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$1,300,000
4 Beds ⋅ 3 Baths
Waterfront Home in Terns Landing – Ocean Pines 2nd lot in from the end of the canal wiwth Bay Views Welcome to this beautiful 4-bedroom, 2.5-bath waterfront home located in the highly sought-after Terns Landing section of Ocean Pines. Designed with an open and airy layout, this home features floor-to-ceiling windows that fill the space with natural light from nearly every angle, creating a bright and inviting atmosphere throughout. The spacious kitchen is highlighted by granite countertops, perfect for both everyday living and entertaining. Just off the main living area, step out onto the extra-large deck overlooking the canal, where you’ll enjoy peaceful water views and stunning vistas of the Isle of Wight Bay. The second-floor loft offers additional living space, ideal for a home office or lounge area, while the generously sized game room provides flexibility and could easily serve as a 5th bedroom. A convenient 2-car garage adds to the home’s functionality. Major updates include a bulkhead less than 10 years old, a brand-new roof (2026), and a new driveway (2025), offering peace of mind for years to come. Enjoy all the benefits of this amenity-rich community, ideal for year-round living or as a second home getaway. With everything Ocean Pines has to offer, this is a rare opportunity you don’t want to miss! This home was built above mean High Tide and to Florida Hurrican Code. Schedule your showing today—this one won’t last long! Property is being Sold “As Is” Seller and has included a 1 year Home Warranty. The second floor AC is now brand new just install 9/10/26

24 Stacy Ct, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211
$349,900
2 Beds ⋅ 2 Baths
Enjoy easy one-level living in this charming 2-bedroom, 2-bath rancher located in the sought-after community of Ocean Pines. The functional floor plan offers comfortable living spaces, abundant natural light, and low-maintenance living—perfect as a primary residence, vacation getaway, or investment property. Large deck with storage shed attached. Ocean Pines residents enjoy an exceptional lifestyle with outstanding amenities, including indoor and outdoor swimming pools, tennis courts, scenic walking and biking paths, a dog park, community center, playgrounds, parks, and year-round activities. Conveniently located just minutes from Ocean City beaches, shopping, dining, golf, and marinas, this home offers the perfect blend of comfort, recreation, and coastal living.

170 Windjammer Rd, Ocean Pines

Listing courtesy of Coldwell Banker/Bud Church Rea. Contact: (410) 524-7888
$590,000
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. Recently updated crawl space encapsulation and dehumidifier ensure peace of mind. 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
$339,000
4 Beds ⋅ 3 Baths
Welcome to 205 6th Street in Pocomoke City! This beautifully renovated home was completely updated from top to bottom in 2022 and is truly move-in ready. This property offers a fantastic opportunity as a primary residence, vacation getaway, or investment property. Recent improvements include a new driveway, sump pump, dehumidifier, fully fenced backyard, and a newly added patio—providing peace of mind and the perfect space for outdoor entertaining and relaxation. Conveniently located just 30 minutes from Berlin and within easy reach of Virginia's Eastern Shore, you'll enjoy small-town charm with quick access to beaches, shopping, dining, and outdoor recreation. Don't miss your chance to own this beautifully updated home—schedule your private showing today!

205 6th St, Pocomoke City

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400
$2,795,000
5 Beds ⋅ 6 Baths
Welcome to 12355 Southampton Drive, the crown jewel of Lighthouse Sound, one of the Eastern Shore's most prestigious waterfront golf communities. This is a rare opportunity to own arguably the finest homesite in the neighborhood, where this extraordinary custom residence captures sweeping panoramic views of Assawoman Bay and the sparkling Ocean City skyline from nearly every rear-facing room. A dramatic two-story foyer with a graceful curved staircase sets the tone, drawing your eye straight through the soaring great room to the breathtaking water beyond. The two-story family room is anchored by a stunning natural stone fireplace with gas insert, creating an unforgettable gathering space framed by walls of glass. Designed for both everyday living and effortless entertaining, the chef's kitchen features gas cooking, granite countertops, a large center island, breakfast bar, sunny dining nook, walk-in pantry, and a fully equipped butler's pantry complete with wet bar and sink. Every space is thoughtfully connected to the expansive rear decks, ensuring the spectacular views are always part of the experience. The luxurious first-floor primary suite is a true private retreat, offering direct deck access, uninterrupted bay views, two professionally organized walk-in closets, and a spa-inspired bath with dual vanities, soaking tub, and oversized walk-in shower. A private study, spacious dining room, and main-level laundry complete the first floor. Upstairs, an impressive open landing overlooks the great room below and leads to four generously sized guest suites, each with private vanity and dressing areas and convenient en-suite bath access, providing exceptional comfort for family and guests alike. The outdoor living is every bit as remarkable as the interior. Nearly 1,700 square feet of wraparound Trex decking spans the rear of the home across two levels, creating an unparalleled setting for morning coffee, sunset cocktails, entertaining under the stars, or relaxing around the fire pit while watching boats drift across the bay and the Ocean City skyline come alive each evening. During the summer, enjoy a front-row seat to the free fireworks display every Sunday evening, launched from Northside Park just across the bay, a spectacular tradition that can be enjoyed from the comfort of your own deck. Additional highlights include Brazilian cherry hardwood flooring throughout, an oversized three-bay garage with abundant storage for vehicles and water toys, recessed lighting, ceiling fans, and quality craftsmanship throughout. Residents of Lighthouse Sound enjoy championship golf, an elegant clubhouse, dining, and one of the most spectacular waterfront settings on Maryland's Eastern Shore. Luxury. Views. Lifestyle. Rare opportunity. This isn't simply a home, it's a front-row seat to one of the most breathtaking waterfront panoramas on the East Coast. Once you experience the views from 12355 Southampton Drive, everywhere else feels ordinary.

12355 Southhampton Dr, Bishopville

Listing courtesy of Northrop Realty. Contact: (302) 539-0800
$239,900
3 Beds ⋅ 2 Baths
Charming and well-maintained older 3-bedroom, 2-bath home in Pocomoke City offering classic character with thoughtful updates. This move-in ready home features hardwood flooring throughout, a welcoming layout, central air conditioning, and a kitchen with new appliances and upgraded countertops. Washer and dryer are included for added convenience. Other recent improvements include replacement windows and encapsulated crawl space. Enjoy a private backyard perfect for relaxing, entertaining, or gardening. Detached garage Conveniently located near schools, parks, shopping, downtown and the scenic Pocomoke River. A wonderful opportunity for first-time buyers, downsizers, or anyone looking for comfort, charm, and convenience.

201 6th St, Pocomoke City

Listing courtesy of Hall Realty. Contact: 4104302000
$550,000
3 Beds ⋅ 3 Baths
Welcome to 10541 Shady Drive in Berlin, a private Eastern Shore retreat offering an incredible opportunity as a primary residence, vacation getaway, or potential short-term rental. Surrounded by mature trees, this spacious home features multiple living and entertaining areas, hardwood floors, abundant natural light, a generous kitchen, cozy wood-burning stoves, and a game room with a pool table—providing plenty of space for family and guests to relax and enjoy. Outside, the private swimming pool and expansive deck create the perfect vacation-style setting for summer days, outdoor dining, and entertaining. Conveniently located near Berlin and within easy reach of Ocean City, beaches, dining, shopping, and area attractions, this property has all the ingredients for an exciting Airbnb or vacation-rental opportunity. Whether you’re looking for your own Eastern Shore escape or an investment property with guest-friendly amenities, Shady Drive is ready for your vision.

10541 Shady Dr, Berlin

Listing courtesy of KW Metro Center. Contact: (703) 564-4000
$1,375,000
4 Beds ⋅ 4 Baths
Original lot for Boise Cascade to promote Ocean Pines from their sales center when it was first being developed. The original house was torn down and this lovely home eminates the spirit of Ocean Pines! Located on a wide canal with gorgeous evening sunsets will captivate you. The beautiful, open, floorplan is a must see... great for entertaining and admired by family and friends. There is close access to the Assawoman Bay and the Swim and Racket Club. The primary suite is on the main level with it's own private bath.

13 Widows Watch Ct, Ocean Pines

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

$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
$1,699,000
5 Beds ⋅ 5 Baths
Professional Pictures are coming soon! Nestled in the exclusive bayfront enclave of Bay Point Plantation, this beautiful coastal residence epitomizes luxury living, offering spectacular views of the Ocean City skyline. Built with intention for energy efficiency in 2011 featuring three separate Geothermal HVAC systems, this detached architectural masterpiece boasts over 4,500sqft with five spacious bedrooms and four full bathrooms with a 5th bathroom fully plumbed-in for future installation. Step inside to discover an expansive open floor plan that invites natural light to dance across the room from the floor-to-ceiling glass sliders that illuminate the natural beauty of Turville Creek with panoramic views of Ocean City's High Rise Row as its backdrop. The heart of the home is the gourmet kitchen, featuring an eat-in area perfect for casual dining, while the adjacent living spaces are enhanced by an elegant gas fireplace, creating a warm and inviting atmosphere for gatherings. Adjoining the primary living area is a 19'x19' sunroom with cathedral ceilings, built-in cabinets for entertaining, featuring its own geothermal HVAC system. The balloon framed sunroom, featuring magnificent views of Turville Creek and the OC skyline, was framed and designed ready to drop in an in-line Swim Spa with the concrete pad and electric in place. Just off the sunroom, a brand new, expansive TimberTech deck was just installed in 2026 featuring low-voltage landscape lighting which leads down to a huge flagstone patio area for additional outdoor living and entertainment space. The Primary Suite, a true entry-level sanctuary, offers breathtaking bay views and is complemented by a Master Bathroom offering a Whirlpool Tub and ceramic tiled Rainforest ceiling shower, a spacious walk-in closet, plus an additional Half Bath with its own walk-in closet. A second entry-level bedroom with the plumbing for a future full bathroom is currently situated as an office. The stairway of the home leading to the second floor wraps around a space designed for a future elevator addition with a 6" concrete pad, electric and phone line already in place. The second floor offers an additional three bedrooms with two full baths and a large Bonus Room with its own fireplace, tv mount and surround sound speaker wiring. Traverse up to the cupola for a serene retreat setting, ideal for an intimate seating area to take in the spectacular, surrounding water views and the renown Golden Hour that illuminates Ocean City's skyline with rainbow hues each evening. Every detail of this home has been meticulously designed, from the recessed lighting that highlights the home's architectural features to the exterior landscape lighting that creates ambiance for every occasion. The convenience of a main floor laundry room just off the four-car garage adds to the home's thoughtful design, while the Fire Department Knox Box provides peace of mind. Enjoy the tranquility of the tidal wetland surroundings, where nature's beauty is just outside your door here on Plantation Lane. As part of a prestigious gated community, residents enjoy exclusive access to a marina club, pier, and dock, perfect for boating enthusiasts or for crabbing, fishing and sightseeing. This luxurious residence is not just a home; it's a lifestyle choice that offers the perfect blend of comfort, elegance, and natural beauty. Experience the ultimate in coastal living, where every day feels like a vacation.

10316 Plantation Ln, Berlin

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400
$495,750
3 Beds ⋅ 2 Baths
Welcome to 400 136th Street. Corner lot in Caine Woods right across the street from Gorman Park with Playgrounds,tennis & Pickle ball. 3 Bedrooms 2 full baths with a wide open floor plan. Large Kitchen with pleanty of cabinets for storage. Nice enclosed florida room off the Dining room. Walking distance to the beach and the City Bus . Come check out this property today .

400 136th St, Ocean City

Listing courtesy of Larry Holdren Real Estate Inc. Contact: 4102502700
$775,000
4 Beds ⋅ 4 Baths
11635 Maid At Arms Lane is a 4-bedroom, 3.5-bath home with paid-for solar panels, located in GlenRiddle, a premier gated waterfront community with a boat ramp, marina, golf, and resort-style amenities. A welcoming front porch and dramatic two-story foyer create an impressive first impression, featuring transom windows and an architectural landing ideal for displaying art, greenery, or decorative pieces. Designed for modern living and easy entertaining, the main level offers an open-concept layout connecting the kitchen, dining area, and spacious two-story great room. Abundant natural light, hardwood floors throughout the entire home, crown molding, soaring ceilings, floor-to-ceiling windows, and a gas fireplace add warmth and architectural interest to the main living space. The kitchen features upgraded countertops, two wall ovens, gas cooktop, stainless appliances, and generous cabinet space. Just off the dining area, sliding doors lead to the first-floor screened porch, extending the living space for relaxing, dining, or entertaining while overlooking a peaceful backyard with open lawn space and a backdrop of mature trees that adds privacy, natural beauty, and a serene sense of retreat. A standout feature is the main-level bedroom layout, offering two first-floor bedrooms, each with its own en suite full bathroom. The generously sized first-floor primary suite includes a walk-in closet with custom built-ins and a private bath with double vanity, jetted tub, fully tiled walk-in shower, and separate water closet. The second first-floor bedroom includes a closet with custom built-in cabinetry and an attached en suite full bathroom, offering flexibility for guests, extended stays, an office, den, or multigenerational living. A separate half bath is also located in the hallway, and the first-floor laundry room adds everyday convenience. Upstairs, the spacious loft is divided into two flexible sections, creating the opportunity for multiple uses such as a home office and reading nook, study area and media lounge, playroom and craft space, fitness area and library, or a quiet retreat separate from the main living level. The upper level also includes two additional bedrooms connected by a Jack-and-Jill full bath, including a larger bedroom with a double-door closet and another bedroom with a walk-in closet and Palladian windows. Additional highlights include a full 2-car garage with elevated mechanical systems and an epoxy-painted floor designed for durability, easy maintenance, and a showroom-style finish; dual-zoned heating and air conditioning with Nest thermostat systems for remote control, scheduling, and energy-saving automation; electric central air; main-level gas furnace; second-level electric heat pump; gas hot water heater; and owned solar panels. Because the solar panels are paid for, the new homeowner can benefit from improved energy efficiency and potential utility cost savings without assuming a solar lease or payment contract. The solar panels also include approximately 12 years remaining on the transferable warranty. The home’s location within GlenRiddle is especially appealing, positioned a short distance from many of the community’s most popular amenities, including the clubhouse, outdoor pool, fitness center, and tennis courts. GlenRiddle also offers on-site property management, a boat ramp, marina, two championship golf courses, and Ruth’s Chris Steak House located within the community. Enjoy convenient access to Ocean City beaches, Assateague Island, historic downtown Berlin — known as America’s Coolest Small Town — TidalHealth services, shopping, dining, and everyday conveniences.

11635 Maid At Arms Ln, Berlin

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 4105247000
$214,900
3 Beds ⋅ 2 Baths
Welcome to 811 Market Street, a charming and well-maintained 3-bedroom, 1.5-bath home offering a blend of character, comfort, and valuable updates. Major improvements have already been completed, including a new hot water heater in 2024, while the roof, HVAC system, windows, kitchen countertops, and bathroom countertops were updated in 2015, providing peace of mind for years to come. The main level features inviting living and dining spaces filled with natural light, along with a functional kitchen designed for everyday living and entertaining. Upstairs, three comfortable bedrooms , complemented by a full bath. Additional storage and utility space enhance the home's practicality. Outside, the yard provides room to relax, garden, or enjoy outdoor gatherings. Located in the heart of Pocomoke City, this home offers convenient access to local shops, restaurants, and everyday services, while nearby attractions such as the scenic Pocomoke River, Cypress Park, and the Delmarva Discovery Museum provide endless opportunities for recreation and exploration. Commuters will appreciate easy access to Routes 13 and 113, connecting to Salisbury, Chincoteague Island, and Maryland's Atlantic beaches. Combining important system updates, comfortable living spaces, and a convenient location, this property presents an excellent opportunity to enjoy all that Maryland's Eastern Shore has to offer.

811 Market St, Pocomoke City

Listing courtesy of Redfin Corp. Contact: 3016586186
$3,599,000
6 Beds ⋅ 8 Baths
ONCE UPON A TIME in a sweeping coastal vista with an architectural world-class design, there is a TIMELESS, premiere Lighthouse Sound estate. Truly an unparalleled level of both privacy and prestige. Fashioned in the classic Shingle-Style design, otherwise known as "Coastal Seaside Architecture"... MANY EXPENSIVE HOMES ARE LARGE, BUT FEW EXPENSIVE HOMES ARE PROPORTIONED THIS WELL. The symmetry here creates a feeling of both permanence and luxury. The (installed summer 2026) roof is exceptionally interesting with its multiple gables that adds both character and ceiling height inside. Copper accent roofs feature standing seams. The rooftop Widow's Watch, or observation deck, (OR crow's nest!) is an amazing feature- especially when YOU are up there taking a good look at the 360-degree views of the bay, or fireworks displays, or enjoying your favorite beverage. All rooms in this house feature exquisite hand-crafted architectural elements and views of the natural, coastal habitats. Enter into the main hall and your eyes will be immediately drawn to the direct view of the water. ** Moving forward into the LIVING ROOM, or great hall, is a complete wall of windows soaring 20 feet high. An aged-glass mirror adorns the limestone woodburning fireplace beneath. (mirror included) Most of the floors throughout are walnut, finished on site and stained. (Refinished July 2026!) **The BILLIARD ROOM and adjoining den/MEDIA ROOM showcases brilliant walls of Honduran mahogany. A solid wood pocket door separates the two rooms, if desired. A full wet bar area with granite counters grace the side of the billiard room, including an under counter fridge. Adjoining the billiard room is a side porch with a "cat-slide" roof, adding yet additional character to the overall design. Speaking of design, the Becker-Morgan Group in Salisbury, MD were the architect engineers of this project along with collaboration from both Washington, D.C. And New York City design teams. The **DINING ROOM displays custom wallpaper that was hand painted and depicts the natural elements and scenes from the ponds and surrounding environments. The dining room features a grand bay window, framing magnificent sunsets for guests to admire. **The chef-inspired KITCHEN is appointed with premier Wolf appliances and striking Carrara Italian marble. It features an exquisite copper tile backsplash framing the six-burner gas range and griddle, complemented by an integrated, refined sitting area for elegant entertaining. The floor is limestone from Paris Ceramics. Color is called Irish Blue but shows as black. **A BUTLER'S PANTRY offers granite counters, a 120 bottle wine refrigerator, a copper sink and a beverage refrigerator. The three-story TURRET overlooks the gated 40 X 16 heated swimming pool and hot tub. First floor of the turret is a wonderful and bright SUNROOM, while the second level of the turret is the YOGA ROOM located next to the immense PRIMARY BEDROOM SUITE that features a sprawling "dressing room", or could easily be converted into a nursery. The primary bedroom features a gas fireplace plus an additional adjoining sitting room overlooking the bay and offers access out to the private primary bedroom's balcony. The PRIMARY BATH features marble counters, Thassos 12 X 12 white natural marble floor, quarried in Greece, and the third floor of the turret showcases an office tower/observatory/office. INCREDIBLE architecture and INCREDIBLE views from this 1.47 acre lot! There are SO MANY additional custom features in this spacious home, we've added a special list for you to review upon your request. Although encompassing more than 8,200 square feet, this storybook waterfront residence is gracious in scale but intimate in how it lives. Rarely will you ever find such an enchanted home to call your own. Here's your opportunity to LIVE HAPPILY EVER AFTER. **Current furnishings and décor may differ from those shown in the photographs.

12353 Southhampton Dr, Bishopville

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 3025372616
$99,900
4 Beds ⋅ 2 Baths

810 2nd St, Pocomoke City

Listing courtesy of Coldwell Banker Realty. Contact: 3025391777
$579,000
3 Beds ⋅ 2 Baths
Welcome to this beautifully remodeled 3-bedroom, 2-bathroom rancher situated on nearly a half acre of land in the heart of historic Berlin, Maryland, without the burden of HOA fees! Thoughtfully updated from top to bottom, this one-story home with a basement combines modern finishes and conveniences with the comfort and functionality of single-level living. Step inside to discover bright, inviting living spaces designed for everyday living and entertaining alike. The spacious layout flows seamlessly from room to room, creating a warm and welcoming atmosphere throughout, while the basement provides additional storage, workspace, or future possibilities to suit your needs. Outside, the expansive lot offers endless opportunities for gardening, outdoor gatherings, recreation, or simply enjoying the privacy and open space! Located just steps from Berlin?s award-winning Main Street, you'll enjoy easy access to charming boutiques, local restaurants, coffee shops, parks, and year-round community events. Whether you're searching for a primary residence or a weekend getaway near the beaches of Ocean City and Assateague Island, this move-in-ready home offers the perfect blend of location, convenience, and small-town charm. Don't miss this rare opportunity!

100 Esham Ave, Berlin

Listing courtesy of Coastal Life Realty Group LLC. Contact: (443) 235-8382
$575,000
6 Beds ⋅ 2 Baths
Welcome to this beautifully maintained Victorian in the heart of historic Berlin, also known as America's Coolest Small Town. Offering 6 bedrooms, 2 full bathrooms, and a flexible floor plan, this home combines timeless character with thoughtful updates and modern conveniences. A spacious wrap-around porch welcomes you inside complete with an enclosed sleeping porch, where a grand foyer showcases a stunning stained-glass window, hardwood flooring, soaring ceilings, and classic architectural details throughout. The updated kitchen features Corian countertops, maple cabinetry, stainless steel Jenn-Air appliances, and durable flooring, while the formal dining room, living room, and sunroom provide plenty of space for gathering and entertaining. A dedicated home office offers an ideal work-from-home setup, and a versatile sitting room provides additional space that can be tailored to your needs. Recent improvements include updated electrical and plumbing systems, a newer roof, and numerous enhancements throughout the property. The detached garage offers endless possibilities as a workshop, hobby space, recreation space, or additional storage. French doors open to a large rear deck overlooking the spacious backyard, creating the perfect setting for outdoor entertaining, relaxing, or enjoying time with family and friends. Located just a couple of blocks from Berlin's vibrant downtown shops, restaurants, and community events, and only minutes from Ocean City, this property offers the charm of small-town living with convenient access to the beach and coastal attractions. A rare opportunity to own a home filled with character, space, and modern updates in one of Maryland's most sought-after communities.

207 Williams St, Berlin

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$974,900
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
$869,900
5 Beds ⋅ 3 Baths
68.48 Acres with Custom Home & Premier Hunting Habitat This exceptional 68.48-acre property features a 3,369 sq ft, 5-bedroom 2.5 bath home built in 2010, offering the perfect blend of comfort and outdoor living. In the ariels you will see the ground tilled up around the house, where the owner plants a sunflower field. Designed with the avid outdoorsman in mind, the land is thoughtfully managed for wildlife habitat and hunting. The property is encumbered by a MALPF easement and enrolled in CREP, preserving its natural beauty while supporting diverse ecosystems. Multiple established lanes, stands, and box blinds are already in place, creating turnkey opportunities for deer and turkey hunting throughout the property. Approximately one-third of the way into the tract, an impoundment enrolled in CREP offers excellent potential for waterfowl habitat—with minor improvements, it could be transformed into a productive duck impoundment. There are two box blinds, two ladders, and 3 feeders that convey with the property. Midway through the property, a power line corridor—intentionally excluded from easements—provides an ideal location for planting food plots to further enhance wildlife activity. At the rear of the property, there is a pond that attracts wood ducks and adds to the land’s recreational and ecological value.  Whether you're looking for a private hunting retreat, a conservation-focused investment, or a peaceful homestead surrounded by nature, this property offers a rare opportunity to own a well-managed piece of land where wildlife thrives.

2435 Payne, Pocomoke City

Listing courtesy of The Land Group. Contact: (410) 934-3478
$329,000
3 Beds ⋅ 3 Baths
OWNER FINANCING AVAILABLE!!! This beautifully remodeled 3-bedroom, 2.5-bath home offers the perfect blend of modern convenience and classic charm. Thoughtfully updated while preserving the character and warmth of the original home, this property provides a welcoming atmosphere from the moment you arrive. The heart of the home features a brand-new kitchen with stylish cabinetry, updated countertops, and new appliances, making it ideal for both everyday living and entertaining. The bathrooms have also been tastefully renovated with modern finishes and fixtures. Outside, you'll find a spacious backyard retreat complete with a charming gazebo, perfect for relaxing, hosting gatherings, or enjoying peaceful evenings outdoors. With its combination of updated amenities and preserved architectural character, this home is truly the best of both worlds, Seller might consider owner financing. Don't miss the opportunity to make this move-in-ready gem your own!

807 Market St, Pocomoke City

Listing courtesy of Decatur Byrd Realty. Contact: (410) 957-2220
$99,900
4 Beds ⋅ 2 Baths
Investor special with major upside potential in the heart of Pocomoke City! This partially renovated 4-bedroom, 2-bath Colonial offers approximately 1,760 square feet of living space and sits on a generous quarter-acre lot. Renovations have already been started, providing a valuable opportunity for investors, contractors, flippers, or buyers looking to complete a project and build equity. Recent improvements and visible progress throughout the home create a solid foundation for the next owner to bring their vision to life. Located within city limits with public water and sewer, this property offers convenient access to downtown Pocomoke City, local shopping, restaurants, schools, and major routes. The spacious floor plan, large rooms, and classic Colonial architecture make this an attractive candidate for a fix-and-flip, long-term rental investment, short-term rental opportunity, or owner-occupant renovation project. Properties with this level of potential at this price point are becoming increasingly difficult to find. Sold strictly As-Is. Cash, renovation financing, or private financing may be best suited. Bring your contractor, imagination, and investment strategy to unlock the full value of this promising Worcester County property.

808 2nd St, Pocomoke City

Listing courtesy of Coldwell Banker Realty. Contact: 3025391777
$398,999
3 Beds ⋅ 2 Baths
Welcome to The Blue Crab Beach House, where coastal charm meets comfort and convenience. Nestled in one of the area's most sought-after communities, you'll enjoy access to resort-style amenities including pools, golf courses, a marina, and nearby beaches—all while being just minutes from shopping, dining, and entertainment. Inside, an open and inviting floor plan creates the perfect setting for both entertaining and everyday living. The main level offers the ease of single-floor living with a spacious primary bedroom, full bathroom, and laundry area. Upstairs, two additional bedrooms share a convenient Jack-and-Jill bathroom, providing plenty of space for family and guests. Step outside and embrace the coastal lifestyle. Start your mornings on the peaceful porch with a cup of coffee, then spend afternoons and evenings enjoying the spacious yard—ideal for games, gatherings, barbecues, and outdoor relaxation. Recent updates provide added value and peace of mind, including: New roof (2023) Fresh interior paint throughout New bedroom light and ceiling fan fixtures Brand-new dishwasher (November 2024) New microwave (March 2025) Newer kitchen appliances Unique features such as custom-built loft twin beds and a cozy wood-burning stove add warmth, character, and charm to this special home. Whether you're searching for a full-time residence, vacation getaway, or investment opportunity, The Blue Crab Beach House offers the perfect blend of tranquility, recreation, and coastal convenience. Come experience the best of beach-area living.

3 Starboard Ct, Ocean Pines

Listing courtesy of Newport Bay Realty. Contact: 4102137040
$432,500
4 Beds ⋅ 2 Baths
Located on the eighth fairway of the Ocean Pines Robert Trent Jones Golf Course in sought-after Bay Colony, this exceptional retreat features an open floor plan with cathedral ceilings, skylights, hardwood flooring in the main living areas, and a family room wood burning fireplace, equipped with screen and fireplace tools. The four-bedroom two-bath rancher style home with an open area concept in the kitchen, living and dining rooms. The family and dining room have open access to the Florida four-season sunroom. There is a separate screened in porch creating seamless options for year-round enjoyment. This beautiful home has been updated with a new roof in December 2025 with a 20-year transferrable warranty and sky lights and new gutters with a 5-year warranty, and primary bedroom bathroom upgrade. The Heating Ventilation and Cooling system was replaced in 2016, and the beautifully refinished kitchen is appointed with new cabinetry, and modern appliances with abundant workspace for effortless entertainment. Additional highlights include a separate shed with plentiful storage room and an extra-large concrete driveway with room for six cars. There is plenty of street parking as well. Outside, beautifully shaded landscape with shuffleboard structures in the front and a deck and firepit in the back yards looking out over the golf course. Furnishings can be purchased separately. Community boat ramps exist to launch your personal watercraft. The launch areas have direct access to bay and ocean waters. Boating, fishing, crabbing, and clamming to easy access to the Ocean Pines yacht club, golf course, clubhouse grill, pools, racquet facilities, Ocean City beach club and more are all a part of living in Ocean Pines. The Ocean Pines Beach Club is located between 49th and 50th streets with private parking, pool and changing area flowing out to the beach on the Atlantic Ocean.

48 Battersea Rd, Ocean Pines

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$949,750
5 Beds ⋅ 5 Baths
New Price Improvement-OVER 5,400 SQUARE FEET OF FINISHED LIVING SPACE! If space, flexibility and the GlenRiddle lifestyle are on your wish list, 11436 Maid at Arms Lane deserves a closer look. Offering an impressive 5 bedrooms, 4.5 baths and approximately 5,404 finished square feet across three levels, this exceptional home delivers an amount of living space that is increasingly difficult to find. Perfectly positioned within the gated GlenRiddle community, the home enjoys desirable southern exposure across the rear, golf course views and water views toward Turville Creek from the front. An impressive bank of windows fills the expansive living areas with natural light while showcasing the surrounding scenery. At the heart of the home is a spacious gourmet kitchen designed for everyday living and entertaining. Generous countertop and preparation space, abundant cabinetry and two walk-in pantries provide exceptional storage and functionality. The open floor plan flows into oversized gathering and entertaining areas, giving everyone room to spread out while maintaining a comfortable connection between spaces. One of the home’s greatest advantages is its incredibly flexible three-level floor plan. Two private en-suite bedrooms, one on the second level and another on the third, provide excellent accommodations for owners, family and overnight guests. With five bedrooms and more than 5,400 finished square feet, there is tremendous flexibility for home offices, fitness space, media or game rooms, guest accommodations and additional living areas. The oversized two-car garage provides additional storage and features dual 220-volt outlets for EV charging. Rough-in closets on each level also provide infrastructure for the potential addition of a future elevator. Living in GlenRiddle is about more than the home. Enjoy an amenity-rich gated community featuring a marina, community pool, clubhouse, fitness center, tennis, golf, walking and jogging paths and Ruth’s Chris Steak House. Golf-cart-friendly surroundings make it easy to enjoy everything the community has to offer, while the beaches, restaurants, shopping and entertainment of Ocean City are just minutes away. With approximately 5,404 finished square feet, five bedrooms, multiple en-suite accommodations, golf and water views, southern exposure and an outstanding GlenRiddle location, 11436 Maid at Arms Lane offers an exceptional combination of SPACE, LOCATION and LIFESTYLE. If you have been searching in the Ocean City and West Ocean City area and want substantially more room without sacrificing proximity to the beach, put this home on your must-see list. (rough-in closets for future elevator on every floor)

11436 Maid At Arms Ln, Berlin

Listing courtesy of Keller Williams Realty. Contact: steve@srarealty.com
$369,900
3 Beds ⋅ 2 Baths
Motivated sellers just made another a price reduction! All spruced up and ready to go! Fresh paint and new carpet throughout this 1 level contemporary coastal custom-built 3-bedroom 2 bath home in the community of Ocean Pines. Delightful 14 x 12 screened porch plus a 12 x 12 deck for enjoying the good life here at the beach. Spacious Primary bedroom with a vaulted ceiling has a walk-in-closet and access to the primary bath with a walk-in shower. 8x7 attached shed for all you bike, lawn equipment and beach toys. Gutter guards installed. Asphalt paved driveway for plenty of parking for you, family and friends. 5 x7 laundry room with washer and dryer. HVAC is approximately 5 years old. The complete package is easy to see and ready for your immediate enjoyment.

31 Footbridge Trl, Ocean Pines

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$624,990
3 Beds ⋅ 3 Baths
This brand new construction by Gemcraft Homes offers a rear screened porch, and is located on an extra-large cul-de-sac lot overlooking the Ocean Pines Golf Course! The Nottingham is a modern ranch-style home with 3 bedrooms, 2 baths, and a 2 car garage. The expansive Great Room area with 9' ceilings and gas fireplace opens to the Kitchen, that is ready for entertaining and cooking comforting meals for family and friends. An open dinette and large kitchen island offer an abundance of space for informal dining. The private Owner’s Suite includes an ensuite bath featuring a double vanity, water closet, and walk-in closet. For upgraded luxury, the Venetian Owner's Bath includes a Ceramic Tile Base shower with Glass Door, Granite Vanity Top, Rectangular Sink Bowls, and a Tall Vanity with Drawer Base. Two additional bedrooms with a hall bath and laundry room complete the floor plan. The award winning community of Ocean Pines is located just a short drive away from Ocean City's beaches and boardwalk, Assateague Island National Seashore, the historic downtown Berlin! A Gemcraft Smart Home Bundle is included, plus ask about our Builder Incentives! Photos shown are of a similar home. Estimated completion date November 2026.

277 Windjammer Rd, Ocean Pines

Listing courtesy of Hileman Real Estate-Berlin. Contact: (410) 208-9200
$330,000
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 on a quiet cul de sac, 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
$439,000
3 Beds ⋅ 3 Baths
Located in the Ocean Pines community, this 3-bedroom 2 1/2-bathroom home has so much to offer including a 2-car attached garage! When you enter the home, you will be immediately impressed by the sunny living room featuring vaulted ceilings and skylights! The owner recently upgraded the flooring with luxury vinyl plank which runs through the main level common areas. The kitchen features white cabinetry and stainless-steel appliances. The sunroom also has vaulted ceilings and a gas fireplace with mantel. The sunroom leads to a large deck that is freshly painted. The deck has peaceful views of trees and privacy. The first-floor primary bedroom as features views of the back yard and a walk-in closet. What you will notice most about this home is that it is flooded with natural light. Almost every room features large windows. On the second level of the home there are two bedrooms and a bathroom. There is also a walk-in attic storage room that could be used to conveniently store holiday decorations. This home was built by T&G Builders and is the Skipjack II model. The hot water heater was replaced in 2023 and the roof was replaced in 2026. Builder marketing floorplan shows square footage of 1659, while tax record shows 1494. Make an appointment to see this well maintained home today!

369 Ocean Pkwy, Ocean Pines

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400
$1,399,000
5 Beds ⋅ 5 Baths
Rare Captain's Hill opportunity — a custom 5-bedroom, 4.5-bath waterfront home on a 0.47-acre corner lot with a private boat slip, lift, and inground pool. Homes in this neighborhood trade hands once in a generation. Set on nearly half an acre at the corner of Shoal Drive and Golf Course Road, this 2,994-square-foot custom home was built in 1997 and has been meticulously maintained. Deeded waterfront rights include exclusive use of the pier on the northerly half of the shared bulkhead, with a boat lift already installed and ready for the season. The canal opens directly to the back bays and the Atlantic beyond. Inside, hardwood floors run throughout. The upper level of the main house holds a spacious primary suite plus two additional bedrooms, sharing a full bath. The main floor offers a gourmet kitchen with upgraded countertops, stainless appliances, and a gas range. A gas fireplace anchors the living room, and there's also a bedroom and hall bath for overflow guests. A screened three-season gazebo captures cross-breezes and canal views. A private staircase off the kitchen leads to what may be the home's most flexible space: a large bonus suite above the garage with its own full bath and mini-fridge. Big enough to function as three zones at once - a home office, a workout area, and a full lounge with room for a sectional and oversized TV. It lives like a private apartment, ideal for a work-from-home setup, in-law arrangement, teen retreat, or long-stay guest quarters. Outside, the inground pool is framed by a paver patio and a covered gazebo with grill/skillet, table, and a bar area. The backyard is fully fenced, and professionally landscaped with mature plantings. An oversized two-car garage with tall ceilings and extended depth accommodates full-size trucks, trailers, and workshop use. Captain's Hill is one of Ocean City's most established communities and carries no HOA fees. It's a genuine rarity for a waterfront enclave this close to town. Furnishings and recreational equipment available separately. Schedule a private tour today. This one will not sit.

12944 Shoal Dr, Ocean City

Listing courtesy of Coldwell Banker/Bud Church Rea. Contact: (410) 524-7888
$814,900
4 Beds ⋅ 4 Baths
Stunning New Construction in Ocean Pines – Move-In Ready! Built by RBR Homes LLC, this exceptional 4-bedroom, 3.5-bathroom home has just been completed and is ready for immediate occupancy in the desirable Triple Crown section of Ocean Pines. From the moment you arrive, you'll appreciate the home's charming coastal character, highlighted by beautiful blue siding and an inviting front porch. Inside, thoughtful design, high-end finishes, and exceptional craftsmanship are evident throughout. The first floor features a spacious family room with a cozy gas fireplace, creating the perfect gathering space year-round. The family room flows seamlessly into the gourmet kitchen, a true chef's dream, featuring premium Café appliances, quartz countertops, white custom cabinets,  a large center island with seating, and a custom tile backsplash. Just off the kitchen, you'll find a butler's pantry, wine cooler, and additional pantry storage for added convenience. The dining area is filled with abundant natural light, creating a bright and welcoming space for everyday meals and entertaining. The luxurious first-floor primary suite offers a private retreat, complete with a spa-inspired bath featuring a designer-tiled walk-in shower, freestanding soaking tub, and a custom walk-in closet with built-in organization. Additional first-floor highlights include a dedicated home office, laundry room, luxury vinyl plank flooring, and custom lighting throughout the home. Upstairs, you'll find a spacious second family room, three additional bedrooms, and two full bathrooms, providing plenty of room for family and guests. Step outside to enjoy the covered rear patio overlooking a freshly sodded yard. Fencing is permitted with HOA approval, making the outdoor space ideal for children and pets. Enjoy everything the amenities rich community of Ocean Pines has to offer, including: 5 swimming pools (1 pool is enclosed and heated and open year-round), Yacht Club and restaurant, marina, boat ramp, golf course with club house, Community Center, multiple playgrounds and parks, tennis basketball and pickleball courts, skateboard park, walking/biking trails, community police and fire departments and beach club on the ocean with ocean front pool and parking, and more! Come take a look today before it's SOLD!!Don't miss this opportunity to own a beautifully crafted new home in one of the area's most sought-after communities.

75 King Richard Rd, Berlin

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211