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$550,000
3 Beds 2 Baths
Nestled on approximately 2.5 peaceful acres, this charming property offers the perfect blend of privacy, tranquility, and convenience. Ideally located just minutes from downtown Berlin, shopping, dining, and the area’s beautiful beaches, you’ll enjoy the best of country living with easy access to everything the Eastern Shore has to offer. Lovingly maintained over the years, this unique home is filled with warmth and character. The spacious four-season sunroom is the perfect place to relax and enjoy the beauty of every season, while the detached garage provides additional storage, workspace, or parking. Start your mornings with a cup of coffee on the inviting front porch as you take in the peaceful surroundings and quiet setting. If you’re looking for space, privacy, and a home that has been cared for with love, this is a must-see property. Don’t miss this incredible opportunity to own a beautiful home on 2.5 acres in a highly desirable location just outside of Berlin. Schedule your private showing today!

10376 Georgetown Rd, Berlin

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400

$315,000
3 Beds 2 Baths
Escape to the peace and beauty of the Eastern Shore with this charming 3-bedroom, 2-bath ranch nestled in a serene country setting. Surrounded by wide-open green space and mature trees, this inviting home offers the perfect blend of comfort, privacy, and everyday convenience. Step inside to discover a warm and welcoming floor plan featuring a bright living area, a spacious dining room ideal for gathering with family and friends, and a well-appointed kitchen with abundant cabinetry, generous counter space, and a functional breakfast bar. The split-bedroom layout provides privacy, while the spacious primary suite includes a full bath for your own private retreat. Outside, you'll find endless room to relax, garden, entertain, or simply enjoy the peaceful surroundings. Whether you're sipping your morning coffee on the front porch, watching the sunset over the expansive yard, or appreciating the quiet of country living, this property offers a lifestyle that's hard to find.

6720 Porters Crossing Rd, Snow Hill

Listing courtesy of ERA Martin Associates. Contact: 4107491818

$625,000
4 Beds 4 Baths
Coastal living at its finest! Welcome to this exceptional three story home nestled in one of the area’s most desirable water oriented communities, just 5 miles from Ocean City, MD, and Assateague Island National Seashore Offering spacious bedrooms, 4 full bathrooms, and flexible living spaces throughout this home perfectly blends comfort, functionality, and coastal charm. The inviting open concept main level is ideal for entertaining, featuring generous living and dining areas that flow seamlessly together. Upstairs, the expansive primary suite provides a private retreat with ample space to unwind, read, or enjoy your morning coffee. Two additional bedrooms and another full bath complete the second floor. The third level offers incredible versatility and can easily serve as a fifth bedroom, guest suite, home office, media room, fitness space, or playroom tailoring to your lifestyle needs. Outside your door, enjoy resort style amenities including multiple pools, a fitness center, clubhouse, and crabbing pier , all while the HOA takes care of your lawn maintenance, giving you more time to enjoy the coastal lifestyle. Whether you’re searching for a year round residence, vacation getaway, this home offers the perfect combination of space, location, and lifestyle. Don’t miss your chance to own a piece of Maryland’s beautiful Eastern Shore.

12209 Ocean Vista Dr, Berlin

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400

$550,000
3 Beds 3 Baths
Your dream home is waiting for you here on 2 acres! Custom built in 2006 to replace an older primary home, this quality home has 3 bedrooms- the primary is on the first floor along with a luxurious primary bath and walk-in-closet. Guest 1/2 bath. 2 additional bedrooms and bath are on the second floor. Formal Living room and dining room greeting you along the foyer entrance. Spacious Family room with pellet stove and gas fireplace add living space for all. Kitchen has a bar area for seating plus a spacious casual breakfast room and all stainless-steel appliances. Large 10x10 rear deck with awning for outdoor enjoyment. Circular paved driveway for easy access to you 2-car built in garage. 3 plus detached garages and 2 sheds make a place for all your lawn equipment and fun toys. Easy to see in the quaint village of Bishopville.

13308 Hatchery Rd, Bishopville

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

$975,000
5 Beds 4 Baths
Coastal elegance meets modern comfort in this beautifully appointed, fully furnished home built in 2023, located in the highly sought-after Bayside community. Thoughtfully designed with a light and airy coastal vibe, every detail has been carefully selected, making this stunning home truly move-in ready. Offering 5 spacious bedrooms, 4 full bathrooms, and a dedicated home office, this home provides the perfect blend of luxury, comfort, and functionality. Upon entering, you’ll find a private home office just off the foyer, creating the ideal space for working remotely, studying, or enjoying a quiet retreat. The open concept floor plan is designed for effortless entertaining, with the spacious living room flowing seamlessly into the chef-inspired kitchen featuring quartz countertops, stainless steel appliances, a gas range, an oversized island, abundant cabinetry, and a generous dining area just off the kitchen that remains connected to the heart of the home perfect for everyday meals, holiday gatherings, and entertaining family and friends. The first-floor primary suite is a peaceful retreat featuring an elegant tray ceiling, a spacious walk-in closet, an additional closet providing extra storage or the convenience of a his-and-hers setup, and a beautifully appointed en suite bathroom. A second bedroom and full bathroom are also conveniently located on the main level, providing flexibility for guests or multigenerational living. Upstairs, you’ll find three additional bedrooms, two full bathrooms, and a spacious loft currently set up as a game room, offering endless possibilities as a second family room, media room, playroom, or recreation space. Additional highlights include a tankless water heater for energy efficiency and endless hot water, a blacktop driveway, and tasteful coastal finishes throughout. Enjoy your morning coffee on the inviting front porch or unwind on the covered rear porch the perfect place for outdoor dining, entertaining, or simply relaxing after a long day. Located within walking distance of Bayside’s exceptional amenities, residents enjoy a clubhouse, fitness center, indoor and outdoor pools, basketball and tennis courts, scenic ponds, a kayak launch with storage lockers, and a crabbing pier. Perfectly situated between Assateague Island and the beaches and Boardwalk of Ocean City, this exceptional home offers the ideal combination of resort-style amenities, coastal charm, and everyday convenience. Whether you’re searching for a year-round residence, a vacation getaway, or an investment opportunity, this turnkey Bayside home is one you won’t want to miss!

12420 Coastal Marsh Dr, Berlin

Listing courtesy of Sheppard Realty Inc. Contact: (410) 723-7070

$269,000
3 Beds 2 Baths
Professional Pictures coming soon. If you've been searching for peaceful country living without sacrificing convenience, welcome to Sheephouse Road. Tucked back from the road and surrounded by woods, and scenic farmland, this charming ranch home offers the privacy and tranquility you've been looking for while remaining just a short drive from town. Relax on the welcoming front porch as you take in picturesque views of the surrounding fields, or step inside to discover the ease of one-level living with a bright, open-concept floor plan that's perfect for everyday life and entertaining. Just off the main living area, a spacious three-season room provides additional living space and peaceful views of the woods beyond, making it an ideal spot for morning coffee or evening relaxation. Outside, you'll find plenty of room to enjoy the outdoors. The fenced backyard offers a safe place for pets to play, while the heated above-ground saltwater pool lets you cool off and extend your swimming season well into the spring and fall. The property also includes a detached one-car garage, two storage sheds, and a covered boat/carport, providing ample space for vehicles, hobbies, and outdoor equipment. Situated on more than 1½ acres, there's plenty of room to roam, garden, or simply enjoy your own private slice of the countryside. If you've been dreaming of a quiet rural setting with comfortable living and room to breathe, don't miss your opportunity to make this Sheephouse Road property your own before someone else does.

3520 Sheephouse Rd, Pocomoke City

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400

$549,900
3 Beds 2 Baths
Rare opportunity to own an expansive home on 1.24 premium acres in historic Berlin Proper! This unique property backs directly to Stephen Decatur Park and features a spacious 4BR/2.5BA main house with a large country kitchen and an attached 1-car garage. A private, separate-entrance 2BR/1BA garage apartment provides immediate guest quarters. The park-like grounds boast a pool, multiple detached garages, and ample storage for mowers, bikes, and beach toys. Located on a highly desirable street just minutes from Assateague Island's beaches and Ocean City's famous boardwalk. For ultimate privacy or development, 19 Burley is also listed for sale—buy both properties together to create your own massive estate!

17 Burley St, Berlin

Listing courtesy of Sheppard Realty Inc. Contact: 4437830299

$169,900
3 Beds 1 Baths
Discover this renovated ranch-style home in Pocomoke City. With 820 sq. ft. of well-designed living space, this 3-bedroom, 1-bathroom residence is perfect for those seeking comfort and style. Step inside to find a warm and welcoming interior adorned with crown moldings, chair railings and laminated plank flooring that add a touch of elegance. The updated country-style kitchen features granite countertops, wood cabinetry and stainless-steel appliances, making it a delightful space for culinary adventures. The cozy dining area is perfect for gatherings, while the entry-level bedrooms offer convenience and flexibility. Outside, the property features a cleared lot of 0.19 acres, complete with a front and rear yard, ideal for outdoor activities or serene relaxation. Enjoy the benefits of streetlights and sidewalks in this peaceful neighborhood, enhancing your daily strolls or evening walks. The proximity to the stunning Chesapeake Bay adds a unique allure, providing opportunities for water activities and breathtaking views. With new upgrades, this home combines modern amenities with timeless appeal. Don't miss the chance to make this property your own!

506 Laurel St, Pocomoke City

Listing courtesy of Century 21 Downtown. Contact:

$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

$1,300,000
4 Beds 3 Baths
Unlock exceptional income potential in the heart of downtown Ocean City with this versatile 4-bedroom, 3-bath single-family home at 106 Philadelphia Avenue. Built in 1930 and offering approximately 2,080 square feet of living space on a 3,275-square-foot lot, this property sits just two blocks from the beach and two blocks from the bay—placing you steps from the Boardwalk, restaurants, shops, nightlife, and the best of coastal living. What sets this property apart is its flexible multi-level layout designed for maximum rental returns or hybrid owner-occupant use. Each floor features its own bedrooms, full baths, and kitchen, along with independent front and rear entries. Live in one level while renting the other, or operate the entire home as a high-demand short-term vacation rental or steady year-round investment. The attic provides additional conversion potential for even more living or rental space. With parking for up to four vehicles, ceiling fans, and essential appliances including washer, dryer, range/oven, and microwave, the home is ready for immediate use. Whether you’re seeking a primary residence that generates supplemental income, a pure investment property, or a combination of both, 106 Philadelphia Avenue delivers strong income-producing potential in one of Ocean City’s most desirable downtown locations.Don’t miss this rare opportunity to own a flexible, cash-flow-friendly property in the heart of Ocean City.

106 Philadelphia Ave, Ocean City

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

$375,000
3 Beds 2 Baths
OPEN HOUSE: Sunday, August 9th 11:30-1:30. 7150 Arcadia Circle in Arcadia Village, just 7 Mi. south of Berlin, Maryland! This charming rancher features one-floor living with soaring ceilings, open floor plan, plenty of windows creating a bright and airy living space. Open kitchen with white cabinets, center island and large pantry. Back deck for morning coffee time! Charming front porch to welcome guests! Large primary suite with ensuite bath and "his" and "her" closets. BONUS: Attached garage and the home backs to undisturbed forestry. Arcadia village is a small neighborhood of only 41 homes. LOW HOA of less than $500 per year. Just beyond the neighborhood is Newark Park (a trail from the neighborhood will take you there!) Newark, Maryland is nestled between Berlin and Snow Hill (just a short 10 minute drive to either). And just a short drive to all things Worcester County, Maryland has to offer; quaint historical towns, Assateague Island, Ocean City beaches, boardwalk and MORE!!

7150 Arcadia Cir, Newark

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400

$299,900
2 Beds 2 Baths
Nestled in the serene enclave of Nassawango Hills this 2bedroom 2 bath log cabin is a home that embodies the essence of luxury living while offering the warmth and comfort of a true retreat. This exquisite residence, set on a generous 0.55-acre lot, invites you to experience a lifestyle defined by tranquility and elegance. As you step inside, you are greeted by the rich textures and natural beauty of the log construction, which creates an inviting atmosphere throughout. The spacious 1,370 square feet of thoughtfully designed living space features two well-appointed bedrooms and two full bathrooms, ensuring ample room for relaxation and rejuvenation. The heart of the home is a cozy living area, complete with a charming fireplace that serves as a focal point for gatherings, providing warmth and ambiance during cooler evenings. The open layout seamlessly connects the living space to the kitchen, where culinary enthusiasts will appreciate the potential for creating gourmet meals. Large windows allow natural light to flood the interior, enhancing the home's warm and welcoming vibe. Step outside to discover the expansive outdoor space, perfect for enjoying the beauty of nature. The property includes a shed for additional storage, ensuring that your outdoor activities can be enjoyed without clutter. The surrounding landscape offers a peaceful retreat, ideal for morning coffee or evening stargazing. Parking is a breeze with a convenient driveway, providing easy access to your home. While the property does not feature a pool, the lush surroundings and spacious yard offer endless possibilities for outdoor enjoyment, from gardening to hosting summer barbecues. This is more than just a home; it's a lifestyle choice that embraces the beauty of nature and the comforts of modern living. Whether you seek a weekend getaway or a permanent residence, this log home offers a unique opportunity to immerse yourself in a community that values peace, privacy, and the joys of life. Experience the charm and elegance of this exceptional property, where every detail has been crafted to create a sanctuary that feels like home. Don't miss your chance to make this enchanting log home your own. The current owners tied all baseboards to 1 thermostat, new shed, new toilets, painted, added new light fixtures, plumbing work & leaving 4 portable a/c units.Furniture negotiable. Blueprints available upon mortgage approval for original 3 bedroom layout plans if interested in converting to a 3 bedroom home.

3842 Algonquin Trl, Snow Hill

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 3023515000

$525,000
3 Beds 2 Baths
Discover the best of coastal living in this beautifully maintained 3-bedroom, 2-bath waterfront corner condominium in the heart of Ocean City. Complete with a private boat slip and an unbeatable location just off 26th Street, this exceptional property is a dream for boating enthusiasts and beach lovers alike. Step inside to find a spacious, thoughtfully updated interior featuring a beautifully appointed kitchen with solid maple hardwood cabinetry, a convenient wet bar, and tastefully renovated bathrooms (approximately $20K in bathroom improvements), showstopping terracotta tiled flooring throughout, expansive windows with plantation shutters, and electrical & lighting upgrades throughout.. The generous primary suite offers a large walk-in closet, providing ample storage and everyday convenience. Enjoy peace of mind with major updates already completed, including a new HVAC system installed in 2020, a new water heater in 2022, and the $90,000 building assessment already paid by the seller for the comprehensive building envelope rebuild. With full southern exposure, this light filled home is warm and bright. Relax on your expansive private balcony overlooking the bay and enjoy spectacular sunsets and unparalleled waterfront views. Ideally located just a short walk or bike ride to the beach, this home is also moments from Ocean City's favorite restaurants, lively bars, mini golf, shopping, Jolly Roger’s Amusement Park, and entertainment. With strong rental income potential, this property is an outstanding opportunity as a primary residence, vacation getaway, or investment. Offering the perfect blend of waterfront living, modern updates, and an unbeatable location, this is coastal living at its finest.

413 Bayshore Dr Unit #201, Ocean City

Listing courtesy of Coastal Life Realty Group LLC. Contact: (443) 235-8382

$369,900
3 Beds 3 Baths
Welcome to 3 Winter Quarters Drive, a beautifully crafted new construction home offering timeless Colonial style with modern finishes in a private, in-town setting. The open floor plan features wide-plank LVP flooring, a bright living space, and a stunning kitchen with off-white shaker cabinets, stainless-steel appliances, marble-look quartz countertops, and a large center island. Upstairs offers three bedrooms, including a spacious primary suite with a private bath and walk-in closet. Enjoy the welcoming front porch, low-maintenance composite rear deck, and generous yard with landscaping to be completed soon. Conveniently located near Cypress Park, the Pocomoke River, shopping, dining, and an easy drive to Wallops Island, Virginia's Eastern Shore, and Ocean City. Enjoy the perfect blend of style, comfort, and small-town living. Schedule your private showing today!

3 Winter Quarters Dr, Pocomoke City

Listing courtesy of Whitehead Real Estate Exec.. Contact: 4107494663

$1,699,000
5 Beds 5 Baths
Welcome to one of Sunset Island's most desirable waterfront addresses. Perfectly positioned to capture breathtaking south-facing views of the bay, this beautifully appointed 5-bedroom, 4½-bath coastal retreat offers the ideal blend of luxury, comfort, and resort-style living. A versatile first-floor den is currently configured as a sixth bedroom, providing exceptional flexibility for guests, a home office, media room, or additional living space. From the moment you arrive, you'll appreciate the home's prime location—just a short stroll to Sunset Island's award-winning clubhouse, indoor and outdoor pools, private bay beaches, restaurant, general store, and all of the community's exceptional year-round amenities. Multiple waterfront balconies and expansive outdoor living spaces invite you to relax with your morning coffee, soak in spectacular sunsets, or entertain while overlooking the sparkling bay, beach, and pool. Inside, spacious living areas are thoughtfully designed for gathering family and friends, while the oversized garage offers plenty of room for vehicles, beach gear, and bikes. Best of all, Ocean City's pristine Atlantic beaches, dining, shopping, and entertainment are just a short walk away. Whether you're searching for an exceptional vacation home, a high-demand investment property, or a full-time coastal residence, this waterfront gem delivers the lifestyle you've been dreaming of. Once you experience the views, the location, and the unmatched amenities of Sunset Island, you'll understand why so many people never want to leave.

5 Beach Side Mews, Ocean City

Listing courtesy of RE/MAX Advantage Realty. Contact: (410) 723-3600

$669,000
3 Beds 3 Baths
1222 Carrollton Lane is a beautifully crafted 2021 coastal home offering the perfect blend of modern comfort and an unbeatable walk-to-marina lifestyle. Nestled in the sought-after Colonial Village section of Ocean Pines, this move-in ready 3-bedroom, 2.5-bath home features approx. 2,256 SF of thoughtfully designed first-floor owner's suite with a custom closet system. The open-concept floor plan is ideal for both everyday living and entertaining. Enjoy abundant southern light. Get creative with a conditioned bonus room. The possibilities are endless; TV room, office, or extra storage. Step outside to enjoy professional privacy landscaping in a rare expansive backyard. Enjoy a walk to one or both marinas, waterfront dining, walking trails, live music, or golf just minutes away. Historic downtown Berlin, shopping, OCMD or Assateague National Seashore is a short drive. This move-in ready home offers the luxury, coastal lifestyle you're looking for.

1222 Carrollton Ln, Berlin

Listing courtesy of Sell Your Home Services. Contact: 8882193009

$9,500,000
6 Beds 5 Baths
This 37-acre Waterfront Estate in the desirable West Ocean City Community of Captains Hill stands among Worcester County’s true legacy properties. A rare combination of Coastal Luxury, privacy, acreage and future opportunity. Set on a expansive rise overlooking the bay, the Estate commands sweeping water and skyline views that shift elegantly from sunrise to the golden glow of sunset. A long driveway leads you to the 8000+ Sq Ft Coastal Residence, a grand yet serene retreat surrounded by park-like grounds and mature landscape that creates an atmosphere of total privacy. The main Estate and grounds encompass 27 acres that feature a diverse landscape designed for both beauty and functionality. Such highlights include a 3-acre freshwater pond that anchors the properties tranquil setting, an outdoor pool with surrounding deck ideal for families and entertaining, an expansive lawn for gatherings and pets, a large covered porch perfect for enjoying the broad water views and nature, covered parking entrance and a three-car garage. The residence itself offers the architectural presence and scale expected of a Coastal Estate of this magnitude, with generous living spaces, impressive ceiling heights and endless potential for customization or enhancement. In addition, this Estate offers additional parcels and development potential that allows for flexibility for future use. Included in the offering is a 2.73-acre Waterfront Lot and 20 plated lots with their own road frontage. This rare land portfolio provides exceptional opportunities, ideal for a private compound, multi-generational retreat, curated development or long-term investment that makes this property uniquely valuable. Opportunities of this size, location and versatility rarely ever come to market. With commanding views, coastal proximity, and expansive acreage, this Captain’s Hill Estate stands as one of the region’s premier offerings, a property with both present-day grandeur and limitless future potential. A Coastal Treasure without equal.

12903 Windy Dr, Ocean City

Listing courtesy of Holiday Real Estate. Contact: 4105247700

$469,900
3 Beds 3 Baths
Imagine coming home to your own secluded haven surrounded by nature. This impeccably maintained 3-bedroom, 3-bath home delivers effortless one-level living designed around quality, comfort, and coastal entertainment. Step inside to an airy, open layout bathed in natural light, highlighted by updated LVP flooring throughout and a cozy fireplace serving as the warm focal point of the living space. The gourmet kitchen is a true chef’s delight, featuring an expansive island and stunning quartz countertops—making it an absolute dream for hosting and daily prep. Outdoor living is at its finest; relax on the awning-covered front deck or retreat to the generous screened porch to take in the serene, wooded views. Located in an amenity-rich Ocean Pines community, you'll love having pools, golf, and marinas right at your fingertips —all just a short drive from the beaches and excitement of Ocean City!

39 King Richard Rd, Ocean Pines

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

$759,000
4 Beds 4 Baths
As you enter this elegant home from a huge covered front porch you will be amazed at the grandeur of this open concept floor plan with a massive entrance foyer. Step into a great room featuring high ceilings, recessed lighting, lots of windows, gleaming hardwood floors and a natural gas fireplace. The bright and spacious kitchen features tiered center island granite counters. The dining room has french doors opening to lovely back deck. This home features not one but two master/primary bedrooms with ensuite baths. One is on the first floor and one is on the second floor. There is a study with bay windows off the entrance foyer, a sunporch off the first floor master/primary bedroom, a half bath, large laundry room off kitchen and ample closets throughout. Upstairs you will find a family room, master/primary bedroom with ensuite bath, 3rd and 4th bedrooms, walk-in closets and 3rd full bath. From the back deck you can enjoy the privacy of a wooded back yard and the golf course beyond. The owners chose upgraded electrical package including extra electrical wall switches, 17 extra electrical receptacles, ceiling heat lamps in both master baths, exterior rear flood lights, 9 dimmer switches and 5 additional GFI exterior receptacles. Discover all of this unparalleled allure of life in Glen Riddle Golf Club Community complete with 96 slip marina, lit tennis and pickleball courts, huge club house with state of the art fitness center, sauna and locker rooms, game room, meeting room, on site professional property management, large outdoor pool with integrated spa and kids splash pad and of course two 18 hole golf courses with driving range available for membership. The gated community of Glen Riddle is located just minutes from the beautiful Ocean City Beaches, Assateague Island National Park and the town voted America's Coolest Smalltown, Berlin Md. where the famous movie Runaway Bride was filmed starring Richard Gere and Julia Roberts. Come visit this beautiful, perfectfully maintained, original owner home in the amazing community of Glen Riddle and start living the lifestyle you have dreamed of enjoying

11654 Maid At Arms Ln, Berlin

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

$1,035,000
4 Beds 3 Baths
Discover exceptional waterfront living in Bayview Estates. Perfectly positioned on a picturesque creek with a private dock and easy access to the bay, this meticulously maintained home offers timeless coastal elegance and an effortless indoor-outdoor lifestyle. The thoughtfully designed floor plan features three bedrooms in the main residence, including a main-level primary suite with a walk-in closet and spa-like bath. A vaulted great room with a wet bar, spacious family room, screened porch, and expansive waterfront decks create the perfect setting for entertaining or relaxing while taking in the breathtaking water views. A detached two-car garage with a finished bonus room provides an ideal fourth bedroom, guest retreat, or private office. An outdoor shower, generous driveway, and beautifully maintained grounds complete this exceptional property. Bayview Estates offers a clubhouse, pool, tennis courts, and a private boat ramp—all with a low $375 annual HOA fee. Experience the finest in coastal waterfront living at 12101 Salt Point Road.

12101 Salt Point Rd, Bishopville

Listing courtesy of Monument Sotheby's International Realty. Contact: 4437087074

$899,000
3 Beds 3 Baths
There's golf course frontage and then there's this. Set on a prime corner lot overlooking the 11th green of GlenRiddle's War Admiral Course, this home gives you a front-row seat to one of the community's signature holes. Whether you're sipping your morning coffee in the sunroom or winding down on the porch in the evening, you'll spend your day watching approach shots, birdie putts, and one of the best views GlenRiddle has to offer. Inside, the home is just as impressive. With 3,378 square feet, 3 bedrooms, 2.5 baths, and a first-floor primary suite, the layout is as practical as it is inviting. Best of all, it's being offered completely furnished, making this a true turnkey opportunity. The home has been meticulously maintained and feels virtually brand new. The current owners didn't just maintain it, they upgraded it. The first floor features a dual-fuel heat pump and gas furnace, the sunroom has its own mini-split system, there's a tankless gas water heater, premium window blinds throughout, and yes... three dishwashers, because entertaining should be easy. A brand-new epoxy garage floor was installed August 4. Life in GlenRiddle extends far beyond your front door. Residents enjoy two championship golf courses, an outdoor pool, fitness center, pickleball and tennis courts, a billiard room, marina, Ruth's Chris Steak House, and optional golf memberships, all within one of the area's most sought-after gated communities. Homes with this view don't come along often. Homes that come fully furnished, show like new, and let you move right in are even harder to find.

10001 Flotilla Ln, Berlin

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

$299,000
3 Beds 3 Baths
Welcome to Southern Fields! Built in 2023 and impeccably maintained, this like-new 3-bedroom, 2.5-bath home offers modern style, quality construction, and versatile living space. The finished garage is equipped with a mini-split heating and cooling system, making it ideal for a home office, recreation room, fitness area, playroom, or additional living space. Step outside to a fully fenced backyard featuring low-maintenance composite decking, perfect for entertaining, relaxing, or enjoying time with family and pets. A storage shed provides additional space for lawn equipment, tools, and outdoor gear. Conveniently located in the desirable Southern Fields community, this home is just minutes from schools, shopping, restaurants, and downtown Pocomoke City. Enjoy easy access to Ocean City, Assateague Island, Chincoteague Island, and the NASA Wallops Flight Facility, making this an excellent location for commuters, beach lovers, and anyone looking to enjoy the best of Maryland's Eastern Shore. Move-in ready and waiting for its next owner!

1922 N Old Mill Dr, Pocomoke City

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 7575642600

$899,900
3 Beds 2 Baths
Experience the best of coastal waterfront living in this charming 3-bedroom, 2-bath home situated on a spacious 7,500-square-foot lot in the desirable Caine Keys community. Just a short stroll to the beach, this exceptional property offers the perfect combination of waterfront living, outdoor recreation, and coastal convenience. Lovingly maintained and never rented, this home has been cherished as a private family retreat and is ready for its next owners to create lasting memories. Inside, you'll find a warm and inviting floor plan designed for comfortable everyday living and entertaining. The lovely kitchen features a convenient breakfast bar and flows seamlessly into the dining area, creating the perfect gathering space for family meals and entertaining friends. The spacious living area is filled with natural light and offers a relaxing atmosphere after a day on the water or at the beach. The primary bedroom is a peaceful retreat complete with a private en suite bath. A generously sized second bedroom provides comfortable accommodations for family and guests, while the hall bath and separate laundry room add convenience. The waterside sunroom/third bedroom, currently being used as a Florida room, overlooks the water and offers breathtaking views, making it the perfect place to enjoy your morning coffee, read a book, or simply relax while watching the boats go by. Step outside to discover your own waterfront oasis. The beautifully designed paver courtyard is ideal for grilling, entertaining, or enjoying warm summer evenings. The expansive deck overlooking the canal is the perfect place to unwind with your morning coffee or evening cocktail while taking in the refreshing ocean and bay breezes. There is a nice awning as well for the hot summer days. Whether you enjoy boating, paddleboarding, kayaking, fishing, or simply watching the sunset over the water, this location offers endless opportunities for waterfront recreation right from your backyard. The attached garage and storage shed provide plenty of room for all of your beach gear, bikes, kayaks, and fishing equipment. Located just moments from Ocean City's beautiful beaches, restaurants, shopping, and entertainment, 131 Old Wharf Road offers the ideal blend of tranquility and convenience. Whether you're searching for a primary residence, a vacation getaway, or an investment opportunity, this rare waterfront gem is ready for you to start enjoying the coastal lifestyle you've always dreamed of.

131 Old Wharf Rd, Ocean City

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

$389,000
3 Beds 2 Baths
This beautifully updated 3-bedroom, 2-bath home is tucked away on a quiet cul-de-sac and sits on an oversized lot with a 2-car garage. Enjoy outdoor living at its best with a screened porch, spacious deck, and a fully fenced backyard that's perfect for kids and pets to play safely. Inside, you'll find new luxury vinyl plank flooring throughout, fresh paint, updated light fixtures, and solid surface countertops in both the kitchen and primary bath. The hall bath features a new vanity, while the kitchen is equipped with a brand-new range. The hot water heater is approximately two years old, providing added peace of mind. Storage is plentiful with a coat closet, linen closet, and attic with pull-down stairs. Located in the highly desirable Ocean Pines community, residents enjoy an exceptional lifestyle with amenities that include golf, marinas, parks, swimming pools, pickleball and tennis courts, a yacht club, beach club, farmers market, and miles of scenic walking trails—all just minutes from the beaches, boardwalk, dining, and entertainment of Ocean City.

10 Stonemeadow Ct, Ocean Pines

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

$499,900
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

$390,000
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