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$3,195,000

Oceanfront living takes center stage at this inviting residence in Ocean Point, a private section of the prestigious Port Royal community on Hilton Head Island. Set along the Atlantic, the home enjoys an exceptional coastal setting, with the oceanfront property between the residence and beach maintained by Ocean Point-providing owners the beauty of this remarkable landscape without the responsibility of maintaining it themselves.Inside, the home offers a comfortable blend of classic character and refreshed coastal style, with spacious living areas designed to complement the spectacular setting. Warm heart-of-pine floors, a natural connection between the kitchen and Carolina Room, and multiple bedrooms with ocean views create an inviting island retreat. The first-floor primary suite offers a private escape, while generous gathering spaces are ideal for family and entertaining.Ocean Point owners enjoy a private pool immediately adjacent to the property, as well as exclusive beach access. Port Royal's exceptional amenities add even more to the lifestyle, including an oceanfront Olympic-size pool, Beach House, playground, fire pits, pickleball and tennis courts, leisure trails, and private security.Thoughtfully refreshed and beautifully appointed, this special oceanfront residence offers a rare opportunity to enjoy the best of Hilton Head Island-where the ocean, exceptional amenities, and relaxed coastal living are right outside your door.

4 Beds ⋅ 4 Baths ⋅ 3,300 SqFt. ⋅ HILTONHEAD-511945 MLS

Oceanfront living takes center stage at this inviting residence in Ocean Point, a private section of the prestigious Port Royal community on Hilton Head Island. Set along the Atlantic, the home enjoys an exceptional coastal setting, with the oceanfront property between the residence and beach maintained by Ocean Point-providing owners the beauty of this remarkable landscape without the responsibility of maintaining it themselves.Inside, the home offers a comfortable blend of classic character and refreshed coastal style, with spacious living areas designed to complement the spectacular setting. Warm heart-of-pine floors, a natural connection between the kitchen and Carolina Room, and multiple bedrooms with ocean views create an inviting island retreat. The first-floor primary suite offers a private escape, while generous gathering spaces are ideal for family and entertaining.Ocean Point owners enjoy a private pool immediately adjacent to the property, as well as exclusive beach access. Port Royal's exceptional amenities add even more to the lifestyle, including an oceanfront Olympic-size pool, Beach House, playground, fire pits, pickleball and tennis courts, leisure trails, and private security.Thoughtfully refreshed and beautifully appointed, this special oceanfront residence offers a rare opportunity to enjoy the best of Hilton Head Island-where the ocean, exceptional amenities, and relaxed coastal living are right outside your door.

13 Ocean N Point, Hilton Head Island

Listing courtesy of Charter One Realty.

$2,750,000

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.

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

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.

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

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.

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

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.

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.