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$799,000
3 Beds 4 Baths
An extraordinary opportunity awaits with this remarkable canal-front home offering direct water access to Assawoman Bay via Greys Creek—your personal gateway to Ocean City by boat. With no HOA fees, oversized garage storage for boats or RVs, and a newer private dock with water, electric, and a separate SlideMoor docking system, this home is a true gem for boaters and waterfront enthusiasts. Built in 2008 and impeccably maintained, this 3-bedroom home with 2 large bonus rooms (one over garage and another additional bonus room upstairs- plus a loft), boasts over 3600 sq ft of stylish, open-concept living space. There is updated flooring throughout the main level and carpeting upstairs. Fresh paint throughout—a true blank canvas to personalize. The kitchen features recently replaced countertops, updated appliances, plus a walk-in pantry. There are two cooking areas, a gas cooktop and a separate range/oven. The first-floor primary suite has a remodeled en suite bath and a spacious walk-in closet. The two-story family room has a newer pellet stove and overlook from the 2nd-floor loft. Multiple flex spaces: den/office, formal dining, bonus room, and second living areas upstairs and down. Enjoy seamless indoor/outdoor living with a screened porch, freshly re-screened, leading to a low-maintenance composite deck with two propane hookups—ideal for a grill and outdoor fireplace. The attached garage features 3 automatic doors (2 front, 1 rear), 12' ceilings (room for RV, boat, or car lift), back-up heating system to support the home’s energy-efficient geothermal water furnace system. There is a newer well pump and an encapsulated crawlspace with dehumidifier. Located on a county-maintained road, no city taxes, and easy access to both Ocean City & DE Beaches. This property is ideal as a full-time residence or vacation escape. Whether you're relaxing indoors, entertaining outdoors, or setting off by boat to the beach, this home offers effortless Eastern Shore living at its finest. Don’t miss this rare waterfront value—schedule your private showing today!

12212 Brant Rd, Bishopville

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

$425,000
4 Beds 2 Baths
Don't miss out on this incredible opportunity to own a piece of Ocean Pines paradise. With its unbeatable location, stunning design, and endless possibilities, this remodeled 4 bedroom, 2 bath home is the perfect haven for anyone looking to experience the best of coastal living. Brand new 2.5 ton Rheem heat pump system and Honeywell thermostat just installed June 2026. This home in 2022 went under major rehab with new architectural roof, new siding and shutters, high efficiency tilt in windows, new flooring throughout, vanities and a beautiful gourmet kitchen with a large granite breakfast bar that seats 6. One of the larger lots in the Pines with the home situated to easily add a two-car garage. South gate living at its best and just a few houses over from the bay. Schedule a showing today and make your dreams a reality!

120 Robin Hood, Ocean Pines

Listing courtesy of Sheppard Realty Inc. Contact: 4437830299

$1,650,000
4 Beds 3 Baths
Presenting this finest and elegant, custom-built waterfront home, situated in the finest neighborhood in OC. This is truly an entertainer's paradise. You will find an open floor plan, that is wrapped in windows, offering majestic views. There are 4 BR and 3 BA, and a 35 Ft pier. First floor there are 2 guest rooms and can easily sleep 8 Guests. The main level is host to a large living room with Panoramic views. Gourmet Kitchen with all SS Appliances. This is a wonderful once in a life time opportunity to own the best of ocean city, Maryland. Come home to coastal living at its finest. Qualified Buyers Only, no Solicitation ! This is a LIMITED SERVICE LISTING: Do NOT contact the listing agent. Contact the OWNER/SELLER directly.

505 S Surf Rd, Ocean City

Listing courtesy of TTR Sotheby's International Realty. Contact: (703) 745-1212

$699,900
4 Beds 4 Baths
Fresh Look. Fresh Price. Fresh Opportunity. **Now Offered at $699,900 — Recently Reduced by $25,000!** Sometimes the perfect home simply needs the right moment to shine...and that moment is now. Freshly power washed and beautifully maintained, this furnished 4-bedroom, 3.5-bath home with minimal exclusions is ready for its next chapter. Nestled on a quiet cul-de-sac in Glen Riddle, it offers the perfect combination of comfort, privacy, and convenience—just minutes from Ocean City, Assateague Island, golf, dining, shopping, and everything the Eastern Shore has to offer. Step inside to soaring cathedral ceilings, an open-concept floor plan, two spacious primary suites, and a versatile loft ideal for guests, a home office, or additional living space. Whether you're searching for a primary residence, vacation getaway, or retirement retreat, this home is designed to fit your lifestyle from day one. Even better, many of the big-ticket updates have already been completed for you, including the roof, HVAC system, water heater, LED lighting, driveway maintenance, and more—giving you peace of mind and allowing you to focus on enjoying your new home and coastal lifestyle. With a **$25,000 price improvement**, this home has been strategically repositioned to offer exceptional value in one of the Eastern Shore's most sought-after golf course communities. If you've toured this home before, it's worth another look. If you've been waiting for the right opportunity in Glen Riddle, this is the one. **Fresh Look. Fresh Price. Fresh Opportunity. Don't miss your chance to make this beautiful home yours!**

10103 War Admiral Ln, Berlin

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty-WOC. Contact: 4105202600

$3,900,000
6 Beds 6 Baths
Most waterfront properties give you a view. This one gives you an entire Peninsula. Set on 6.39 private acres in the prestigious South Point Farms community, this extraordinary waterfront estate offers more than 700 feet of direct bayfront and a setting that feels worlds away from everything, yet minutes from the best of the Eastern Shore. Properties like this are not simply waterfront. They are surrounded by it. From its rare peninsula-style position, the estate captures sweeping, unobstructed water views in nearly every direction. Sunrises over the bay. Evening light reflecting across open water. Quiet mornings where the only sound is the tide moving along the shoreline. The custom built property was designed to blur the line between indoor comfort and outdoor living. Anchoring the estate is a 4,165 square foot main residence, thoughtfully positioned to take full advantage of the panoramic waterviews and endless skyline. Inside, nearly every room faces the bay. Soaring ceilings frame a grand great room with a traditional fireplace, while the chef’s kitchen, dining area, and sitting spaces flow naturally toward the surrounding decks and water views. The main-home offers four bedrooms, four and a half baths, two dedicated home offices, and multiple gathering spaces designed for both everyday living and large waterfront entertaining. Step outside and the experience continues. IPE Brazilian hardwood decks stretch along the waterfront side of the home, creating an ideal setting for sunset dinners, crab feasts, and long summer evenings overlooking the bay. A thoughtfully placed bay-facing 'bonus' garage provides convenient storage for boating gear, waterfront equipment or a perfect place for a home gym. Just steps away from the main-house is the 1,619 square foot guest-home, creating a private retreat for visiting family and friends. Two bedrooms, a full bath with sauna, a vaulted wood ceiling family room with fireplace, and a professional-grade kitchen allow guests to settle in comfortably for extended stays. The guest house overlooks the estate’s 50' x 24' bay-facing in-ground pool, where wide water views become the perfect backdrop for both relaxing and entertaining. A fully conditioned oversized-garage and game room adds another layer of entertainment space and is attached to the back of the guest house. For boaters, the waterfront infrastructure is equally impressive. A 250 foot private pier extends into the bay, providing quick access to open water, with more than enough room for your boat and your wave-runners. More than 700 feet of newly installed rip-rap shoreline protects the property while preserving its natural beauty. The grounds themselves are as memorable as the waterfront. Professionally landscaped acreage surrounds the home, highlighted by a half-acre deep-water pond, expansive lawn areas, and a circular drive that creates a grand yet welcoming arrival. And while the estate feels remarkably private, the location keeps you connected to the region’s most celebrated destinations. Assateague Island National Seashore is just minutes away, offering protected beaches, wild ponies, and miles of untouched coastline. The shops, restaurants, and charm of Historic Downtown Berlin, consistently ranked among America’s best small towns, are nearby. And when you want the energy of the coast, the beaches, boardwalk, and marinas of Ocean City are only a short drive away. Waterfront estates of this scale, privacy, and peninsula positioning rarely become available in Worcester County, or anywhere on Marylands Eastern Shore. Especially not with this combination of acreage, infrastructure, and proximity to the coast. For those who understand what a property like this represents, it is more than a home. It is a legacy waterfront setting that simply cannot be recreated.

5711 Waterside Dr, Berlin

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400

$419,990
4 Beds 2 Baths
Immaculate 4BR/2BA home - Custom built by local builders in 2023 in sought-after Jenkin's Orchard community. Large .7 acre lot backing to trees. Welcoming exterior features a handsome stone foundation on 3 sides, covered porch. Wide open concept floor plan, 9' ceilings, with a large dining area and family room. Dream kitchen - wood cabinets with moulding, upgraded granite countertops, oversized island, stainless-steel appliance package, pantry. Spacious primary bedroom boasts 2 walk-in closets, full, en-suite bath -- custom tile shower w/bench and tile niche, extended double-sink vanity with granite counters. 2 additional first floor bedrooms. A 2nd full bath with granite counters and a tub/shower combo, LVP flooring. Laundry room w/ storage area leads into the oversize 2-car garage. 2nd floor houses the 4th bedroom / flex space.Incredible location - across the street from Newtown Park and Recreation area - 2mi to Historic Downtown Pocomoke - a charming small town with rich history, art scene, boutique shops - even its own movie theatre - public parks and boat docks, & unique restaurants on the banks of the Pocomoke River. Location qualifies for 100% Financing! 19mi to NASA Wallops Facility, 19mi to beloved Chincoteague Island, and the incredible wild horses and sandy Atlantic beaches of Assateague. Close to everything Worcester County has to offer - boating, world-class fishing, crabbing, wildlife estuaries, incredible state parks - a true paradise for nature lovers, photographers, boaters - anyone who wants to enjoy the more relaxed pace of the Eastern Shore. Just 2-3 hours to major metro areas - Virginia Beach/Norfolk, Washington DC, Baltimore, Philadelphia, NYC. Life in Worcester County is good - from the beaches to the bays & beyond! Sizes, taxes are approximate.

2054 Groton Rd, Pocomoke City

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$648,500
5 Beds 3 Baths
Welcome to your dream home with stunning bay views from three sides! This beautifully updated single-family home offers a perfect blend of modern comfort and breathtaking scenery. Step inside to find an inviting open floor plan, featuring newly installed luxury vinyl plank flooring on the main level, new carpet upstairs and fresh, new paint throughout the entire house. With 5 bedrooms and 2.5 full baths, this home has great space! The heart of the home is the open main level with an updated kitchen, with quartz countertops and ample cabinet space. The bathrooms have also been tastefully renovated. Outside, enjoy the convenience of an oversized one-car garage with built in shelving for storage and ample outdoor space along with a beachy area to soak in the panoramic bay views. New roof and water heater both replaced Summer 2023. This home is a rare find, combining modern updates with a picturesque setting—don't miss the opportunity to make it yours!

13022 Wilson Ave, Ocean City

Listing courtesy of RE/MAX Realty Centre, Inc.. Contact:

$557,500
3 Beds 2 Baths
Opportunity knocks! The home is in need of some work as you will see upon entering, but it has potential for many things. Situated on an oversized corner lot with water views from three sides, this property offers room to add 2+ levels, as zoning laws allow building up to 45 feet. Zoned R-3 for multi-family and residential. Approved variances are in hand, including a variance for a second and third floor cantilever, making expansion plans even more attainable. Variance for an auxiliary dwelling unit (ADU) also in hand. If necessary, the current owner is open to a joint venture to see the project through to the finish line. Ideal for an investor looking to make a profit or someone looking to build a primary residence, a vacation getaway, an investment opportunity—or all of the above!

13444 Madison Ave, Ocean City

Listing courtesy of RE/MAX Realty Centre, Inc.. Contact: