5711 Waterside Dr, Berlin, MD 21811

A Rare Opportunity to Own an Exceptional Waterfront Estate. Nestled in the prestigious South Point Farms community, this breathtaking 6.39-acre waterfront estate presents a once-in-a-lifetime opportunity to experience unparalleled luxury, privacy, and natural beauty. With its peninsula-style bayfront setting and an expansive 700 feet of direct waterfront, this property offers a truly unique waterfront lifestyle—one where history, tranquility, and modern conveniences converge to create the ultimate coastal retreat. Designed for effortless indoor-outdoor living, the estate features a magnificent main residence, a spacious guest house, and an oversized detached garage/work-shop, all perfectly positioned to capture sweeping, unobstructed views of the bay. Whether you're drawn to the peaceful serenity of a quiet morning by the water or the thrill of high-speed boating adventures, this property offers the best of all worlds. -- THE MAIN HOME, spanning an impressive 4,165 square feet, is a masterpiece of thoughtful design and elegant craftsmanship. Nearly every room is graced with panoramic water views, allowing you to fully immerse yourself in the beauty of the bay. The home features: Four spacious bedrooms and four and a half baths. A grand great room with soaring ceilings and a traditional fireplace. A professional chef’s kitchen. Two dedicated home offices. A sitting room and dining area that seamlessly blend comfort with sophistication An attached bay-facing garage, ideal for water toys and gear Multiple IPE Brazilian hardwood decks, perfect for soaking in the waterfront ambiance. A newly installed roof on both the main and guest houses. -- THE GUEST HOUSE: Just steps from the main house, a 1,619-square-foot guest house offers an additional retreat for family and friends. Featuring two bedrooms, a full bath with a sauna, a vaulted wood ceiling family room with a fireplace, and a professional-grade kitchen with a breakfast bar, this space is ideal for hosting guests in comfort and style. Overlooking the shimmering 50’ x 24’ bay-facing in-ground pool, the guest house serves as a private sanctuary & guest oasis. Unwind in the fully-conditioned Guest House garage & game room, complete with pool table and more. UNMATCHED OUTDOOR AMENITIES: For those who love life on the water, this estate is a dream come true. A 250-foot pier/dock provides ample space for mooring boats (with a lift) offering quick access to the bay. Over 700 feet of newly installed rip-rap along the shoreline ensures years of worry free waterfront living. ADDITIONAL OUTDOOR HIGHLIGHTS: A large spa-inspired outdoor pool-side full-bath, perfect for rinsing off after a day on the water Beautifully landscaped grounds featuring a half-acre pond A spacious IPE wood deck ideal for crab feasts and alfresco dining A circular driveway providing a grand entrance to the estate THE BEST OF ALL WORLDS: Serenity, Convenience, and Adventure While this estate offers a private, peaceful escape, it is also ideally situated near some of the Eastern Shore’s most beloved destinations. Just minutes away, Assateague Island National Seashore awaits with its pristine beaches, wild ponies, and breathtaking coastal scenery, offering a nature lover’s paradise. The historic charm of Downtown Berlin, named America’s Coolest Small Town, is also close by, featuring boutique shopping, fine dining, and vibrant cultural events. For those seeking excitement, the bustling beaches and boardwalk of Ocean City are just a short drive away, providing endless entertainment, renowned restaurants, and world-class golf courses. A LEGACY OF COASTAL LUXURY: This estate is more than just a home—it is a rare and extraordinary opportunity to own a tasteful waterfront retreat that will never be matched. Whether you're looking for a luxurious year-round residence or a private coastal getaway, this exceptional property promises a lifetime of opportunity and enjoyment.