Hiltonheadbuy.com Search Results

$4,250,000

This exceptional Oceanfront home Designed by internationally acclaimed architect Dean Winesett, whose work has been featured in *Architectural Digest* and *Southern Living*, is a remarkable expression of timeless Lowcountry architecture. Also featured in *Southern Living*, the home showcases Winesett's signature style and craftsmanship, exemplified in several of his most celebrated residences throughout Hilton Head Island and Bluffton. Nestled beneath magnificent live oaks and surrounded by mature, natural landscaping, this private oceanfront retreat offers sweeping beach views and an unparalleled sense of serenity. 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 just minutes from Hilton Head's renowned dining, golf, shopping, and amenities. The thoughtfully designed residence features 3 bedrooms and 2.5 baths, with the existing 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 seamlessly connect to the surrounding landscape. An expansive rear deck provides the perfect setting for entertaining, oyster roasts, or simply enjoying the ocean breeze and breathtaking coastal views. Offering ample room for expansion, this property presents a rare opportunity to personalize and enhance an already extraordinary oceanfront estate. As one of Hilton Head Island's most exclusive residential communities, Port Royal Plantation prohibits short-term rentals, preserving the privacy, tranquility, and exceptional quality of life that make this oceanfront enclave one of the island's most desirable addresses. Exclusive to Port Royal property owners and their guests, the community's exceptional private amenities further elevate the lifestyle. Residents enjoy an oceanfront Beach House with a swimming pool overlooking the Atlantic, tennis and pickleball courts, community gardens, leisure trails, and a host of recreational and social amenities that make Port Royal one of the island's premier private communities.A rare architectural legacy, an irreplaceable beachfront setting, world-class private amenities, and endless possibilities combine to create one of the finest opportunities currently available on Hilton Head Island.

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

This exceptional Oceanfront home Designed by internationally acclaimed architect Dean Winesett, whose work has been featured in *Architectural Digest* and *Southern Living*, is a remarkable expression of timeless Lowcountry architecture. Also featured in *Southern Living*, the home showcases Winesett's signature style and craftsmanship, exemplified in several of his most celebrated residences throughout Hilton Head Island and Bluffton. Nestled beneath magnificent live oaks and surrounded by mature, natural landscaping, this private oceanfront retreat offers sweeping beach views and an unparalleled sense of serenity. 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 just minutes from Hilton Head's renowned dining, golf, shopping, and amenities. The thoughtfully designed residence features 3 bedrooms and 2.5 baths, with the existing 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 seamlessly connect to the surrounding landscape. An expansive rear deck provides the perfect setting for entertaining, oyster roasts, or simply enjoying the ocean breeze and breathtaking coastal views. Offering ample room for expansion, this property presents a rare opportunity to personalize and enhance an already extraordinary oceanfront estate. As one of Hilton Head Island's most exclusive residential communities, Port Royal Plantation prohibits short-term rentals, preserving the privacy, tranquility, and exceptional quality of life that make this oceanfront enclave one of the island's most desirable addresses. Exclusive to Port Royal property owners and their guests, the community's exceptional private amenities further elevate the lifestyle. Residents enjoy an oceanfront Beach House with a swimming pool overlooking the Atlantic, tennis and pickleball courts, community gardens, leisure trails, and a host of recreational and social amenities that make Port Royal one of the island's premier private communities.A rare architectural legacy, an irreplaceable beachfront setting, world-class private amenities, and endless possibilities combine to create one of the finest opportunities currently available on Hilton Head Island.

4 Middleton Place, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS III brokered eXp Realty.

$2,500,000

Beautiful Ocean Views from Multiple Rooms. This exceptional 3rd-row Port Royal home offers an inviting blend of coastal elegance, spacious living, and an unbeatable location. Soaring ceilings and a thoughtfully designed floor plan create an open, airy atmosphere with excellent separation of living spaces. Features include an eat-in kitchen, spacious family room, formal living and dining rooms, and a conditioned Carolina room for year-round enjoyment.Just steps from the Port Royal Beach Club, oceanfront pool, and beach access, this home offers the convenience of premier community amenities without the maintenance of a private pool. Port Royal is one of Hilton Head Island's most sought-after private oceanfront communities, featuring gated security, beach access, pickleball and tennis courts, and scenic leisure trails and more. Optional membership to the Port Royal Golf Club provides access to championship golf, tennis & dining. To preserve the community's peaceful residential character, short-term rentals are not permitted.

4 Beds ⋅ 5 Baths ⋅ 3,508 SqFt. ⋅ HILTONHEAD-511633 MLS

Beautiful Ocean Views from Multiple Rooms. This exceptional 3rd-row Port Royal home offers an inviting blend of coastal elegance, spacious living, and an unbeatable location. Soaring ceilings and a thoughtfully designed floor plan create an open, airy atmosphere with excellent separation of living spaces. Features include an eat-in kitchen, spacious family room, formal living and dining rooms, and a conditioned Carolina room for year-round enjoyment.Just steps from the Port Royal Beach Club, oceanfront pool, and beach access, this home offers the convenience of premier community amenities without the maintenance of a private pool. Port Royal is one of Hilton Head Island's most sought-after private oceanfront communities, featuring gated security, beach access, pickleball and tennis courts, and scenic leisure trails and more. Optional membership to the Port Royal Golf Club provides access to championship golf, tennis & dining. To preserve the community's peaceful residential character, short-term rentals are not permitted.

14 Salt Spray Lane, Hilton Head Island

Listing courtesy of Charter One 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.

$1,850,000

Experience the best of Hilton Head living in this beautifully designed home within the highly sought-after Port Royal Community. Perfectly positioned directly across from the residents' beach path, the Atlantic Ocean is less than 0.3 miles away, making beach days part of everyday life.Thoughtfully designed with exceptional bedroom separation, this predominantly single-story home offers 4 bedrooms and 4 baths, including a guest suite above the garage that can be closed off from the main home offering comfortable space for extended family or homeowners. The welcoming floor plan features a gracious foyer, formal dining room, spacious living room with a fireplace, and an inviting kitchen with counter seating, a sun-filled breakfast nook, and an adjoining great room with a second fireplace. The screened porch and expansive deck overlook the 11th fairway of the Barony Course, creating a peaceful backdrop for relaxing or entertaining.The spacious primary suite offers a calm and restful setting with a walk-in closet, dual vanities, a soaking tub, a separate shower, and a water closet. Two additional ensuite guest rooms are privately situated in their own wing.Set on a generous 0.636-acre homesite with room for a pool, this 3,218-square-foot home is part of one of Hilton Head Island's premier residential communities, where short-term rentals are prohibited. Residents enjoy private beach access, an oceanfront beach house, leisure trails, tennis, pickleball, gardens, 24-hour security, and optional membership to the Port Royal Golf Club.

4 Beds ⋅ 4 Baths ⋅ 3,218 SqFt. ⋅ HILTONHEAD-511500 MLS

Experience the best of Hilton Head living in this beautifully designed home within the highly sought-after Port Royal Community. Perfectly positioned directly across from the residents' beach path, the Atlantic Ocean is less than 0.3 miles away, making beach days part of everyday life.Thoughtfully designed with exceptional bedroom separation, this predominantly single-story home offers 4 bedrooms and 4 baths, including a guest suite above the garage that can be closed off from the main home offering comfortable space for extended family or homeowners. The welcoming floor plan features a gracious foyer, formal dining room, spacious living room with a fireplace, and an inviting kitchen with counter seating, a sun-filled breakfast nook, and an adjoining great room with a second fireplace. The screened porch and expansive deck overlook the 11th fairway of the Barony Course, creating a peaceful backdrop for relaxing or entertaining.The spacious primary suite offers a calm and restful setting with a walk-in closet, dual vanities, a soaking tub, a separate shower, and a water closet. Two additional ensuite guest rooms are privately situated in their own wing.Set on a generous 0.636-acre homesite with room for a pool, this 3,218-square-foot home is part of one of Hilton Head Island's premier residential communities, where short-term rentals are prohibited. Residents enjoy private beach access, an oceanfront beach house, leisure trails, tennis, pickleball, gardens, 24-hour security, and optional membership to the Port Royal Golf Club.

108 S Port Royal Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

$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.