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5711 Waterside Drive, Berlin, MD 21811

$3,900,000
  • 5711 Waterside Drive, Berlin, MD 21811 Main Photo

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BEDS6 BATHS5 full 1 partial SQUARE FEET6,312 MLS#MDWO2029066
STATUSACTIVE PROPERTY TYPEResidential - Single Family SUBDIVISIONSOUTH POINT FARMS SCHOOLWORCESTER COUNTY PUBLIC SCHOOLS

Property Description

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 Drive | MLS# MDWO2029066

This single family home located at 5711 Waterside Drive, Berlin, MD 21811 is currently listed for sale with an asking price of $3,900,000. This property was built in 1998 and has 6 bedrooms and 5 full and 1 partial baths with 6312 sq. ft. Waterside Drive is located in the SOUTH POINT FARMS subdivision within the WORCESTER COUNTY PUBLIC SCHOOLS school district. Search SOUTH POINT FARMS real estate on www.countonrick.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Central A/C
Fireplaces: 4
Fuel Type: Electric, Geo-thermal
Garage: 8
Heating: Forced Air
Home Style: Contemporary, Art Deco, Coastal
Lot Size: 6.39 Acres
Roof Type: Architectural Shingle
Stories: 2.5
Taxes: $13,929
Year Built: 1998

Feature Descriptions

Additional Structures: Above Grade, Below Grade
Appliances: Dishwasher, Dryer, Exhaust Fan, Oven - Double, Oven/Range - Electric, Range Hood, Refrigerator, Freezer, Stainless Steel Appliances, Washer
Building Name: NONE AVAILABLE
Exterior: Extensive Hardscape, Hot Tub, Outbuilding(s), Exterior Lighting, Lawn Sprinkler, Outside Shower, Private Beach, Other
Exterior: Frame
Fireplace: Gas/Propane, Stone, Wood
Flooring: Hardwood
Interior: 2nd Kitchen, Ceiling Fan(s), Kitchen - Gourmet, Kitchen - Island, Primary Bath(s), Primary Bedroom - Bay Front, Upgraded Countertops, Water Treat System, Wet/Dry Bar, Wood Floors, Stove - Wood, Sauna
Lake Name: Chincoteague Bay, Sinepuxent Bay, Newport Bay
Location: Bayfront
Lot: Cleared, Cul-de-sac, Front Yard, Landscaping, Pond, Poolside, Premium, Private, Rear Yard
Lot Dimensions: 6.39 Acre(S)
Parking Features: Circular Driveway, Paved Driveway, Private
Parking Notes: 14 Total Parking Spaces
Pet Restrictions: No Pet Restrictions
Sewer: Private Septic Tank
Special View Info: Bay, Other, Panoramic, Pond, Scenic Vista, Water
SQFT Above Finished: 6312
SQFT Total Finished: 6312
Structure Type: Detached
Swimming Pool: In Ground
Total Garage/Parking Spaces: 14
Water: Private/Community Water
Water Access: Fishing Allowed, Boat - Powered
Waterfront: Rip-Rap, Sandy Beach

Local Schools

School District: WORCESTER COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: Keller Williams Realty Delmarva
Agency Phone: 4105246400

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Estimated Payment

$ 10,977.96 per month $8,679.71 Principal & Interest $1,160.75 Property Tax $1,137.50 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 04/01/2026. The listing information on this page last changed on 04/01/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 04/01/2026 12:00:28 AM EST) or Bright MLS (last updated Tue 03/31/2026 11:49:52 PM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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