car driveway. Ideally located with easy access to the Saint Martin River and Isle of Wight Bay, this home is nestled within the sought-after Ocean Pines Resort community, offering the perfect combination of waterfront living, boating, fishing, and resort-style amenities. Don't miss this opportunity to own a beautiful waterfront retreat with direct water access and exceptional outdoor living. Schedule your private showing today!

32 Driftwood Ln, Ocean Pines

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: Atlantic Shores Sotheby's International Realty.

25 Seabreeze Rd, Ocean Pines
$350,000
3 Beds ⋅ 2 Baths
Welcome to 25 Seabreeze Road, an inviting three-bedroom, two bath home nestled in the amenity-rich community of Ocean Pines, where comfortable coastal living meets an exceptional lifestyle. With its Eichler-inspired mid-century modern influence, soaring wood-beamed cathedral ceilings, beautiful hardwood flooring, walls of glass, and a cozy wood-burning fireplace, this home offers architectural character, warmth, and everyday comfort. The spacious kitchen is thoughtfully designed with stainless steel appliances, including a new dishwasher, a double sink with a window view, and excellent storage. Just beyond the kitchen, you'll find a generous walk-in pantry complete with a standalone freezer, providing abundant space for everyday living and entertaining. Adjacent to the kitchen is a bright flex space enclosed by a wall of glass, ideal as a home office, reading nook, hobby room, or additional sitting area. The primary suite offers a private bath, while two additional bedrooms provide comfortable accommodations for family and guests. Outdoor living is equally enjoyable with multiple decks perfect for relaxing, dining, or entertaining. A detached one-car garage and an exterior storage room offer additional convenience and functionality. Living in Ocean Pines means enjoying one of the Eastern Shore's most desirable communities. Residents have access to an impressive array of amenities, including five swimming pools (indoor and outdoor), the Robert Trent Jones Sr.-designed Ocean Pines Golf Club, a full-service yacht club and marina, waterfront parks, tennis and pickleball courts, playgrounds, walking and biking trails, a community center, farmers markets, and year-round activities and events. The Beach Club in nearby Ocean City provides oceanfront dining and exclusive beach access, making every day feel like a vacation. Whether you're searching for a full-time residence, a weekend getaway, or an investment opportunity, 25 Seabreeze Road offers the perfect blend of comfort, convenience, and the unmatched lifestyle that Ocean Pines is known for.

25 Seabreeze Rd, Ocean Pines

Listing courtesy of Northrop Realty. Contact:

Selling Office: Coastal Life Realty Group LLC.

306 Ocean Pkwy, Ocean Pines
$285,000
3 Beds ⋅ 2 Baths
ANOTHER NEW PRICE! This home has many special features and is ready for immediate occupancy. This 3-bedroom and 2 full bath raised rancher has a big back enclosed porch, a front enclosed porch and two decks- one in the front and 1 in the back. It has an unfinished basement for storage and a single car garage on the ground level. New roof in the last 20 years and a new H/P. Newer cabinets and flooring in kitchen and dining area. There is a central vacuum system. Lots of storage space under the house. Gas fireplace in the spacious Living Room and a few steps up to the dining room and kitchen. Laundry room has the access door to the garage and basement storage areas. Walking distance to White Horse Park for the playground, Farmer's Market on Saturdays, Gift Shop or outdoor concerts. Easy walk to the Swim and Raquet Club complex with pool and bay access with beach and docks, tennis courts and walking trail. Easy to see. Seller says bring all offers.

306 Ocean Pkwy, Ocean Pines

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

Selling Office: Coldwell Banker Realty.

88 Newport Dr, Ocean Pines
$825,000
3 Beds ⋅ 3 Baths
Don’t Miss your Chance to enjoy the BEST panoramic Canal and Golf Course Views in Ocean Pines!!! The extra large, rear deck and fully screened porch offer unobstructed scenic views. There are roll-down sunshades on the screened porch, and beautifully landscaped grounds with irrigation, paver walkways, and a private boat dock with lift. Brand new stainless steel appliances, single basin sink, quartz countertops, and Fabuwood cabinets highlight the welcoming kitchen. The living room features a beautiful corner-set gas fireplace and built-in display storage shelving. Real bamboo hardwood flooring accents all living areas and bedrooms, while porcelain tile is found in the foyer, kitchen, and baths. All three bathrooms have been tastefully updated, while all bedroom closets have built-in organizers and lighting. In the garage with extra-tall ceiling height, you will find lots of cabinet storage, work surface, and a utility sink. A brand new dehumidifier was recently installed in the crawlspace, a whole house carbon water filtration system is included, and the 2 x 6 wall studs offer strong construction and deeper window sills throughout. Six vehicles will fit nicely in the thoughtfully designed driveway. There are so many more upgrades to discover in this home, located on a wide street in a quiet and lovely neighborhood!!

88 Newport Dr, Ocean Pines

Listing courtesy of Hileman Real Estate-Berlin. Contact:

Selling Office: Coldwell Banker Realty.

62 Newport Dr, Ocean Pines
$354,900
3 Beds ⋅ 2 Baths
Swiss Chalet charm meets modern coastal living at 62 Newport Dr Ocean Pines Md A turn key newly renovated retreat over looking the fourth hole of the famous Robert Trent Jones championship golf course! Beautifully maintained and cared for. With refreshed photos take another look At 62 Newport Dr and the total renovation of this home. It is ideal for a primary residence, a weekend beach-golf escape , or a smart rental investment. When you walk in, the main level features a charming open floor plan with new vinyl plank flooring and an updated kitchen with beautiful stainless steel appliances and new stackable washer and dryer for convenience.The living area has an electric fireplace creating a warm inviting focal point beneath the vaulted ceiling which now includes a new light fixture and a stylish ceiling fan for comfort and ambiance. Two comfortable bedrooms and a full bath on the main level offer flexibility for guests, a home office, or den , all with brand new carpeting , painted throughout with new trim and new 6 panel doors. The upstairs loft features a primary bedroom and full bath with its own Mitsubishi mini split for climate controlled living space. Carpet was installed inside and on the stairs. Over the past four years this home has been completely renovated, including new HVAC system, new thermal pane windows, Doors and updated vinyl siding. Gutters with leaf filters. The roof is from 2018.New plumbing, Hot water heater and updated electric. The house has a whole water filtration system. The crawl space was partially encapsulated and a new sump pump and dehumidifier were added for climate control. Enjoy peaceful mornings and breezy evenings on the screened in porch taking in views of the golf course among the mature trees of Ocean pines The yard was opened up and installed with new stone and pavers around both front and side yards for easy walking and low maintenance living. Brand new scalloped fencing around the perimeter of the backyard to keep your loved ones safe and secure. There is also room for a small shed in the backyard. The cement driveway holds up to 5 cars which adds exceptional convenience for gatherings and guests and rental stays.The enclosed carport provides sheltered parking that has four electrical outlets suitable for future EV charging. There is also a nice size shed for storage as well as floored eaves for storage on 2nd floor. This Swiss Chalet style home is conveniently located in walking distance to White Horse Park, weekly Farmers market, play ground and the Ocean Pines Community Center, making everyday life and weekend enjoyment incredibly convenient. With its total renovation, golf course setting, walkable location, It is a strong potential as a getaway or income producing property. 62 Newport offers exceptional value at its new price. It’s a one of a kind architectural style and definitely stands out from the rest. Experience the comfort and ease and charm of Ocean Pines living!

62 Newport Dr, Ocean Pines

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

Selling Office: Coastal Life Realty Group LLC.

44 Grand Port Rd, Ocean Pines
$345,000
3 Beds ⋅ 2 Baths
BEST AND FINAL DUE BY 12:00pm MONDAY, JUNE 8th. Opportunity knocks at 44 Grand Port Rd! Offered as the lowest-priced waterfront property currently available in Ocean Pines, this 3-bedroom, 2-bath home is ready for its next chapter. Built as one of the first homes in Ocean Pines—reportedly the 11th home ever constructed in the community—this property offers a unique piece of local history along with tremendous potential for renovation or redevelopment. Conveniently located near the Swim & Racquet Club and situated on a desirable waterfront lot with easy boat access to the open bay and no bridges to navigate, the location is hard to beat. This is a true fixer-upper being sold strictly as-is and is ideal for investors, builders, or buyers looking to create their own waterfront retreat. Buyers are encouraged to perform their own due diligence and review the pre-home inspection report available in the documents section. Enjoy Ocean Pines amenities including pools, golf, parks, walking trails, pickleball and tennis courts, a yacht club, and beach club access. A rare opportunity to secure an affordable waterfront property in one of the area's most sought-after communities.

44 Grand Port Rd, Ocean Pines

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

Selling Office: Unrepresented.

21 Seabreeze Rd, Ocean Pines
$485,000
5 Beds ⋅ 3 Baths
Welcome to this spacious split-level home tucked away in the heart of amenity-rich Ocean Pines. The main living level offers an open-concept layout featuring a bright living room, dining area, and large kitchen with ample counter space—perfect for gathering, entertaining, or everyday living. This level also features a lovely sun porch and an outdoor deck, extending the living space outdoors. The upper level includes a generously sized primary bedroom with an en-suite bath, conveniently located near the main living areas. The lower level provides exceptional flexibility with four additional bedrooms, a full bath, laundry area, and a separate den with its own entrance—ideal for guests or extended living arrangements. Enjoy outdoor living with a welcoming front porch, surrounded by mature trees and coastal charm. Located just around the corner from the Ocean Pines Swim & Racquet Club, this home offers easy access to the community’s many amenities, including multiple pools, tennis courts, golf course, marinas, parks, walking trails, and the Ocean Pines Beach Club. With over 3,000 square feet of living space, this property is ideal for a large family, multi-generational living, or as a vacation home with strong short-term rental potential.

21 Seabreeze Rd, Ocean Pines

Listing courtesy of Keller Williams Realty Delmarva. Contact:

Selling Office: Berkshire Hathaway HomeServices PenFed Realty - OP.

48 Windjammer Rd, Ocean Pines
$380,000
3 Beds ⋅ 2 Baths
This inviting home in the highly desirable community of Ocean Pines offers the perfect blend of comfort, style, and convenience. Custom built by Groff for the original owners, this well-designed 3-bedroom, 2-bath residence features a spacious open floor plan that’s ideal for both everyday living and entertaining. Step inside to find a bright and airy layout, complemented by freshly painted bathrooms and a home that has been professionally deep cleaned—truly move-in ready and waiting for your personal touch. The main living areas flow seamlessly together, creating a welcoming atmosphere for gatherings. One of the standout features is the expansive rear porch, (approx. 300 sq, ft.) accessible through double doors from the dining area, living room, and primary bedroom—perfect for indoor-outdoor living and hosting guests. Major updates, including a newer roof and HVAC system, provide added peace of mind. The property also includes an oversized garage of approximately 460 square feet, offering ample space for parking, storage, or a workshop. Outside, the partially fenced backyard provides a great space for pets, play, or relaxation. This home is a wonderful opportunity to enjoy all that Ocean Pines has to offer—don’t miss your chance to make it yours! Home is being sold AS IS!

48 Windjammer Rd, Ocean Pines

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

Selling Office: Coldwell Banker Realty.

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