Ocean Side Port Royal Drive Homes with Clubhouse Association amenities

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

15 Fairway Winds Place, Hilton Head Island
$1,649,000
4 Beds ⋅ 5 Baths ⋅ 2,985 SqFt. ⋅ HILTONHEAD-513942 MLS
Beautіful lagoon‐tο-gοlf vіеws ѕеt the scene for thiѕ stуlishly updated home, just a short walk from the beach in Port Royal Plantation. A walled courtyard entry creates a welcoming sense of privacy, while approximately 3,000 square feet offers four bedrooms, four-and-a-half baths, and generous spaces for everyday living and hosting guests. The main level invites relaxed coastal living, with welcoming spaces for gathering, sharing meals, and hosting guests, complemented by the convenience of two downstairs bedrooms. Upstairs, two additional bedrooms and a spacious second living area provide a comfortable retreat for family and friends. A large deck overlooking the lagoon and golf course extends the living space outdoors-an inviting setting for entertaining, leisurely dinners, and quiet mornings. Offered furnished, this turnkey property is ready for immediate enjoyment. Low-maintenance grounds allow more time to enjoy the beach, community pool, Beach House, and leisure paths. Port Royal Plantation is a private, gated, residential-only community, with no resort or short-term rentals within its gates.

15 Fairway Winds Place, Hilton Head Island

Listing courtesy of Keller Williams Realty.

6 Drayton Place, Hilton Head Island
$2,699,000
4 Beds ⋅ 5 Baths ⋅ 4,075 SqFt. ⋅ HILTONHEAD-512097 MLS
The Art οf Port Roуаl Lіvіng.Dіsсοver the understated luxurу of lіfe in Port Royal. Ideally positioned just steps from private beach access, this exceptional 4-bedroom residence offers more than 4,000 square feet of refined coastal living on a beautiful .35-acre setting.With its sought-after second-row location, generous proportions, and effortless connection to the beach, 6 Drayton Place offers a rare opportunity to experience the best of Hilton Head Island-privacy, space, and the beach lifestyle, all without the oceanfront premium.A distinctive Port Royal offering for those who appreciate location, lifestyle, and timeless coastal living.

6 Drayton Place, Hilton Head Island

Listing courtesy of Engel & Volkers.

4 Middleton Place, Hilton Head Island
$3,740,000
3 Beds ⋅ 3 Baths ⋅ 2,733 SqFt. ⋅ HILTONHEAD-511980 MLS
JUST RΕDUCED! Own a ріeсе οf Hіltοn Head Island's οcеanfront-a rare opportunity at this price in coveted Port Royal Plantation. Opportunities like this do not come along often. With sweeping Atlantic views, magnificent live oaks, and an exceptional beachfront setting, this property deserves your attention now. Surrounded by mature natural landscaping, this private coastal retreat offers inviting spaces to enjoy today and exciting possibilities for the future. Enhance the existing home, explore expansion, or envision a new coastal estate that takes full advantage of this remarkable setting. The residence features 3 bedrooms and 2.5 baths, wide-plank pine floors, a beautifully renovated chef's kitchen, and walls of glass that bring the coastal landscape indoors. The half bath was originally a full bath, offering potential for restoration. An expansive rear deck sets the stage for entertaining, oyster roasts, morning coffee, and evenings overlooking the ocean. Designed by acclaimed architect Dean Winesett, whose work has appeared in Architectural Digest and Southern Living, the home was itself featured in Southern Living. Its distinctive Lowcountry architecture adds character and a notable history to this exceptional property. Enjoy a peaceful setting away from the island's resort corridor while remaining minutes from renowned dining, golf, and shopping. Port Royal Plantation prohibits short-term rentals, preserving its residential atmosphere. Private amenities for property owners and their guests include an oceanfront Beach House and swimming pool, tennis and pickleball courts, community gardens, leisure trails, and recreational and social activities. The price has changed. The extraordinary oceanfront setting remains. Schedule your private showing and discover the possibilities of owning your place on Hilton Head Island's beachfront.

4 Middleton Place, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS III brokered eXp Realty.

21 Barnacle Road, Hilton Head Island
$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.

20 N Port Royal Drive, Hilton Head Island
$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.

Start Your Search
board logo

We do not attempt to independently verify the currency, completeness, accuracy or authenticity of the data contained herein. It may be subject to transcription and transmission errors. Accordingly, the data is provided on an “as is” “as available” basis only and may not reflect all real estate activity in the market. © 2026 REsides, Inc. All rights reserved. Certain information contained herein is derived from information, which is the licensed property of, and copyrighted by, REsides, Inc.

How much is your home worth?

Get instant property value now!