Ocean Side Port Royal Drive Homes with Clubhouse Association amenities

Welcome to Ocean Side Port Royal Drive, a hidden gem nestled in the heart of Hilton Head Island, South Carolina. This picturesque community is perfect for those seeking a blend of coastal charm and modern conveniences. With its lush landscapes and serene surroundings, Ocean Side Port Royal Drive offers a tranquil retreat just minutes away from the vibrant activities that Hilton Head has to offer.

As you explore this delightful neighborhood, you’ll discover a variety of beautifully designed homes that cater to diverse tastes and lifestyles. Many of these residences boast stunning architectural details, spacious layouts, and inviting outdoor spaces, making them perfect for family gatherings or quiet evenings under the stars. The community is well-known for its Clubhouse Association amenities, which enhance the living experience for residents. Enjoy access to a well-appointed clubhouse, perfect for hosting events or social gatherings, as well as recreational facilities that encourage an active lifestyle.

Living in Ocean Side Port Royal Drive means you’re never far from the pristine beaches that Hilton Head is famous for. Whether you enjoy sunbathing, swimming, or beachcombing, you’ll find your slice of paradise just a short stroll away. Additionally, the community is conveniently located near shopping, dining, and entertainment options, ensuring that you have everything you need within reach.

Experience the perfect blend of relaxation and recreation in Ocean Side Port Royal Drive, where every day feels like a vacation. Come discover your dream home in this enchanting Hilton Head Island community!

Newest Ocean Side Port Royal Drive Homes with Clubhouse Association amenities

$2,750,000

4 Beds ⋅ 5 Baths ⋅ 4,075 SqFt. ⋅ HILTONHEAD-512097 MLS

Welcome to a truly special island retreat in prestigious Port Royal on Hilton Head Island. This 4-bedroom, 3-full-bath, 2-half-bath West Indies-inspired home captures the essence of relaxed coastal luxury, with timeless architecture and an effortless sense of place. Just steps away from private beach access, it offers the perfect setting for barefoot mornings, sunset gatherings, and unforgettable days by the sea. A rare opportunity to experience the beauty, privacy, and laid-back elegance of Hilton Head Island at its finest.

6 Drayton Place, Hilton Head Island

Listing courtesy of Engel & Volkers.

$3,950,000

3 Beds ⋅ 3 Baths ⋅ 2,733 SqFt. ⋅ HILTONHEAD-511980 MLS

Reimagine oceanfront living on one of Hilton Head Island's most exceptional beachfront properties. Set beneath magnificent live oaks and surrounded by mature natural landscaping, this private retreat offers sweeping ocean views, ample room for expansion, and the rare opportunity to renovate, enhance, or create a new coastal estate tailored to your vision. Ideally positioned in the most coveted section of Port Royal Plantation, the property enjoys a peaceful setting away from the island's resort corridor while remaining minutes from renowned dining, golf, shopping, and amenities. The expansive rear deck is perfectly suited for entertaining, oyster roasts, or simply enjoying the ocean breeze and breathtaking coastal views. The existing residence offers 3 bedrooms and 2.5 baths, with the half bath easily converted back to its original full-bath configuration. Wide-plank pine floors, a beautifully renovated chef's kitchen, and walls of glass create warm, inviting interiors that connect seamlessly with the surrounding landscape. Adding to the property's distinction is its remarkable architectural history. Designed by internationally acclaimed architect Dean Winesett, whose work has appeared in *Architectural Digest* and *Southern Living*, the home was also featured in *Southern Living* and reflects his signature Lowcountry style and craftsmanship. Port Royal Plantation prohibits short-term rentals, preserving the privacy, tranquility, and exceptional quality of life that define this exclusive oceanfront community. Private amenities reserved for property owners and their guests include an oceanfront Beach House and swimming pool overlooking the Atlantic, tennis and pickleball courts, community gardens, leisure trails, and an array of recreational and social offerings. An irreplaceable beachfront setting, celebrated architectural legacy, exceptional private amenities, and endless possibilities combine to create one of the most compelling oceanfront opportunities currently available on Hilton Head Island.

4 Middleton Place, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS III brokered eXp Realty.

$5,500,000

4 Beds ⋅ 5 Baths ⋅ 3,590 SqFt. ⋅ HILTONHEAD-511537 MLS

Oceanfront Luxury in a Private Gated Community on Hilton Head Island. Experience the ultimate in coastal living with this exceptional oceanfront residence, perfectly positioned within one of Hilton Head Island's most private gated communities. Offering breathtaking Atlantic Ocean views, direct beach access, and thoughtfully designed living spaces, this remarkable home is the perfect blend of elegance, comfort, and Lowcountry charm. Designed for both everyday living and effortless entertaining, the home features four spacious bedrooms, including two luxurious primary suites, five full bathrooms, and two separate living areas, providing exceptional flexibility for family and guests. The light-filled main living area showcases soaring vaulted ceilings, expansive windows, a fireplace, and walls of glass that frame spectacular ocean views. Enjoy relaxing on the upstairs deck allowing you to enjoy the sights and sounds of the Atlantic from nearly every angle. The generous primary suites offer private retreats complete with spa-inspired baths and tranquil coastal vistas. The first floor living area also offers a fireplace. Stroll outside to a private pool, expansive patio, lush tropical landscaping, and a private walk leading directly to one of Hilton Head Island's most pristine beaches create an unparalleled outdoor experience. Towering live oaks provide timeless Lowcountry character while preserving privacy and natural beauty. Whether you're seeking a luxurious primary residence, a second home, or an extraordinary oceanfront retreat, this exceptional property delivers the rare combination of privacy, sophistication, and direct beachfront living in one of Hilton Head Island's most coveted locations.

21 Barnacle Road, Hilton Head Island

Listing courtesy of Hilton Head Real Estate Partners.

$6,500,000

3 Beds ⋅ 5 Baths ⋅ 5,725 SqFt. ⋅ HILTONHEAD-502804 MLS

Spectacular must-see modern and dramatic Wayne Windham designed oceanfront estate in residential Port Royal. This gorgeous home offers a flexible floor plan with a gourmet kitchen and great room, 3-4 bedroom suites, and endless extra living areas to accommodate an office, children's area, game tables, piano room, work-out room, you name it! Perfect for family living as well as entertaining! Located on a prime ocean view lot, this home has been lightly lived in. Professional landscaping, free-standing columns, dramatic sweeping twin staircases, saturnia inlayed flooring, Vitricore kitchen cabinets, fireplace, glass brick walls, infinity pool, are just some of the upscale appointments of this light-filled masterpiece.

20 N Port Royal Drive, Hilton Head Island

Listing courtesy of Sea Pines Real Estate South Beach.

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