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6 Overlook Pl, Hilton Head Island
$7,050,000
6 Beds ⋅ 9 Baths ⋅ 7,789 SqFt. ⋅ HILTONHEAD-453976 MLS
Unobstructed ocean views define this 1.16-acre Hilton Head Island estate cocooned in the privacy of a double lot. Designed for both quiet comfort and large-scale entertaining, noteworthy features include a temperature-controlled wine cellar for 1,000 bottles, an outdoor sports area with basketball, bocce, and shuffleboard, a beachfront putting green, a resort-style pool, and an outdoor kitchen. High ceilings and boundless windows allow for serene ocean vistas from the home's grand interiors, while coffered ceilings add to its timeless luxury. Complete with a temperature-controlled four-bay garage - this is the home for a true collector.

6 Overlook Pl, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty. Selling Office: Keller Williams Realty.

16 Planters Row, Hilton Head Island
$6,800,000
5 Beds ⋅ 6 Baths ⋅ 4,622 SqFt. ⋅ HILTONHEAD-503236 MLS
Experience unparalleled oceanfront luxury in the exclusive, private community of Port Royal on Hilton Head Island. This impeccably crafted 5-bedroom, 5.5-bath residence offers breathtaking panoramic Atlantic views and sophisticated coastal living at its finest. Built in 2010 and meticulously maintained, this home blends timeless architecture with modern elegance and exceptional construction quality. A grand foyer and soaring ceilings welcome you into open, light-filled living spaces designed to capture the beauty of the shoreline from nearly every room. Walls of glass frame sweeping ocean vistas, while refined interior finishes include custom millwork, stone and wood flooring, and luxurious designer details throughout. The chef's kitchen features premium appliances, a generous island, and seamless flow into multiple dining and gathering areas-ideal for both intimate living and entertaining. The primary suite is a serene retreat with stunning views, a spa-inspired bathroom, and ample closet space. Each guest suite offers privacy and comfort, with ensuite baths and refined appointments. Step outside to your private beachfront oasis, complete with an oceanside pool and spa, expansive terraces, outdoor living areas, and direct access to Hilton Head's pristine shoreline. Enjoy sunsets, sea breezes, and the tranquil sound of waves from beautifully designed outdoor spaces. This home has been thoughtfully updated and enhanced with a new 30-year roof installed in 2023, two tankless water heaters, HomeTeam in-wall pest control system, DogWatch invisible fencing, a home security system, multiple new HVAC systems, upgraded lighting, custom living room cabinetry, extended oceanside patio, refinished exterior surfaces, new mini-split in the finished garage room, new appliances, and numerous additional improvements completed between 2018-2025. Additional features include an elevator, multiple living and media spaces, an oversized 4-car garage, impact-rated windows, and exceptional storage throughout. Located on one of Port Royal's most sought-after oceanfront streets, this residence offers the rare combination of luxury, privacy, and direct beach access within a secure, gated oceanfront community. A true coastal masterpiece-crafted for those seeking exceptional oceanfront living on Hilton Head Island.

16 Planters Row, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC. Selling Office: Hilton Head Properties.

28 Planters Row, Hilton Head Island
$6,350,000
5 Beds ⋅ 7 Baths ⋅ 6,346 SqFt. ⋅ HILTONHEAD-450493 MLS
This rare oceanfront opportunity sits in one of Hilton Head’s premier gated communities, offering direct access to the island’s finest beaches. Surrounded by pristine dunes and open space, the home features a private path leading directly to the sand. Designed with exquisite woodwork and fine craftsmanship, the home’s expansive interior has been lightly used as a secondary residence, ensuring exceptional condition. Enjoy breathtaking ocean views and stunning sunrises, embracing a coastal lifestyle. This property provides an unparalleled opportunity to own a refined oceanfront escape in one of Hilton Head’s most exclusive enclaves.

28 Planters Row, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty. Selling Office: Maxey Blackstream Christie's International Real Estate.

4 Heyward Place, Hilton Head Island
$2,990,000
5 Beds ⋅ 7 Baths ⋅ 4,417 SqFt. ⋅ HILTONHEAD-502592 MLS
Custom-built to the highest standards by Steve Dill Builders, this luxurious ocean home in Port Royal defines refined coastal living on Hilton Head Island. Every element was curated for craftsmanship and comfort - from the Andersen impact windows and cement board exterior to interior finishes of oil-rubbed European oak floors, marble and granite surfaces, and artisan woodwork throughout-groove ceilings, poplar shiplap walls, Chicago brick, Italian tile, and a custom-commissioned chandelier create a timeless, coastal-modern aesthetic. The open living plan blends natural light and seamless flow, anchored by a chef's kitchen featuring an induction cooktop, double ovens, wine cooler, and Sub-Zero refrigeration. Each bedroom offers an en-suite bath, while multiple outdoor spaces invite year-round entertaining - including a private bocce court and sunlit terraces framed by lush landscaping. Just three homes back from the ocean, this residence pairs enduring architecture with the serenity of Hilton Head's most private beachfront community - where design, detail, and setting come together in perfect coastal harmony.

4 Heyward Place, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty. Selling Office: Keller Williams Realty.

5 Princeton Circle, Hilton Head Island
$2,725,000
5 Beds ⋅ 6 Baths ⋅ 3,452 SqFt. ⋅ HILTONHEAD-501940 MLS
Nestled within the sea breezes of Port Royal Sound, this exceptional 5-bedroom home sits within the private, gated community of Port Royal, just a short stroll from the pristine beach. The interiors are bright and inviting, with abundant windows that fill the space with natural light. White oak accents, designer lighting, and a kitchen featuring striking black marble countertops blend effortlessly to create a serene, modern coastal vibe. Every detail has been thoughtfully curated for comfort and convenience, from automatic blinds to a whole-house generator and EV charger. Step outside to a beautifully designed covered patio with a private splash pool and hot tub, where built-in music and seamless indoor-outdoor flow create the perfect setting for entertaining or relaxing in shaded comfort. Beyond the property, enjoy the best of Port Royal living with a newly renovated beach club, two championship golf courses, tennis and pickleball courts, and miles of scenic leisure trails.

5 Princeton Circle, Hilton Head Island

Listing courtesy of RE/MAX Island Realty. Selling Office: Charter One Realty.

65 N Port Royal Drive, Hilton Head Island
$2,600,000
5 Beds ⋅ 6 Baths ⋅ 4,677 SqFt. ⋅ HILTONHEAD-502346 MLS
Step into an extraordinary coastal lifestyle with this spectacular Kermit Huggins custom designed residence that offers an expansive floor plan with five bedrooms, that include two primary suites, four full baths and two half baths and is perfectly positioned across the street from the beach and on a private golf course setting; two additional rooms serve as a media room and a cozy morning/reading room. The magnificent lanai with balcony, spiral staircase, fireplace and Lynx built-in grill provides a seamless transition from the interior to your private oasis.The grand live oaks and magnolias welcome you into the gated courtyard entrance to this meticulously maintained home with high-end finishes. This home offers a rare blend of exclusive seaside living and tranquil, resort style amenities, making it a sanctuary for luxury and leisure. Features include new 2023 and 2024 HVAC systems, new Subzero refrigerator, custom closets, whole house Aquasana water filtration system, newer metal roof, epoxy with urethane finished garage floors and electric vehicle H/U Level 2, Port Royal offers private beach access, a stunning beach house, pool, fire pits, tennis and pickle ball courts, playground, leisure trails, community gardens, farm plots and gated 24-hour security; Port Royal is the only Hilton Head private oceanfront community with no short-term rentals and no commercial activity. The optional country club membership offers a clubhouse with dining, golf, pickle ball and tennis.

65 N Port Royal Drive, Hilton Head Island

Listing courtesy of Carolina One MPN. Selling Office: ELEVE PROPERTIES Brokered by EXP Realty.

20 Royal Crest Drive, Hilton Head Island
$2,425,000
4 Beds ⋅ 5 Baths ⋅ 3,400 SqFt. ⋅ HILTONHEAD-503048 MLS
Hilton Heads only private oceanfront community. Custom-built by a local premier builder, this 4BR/4.5BA residence blends timeless craftsmanship w modern innovation. Approx. 3,400 sq. ft., the home lives large soaring ceilings, abundant light & an open layout designed for gathering. A welcoming foyer leads to flexible spaces including a dining/sitting room, a living room w stacked-stone fireplace, & a gourmet kitchen w gas range, counter seating & casual dining overlooking the pool & covered patio. The primary suite is privately set apart from two guest rooms, with a 4th upstairs. Heated and cooled resort style pool. The insulated, climate-controlled 3-car garage with epoxy floor. Modern upgrades include a Tesla Power Wall III, backup generator, & future-ready solar design. Port Royal offers unmatched amenities private beaches, oceanfront pool, tennis, pickleball, leisure trails, and 24-hour security. In a community where opportunities like this are rare, this residence sets the benchmark for Port Royal living truly best in class!

20 Royal Crest Drive, Hilton Head Island

Listing courtesy of Realty One Group - Lowcountry. Selling Office: Engel & Volkers.

8 Royal Crest Drive, Hilton Head Island
$2,412,500
4 Beds ⋅ 4 Baths ⋅ 4,886 SqFt. ⋅ HILTONHEAD-454929 MLS
One-of-a-kind European-inspired estate in Port Royal, Hilton Head’s only private oceanfront community. This rare brick home (hand-painted for a modern coastal look) blends Old World charm w/ coastal elegance. Renovated in 2017 & 2022, it offers 4BR+ flex rooms, living room w soaring ceilings & fire place, TV room, coffee nook, dining rm w/ fireplace, art studio & gourmet kitchen. Two upstairs BR suites + loft. Heated pool, fenced flagstone patio & lush .66-acre lot create a private oasis. Imagine morning swims, coastal breezes & evenings under the stars—your dream Lowcountry life starts here.

8 Royal Crest Drive, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Charter One Realty.

24 Scarborough Head Road, Hilton Head Island
$2,375,000
4 Beds ⋅ 5 Baths ⋅ 3,106 SqFt. ⋅ HILTONHEAD-504638 MLS
Built in 2020 and maintained to the highest standard, this custom Port Royal residence offers exceptional quality, thoughtful design, & effortless livability. Situated on a rare .77-acre homesite overlooking the 11th fairway of the Barony Course, the setting is both private and picturesque.The main level is designed for comfortable everyday living, featuring a serene primary suite w a spa-inspired bath, 2 beautifully appointed guest suites, a private office, and a well-planned laundry room. Upstairs, a spacious bonus bedroom w full bath provides ideal separation for guests or extended family.At the heart of the home, a gourmet kitchen with an oversized island, generous dining area, and beverage coolers opens seamlessly to the outdoors through collapsing doors. A screened porch, grill porch with rocking chairs, and an extraordinary backyard create a true indoor-outdoor lifestyle.The heated and cooled private pool, fire pit, and bocce court transform the .77-acre property into a personal retreat - perfect for quiet evenings or gathering with friends. This is a compelling opportunity in Port Royal, where lot acquisition and new construction would exceed this investment today.

24 Scarborough Head Road, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Charter One Realty.

4 Hartford Place, Hilton Head Island
$2,300,000
4 Beds ⋅ 6 Baths ⋅ 3,592 SqFt. ⋅ HILTONHEAD-510274 MLS
LOCATED in Port Royal the oceanfront private community on Hilton Head. ON A 1.3 ACRE LOT with massive live Oaks and TIDAL VIEWS FOR MILES toward PORT ROYAL SOUND. Natural landscape changes constantly with the tides, showing changing colors of the Spartina grass. This home offers unmatched quietness and privacy to allow you to unwind and escape the daily rush. See a wide variety of birds, marine life and other animals like being in a private nature sanctuary. Outdoor kitchen pool, and gazebo for the firepit overlooking tidal marsh out to Port Royal Sound. Large porch overlooking the pool and Pool power room. The main house has a Master & Three bedrooms.. A large quest suite over the three-car garage. The garage has GREAT storage and workspace. The updated kitchen opens to a large dining area. This area is connected to two large sitting areas overlooking the tidal marsh. The 3-car garage has all built-in storage and epoxy floors. A total of 4 bedrooms with 4 full baths and 2 half baths ( one is by the pool) If you ever wanted to enjoy nature, this is the perfect location.

4 Hartford Place, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Dunes Real Estate.

20 Royal Crest Drive, Hilton Head Island
$2,300,000
4 Beds ⋅ 5 Baths ⋅ 3,400 SqFt. ⋅ HILTONHEAD-501527 MLS
Experience refined coastal living in Port Royal, Hilton Heads only private oceanfront community. Custom-built by a local premier builder, this 4BR/4.5BA residence blends timeless craftsmanship w modern innovation. The current owners elevated it further by creating a resort-style heated & cooled pool and finishing the space over the garage into a private guest suite. Approx. 3,400 sq. ft., the home lives large w soaring ceilings, abundant light & an open layout designed for gathering. A welcoming foyer leads to flexible spaces including a dining/sitting room, a living room w stacked-stone fireplace, & a gourmet kitchen w gas range, counter seating & casual dining overlooking the pool & covered patio. The primary suite is privately set apart from two guest rooms, with a 4th upstairs.The insulated, climate-controlled 3-car garage with epoxy floor. Modern upgrades include a Tesla Power Wall III, backup generator, & future-ready solar design. Port Royal offers unmatched amenities private beaches, oceanfront pool, tennis, pickleball, leisure trails, and 24-hour security. In a community where opportunities like this are rare, this residence sets the benchmark for Port Royal living truly best in class!

20 Royal Crest Drive, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Realty One Group - Lowcountry.

33 N Port Royal Drive, Hilton Head Island
$2,220,000
4 Beds ⋅ 5 Baths ⋅ 3,972 SqFt. ⋅ HILTONHEAD-501097 MLS
Only 300 yards from the sand, this Port Royal home ensures the Beach is part of your everyday life. The custom floor plan pairs coastal ease with modern design, set on an oversized (.86 acre) corner lot w a golf view. Inside, soaring ceilings and an open inviting layout create a light-filled gathering space with fireplace, dining, kitchen, beverage bar, and walk-in pantry. A welcoming front room with fireplace, primary suite, office, guest room & laundry complete the main level. Upstairs, a split design offers three more guest suites, including a bunk room retreat perfect for family & friends. Outdoors, enjoy lush gardens, open & covered patios designed by master gardeners. Living in Port Royal means access to private beach access, a beach house, lap pool, fire pits, leisure trails, pickleball, tennis, playground, community gardens, and 24-hour security in Hilton Heads only private oceanfront community with no short-term rentals. A warm & social setting.

33 N Port Royal Drive, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Engel & Volkers.

43 Scarborough Head Road, Hilton Head Island
$2,200,000
4 Beds ⋅ 5 Baths ⋅ 3,400 SqFt. ⋅ HILTONHEAD-502464 MLS
In the heart of Hilton Head's only completely private oceanfront community, the streets gently wind through canopies of live oaks and the whisper of ocean air. In this island paradise sits a study in elegance, quality, and comfort: 43 Scarborough Head has been lovingly and tastefully reimagined with no expense spared, every inch refined to meet the highest standards of craftsmanship, comfort, and quiet sophistication. This single-level residence unfolds with a calm sense of grace and every day comfort, offering four ensuite bedrooms, an additional flexible studio, fitness room, or office space, and five full baths. Wide-plank white oak floors guide you through curated spaces that balance elegance with ease. The gourmet kitchen is a masterwork of form and function, artfully designed for the way life is actually lived... morning coffee at the island, slow evenings around the table, and effortless gatherings that flow from one perfect space to the next. Beyond the kitchen, the completely reimagined screened porch-turned-four-season room invites year-round living and connection, warmed by a flickering fireplace and framed by serene garden views through magnificent, large windows. Every element of the home - roof, gutters, pavers, landscape - has been renewed or replaced to exacting standards, a seamless blend of modern sensibility and enduring Lowcountry charm. Outdoors, lush front and rear lawns extend under dappled sunlight and ancient live oaks, a testament to meticulous care and a love of beauty in the details. And just beyond your doorstep, the beach is a short and scenic stroll away. Enjoy your very own stretch of Hilton Head's soft white sand, where mornings begin with sunrise strolls and evenings fade into the lilting waves. 43 Scarborough Head Road is not simply move-in ready; it's life-ready. Every finish, every choice, every gesture speaks of ease, refinement, and quality. Experience place, peace, and your invitation to inhabit the very best of Hilton Head Island living.

43 Scarborough Head Road, Hilton Head Island

Listing courtesy of ELEVE PROPERTIES Brokered by EXP Realty. Selling Office: Sea Pines Real Estate - Beach Club.

24 Ocean N Point, Hilton Head Island
$2,050,000
3 Beds ⋅ 4 Baths ⋅ 2,533 SqFt. ⋅ HILTONHEAD-455067 MLS
Welcome to 24 Ocean Point North a modern and stunning 2nd-row beach home in Port Royal! This home has been updated throughout with all new hardwood floors, renovated kitchen with a Thermador induction Range, Viking French door oven, and quartzite counters. The upgrades continue with a refreshed powder room, polyaspartic garage floor, automatic blinds, professional landscape/hardscape and so much more! Outside you’ll find a rare on Hilton Head Island enclosed backyard that provides an extra layer of privacy along with an expansive patio to sit and enjoy the sea breeze. Ocean Point offers exclusive amenities to its owners with a private community pool located just across the street and private beach access via a dedicated beach path.

24 Ocean N Point, Hilton Head Island

Listing courtesy of EXP Realty LLC. Selling Office: Charter One Realty.

111 Fort Walker Drive, Hilton Head Island
$2,000,000
4 Beds ⋅ 5 Baths ⋅ 4,250 SqFt. ⋅ HILTONHEAD-507929 MLS
150 STEΡS TO ΤΗE ΒΕΑCH! Τuсked within the privatе, oсeanfront community of Port Royal, this exceptional Lowcountry residence offers a rare combination of scale, setting, and timeless Southern character. 111 Fort Walker Drive presents an extraordinary opportunity to own a marshfront estate in one of Hilton Head Island's most sought-after enclaves. Set on an expansive 0.78-acre homesite, the property is framed by majestic live oaks draped in Spanish moss, creating a serene, shaded backdrop that defines true Lowcountry living. Sweeping marsh views extend beyond the backyard, where a private crabbing dock invites you to fully embrace the coastal lifestyle. With ample room to ADD A CUSTOM POOL, you can create your own private marshside oasis-an ideal setting for relaxing, entertaining, and enjoying breathtaking sunsets just steps from the beach.The home features 4 bedrooms and 5 bathrooms, thoughtfully designed to accommodate both everyday living and multi-generational needs. The grand primary suite is a standout, offering dual bathrooms, generous closet space, and dedicated sitting and office areas, providing both luxury and functionality rarely found in one residence. Originally renovated in 2006 and further enhanced in 2024, the home blends classic architectural elements with modern updates. An abundance of storage throughout ensures practicality without compromising design. Ideal for a large family, a legacy property, or those seeking space and privacy within a prestigious community, this offering captures the essence of refined Lowcountry living-where natural beauty, exceptional privacy, and an unparalleled coastal lifestyle converge. Just 150 steps from the beach, you'll enjoy the best of both worlds: tranquil marshfront living with effortless access to the Atlantic Ocean.

111 Fort Walker Drive, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS III brokered eXp Realty. Selling Office: William Raveis - Carolina LLC.

32 Doubloon Drive, Hilton Head Island
$1,840,000
3 Beds ⋅ 4 Baths ⋅ 3,218 SqFt. ⋅ HILTONHEAD-511942 MLS
Rarely dοes a hοmе offеr οnе-lеvеl living on nearly threе-quаrters of an acre with exceptional privacy, a five-minute walk to the beach, and a location within Port Royal-one of Hilton Head Island's most exclusive private, oceanfront communities. Every day feels like a vacation in this beautifully updated coastal retreat. Impeccably maintained and truly turnkey, this exceptional home features a flowing floor plan with soaring vaulted ceilings, oversized bedrooms, a private executive office adjoining the primary suite, fireplace, custom built-ins, and a chef's kitchen complete with a Wolf induction cooktop and oversized center island. The spacious primary suite is a retreat of its own, offering a generous spa-inspired bath with abundant space between two separate walk-in closets. Situated on a rare point lot at the end of a quiet cul-de-sac, the nearly -acre homesite has been thoughtfully transformed into a spectacular backyard oasis. Mature live oaks, lush landscaping, premium paver walkways, and a beautifully sized pool create a secluded, resort-like setting. The current owners intentionally designed the landscape to maximize privacy while preserving the unique opportunity for a future owner to selectively open portions of the landscaping and capture multiple golf course views. A rare offering where thoughtful design, resort-inspired privacy, and timeless Lowcountry living come together in one of Hilton Head Island's most exclusive private, oceanfront communities.

32 Doubloon Drive, Hilton Head Island

Listing courtesy of Dunes Real Estate. Selling Office: Premier Properties of Hilton Head Island.

9 Fort Walker Drive, Hilton Head Island
$1,750,000
4 Beds ⋅ 3 Baths ⋅ 2,791 SqFt. ⋅ HILTONHEAD-511036 MLS
Luxury Cοastal Ꮮіving, Cοmрlеtelу Rеimagined!! Welcomе to 9 Fοrt Walker Drive, an exceptional coastal residence in the prestigious gated community of Port Royal Plantation. Completely remodeled from top to bottom, this stunning 4-bedroom, 3-bath home blends timeless elegance with modern luxury, offering the rare opportunity to own a truly turnkey home in one of Hilton Head Island's most desirable communities. Situated on a private 0.6-acre golf course homesite, the property offers picturesque fairway views and ample space to create your dream backyard oasis, including room for a custom pool.Designed for effortless single-level living, the open floor plan is filled with natural light, soaring vaulted ceilings, and impeccable craftsmanship throughout. Wide-plank flooring, shiplap walls and ceilings, designer lighting, and refined architectural details create a sophisticated coastal aesthetic. The spacious great room is anchored by a striking acoustic fluted feature wall with a hidden door and sleek electric fireplace, creating an inviting focal point for everyday living and entertaining.The gourmet kitchen is a showpiece, featuring premium Bosch appliances, custom soft-close cabinetry, quartz countertops, and an oversized island designed for gathering with family and friends.The luxurious primary suite offers a custom walk-in closet and a spa-inspired bath with an oversized walk-through tile shower, dual oak vanity, quartz countertops, and designer finishes. Two additional bathrooms have been beautifully renovated with custom cabinetry, quartz surfaces, ceramic tile flooring, and tiled shower surrounds. Additional highlights include a thoughtfully designed laundry room with custom built-ins, abundant storage, and a rear deck with contemporary cable railings overlooking the golf course-the perfect place to enjoy morning coffee or evening sunsets.Every detail has been carefully curated with exceptional craftsmanship and high-end finishes, creating a home that lives like new while embracing the relaxed sophistication of coastal living. Home also features a new roof. Enjoy the unmatched lifestyle of Port Royal Plantation, with 24-hour gated security, a private oceanfront beach club, championship golf, tennis, pickleball, walking trails, and easy access to Hilton Head Island's finest dining, shopping, and marina.Simply move in and enjoy luxury coastal living at its finest.

9 Fort Walker Drive, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty. Selling Office: Collins Group Realty.

9 Tabby Road, Hilton Head Island
$1,750,000
3 Beds ⋅ 4 Baths ⋅ 4,015 SqFt. ⋅ HILTONHEAD-507770 MLS
Set beneath a majestic oak, this well-built 2013 home offers a sense of quiet presence and privacy that's increasingly rare. Overlooking the lagoon, the private fenced pool/spa and expansive covered patio-complete w/ outdoor fireplace, grill & sink create an inviting setting for relaxed days and memorable evenings. Inside, soaring ceilings and a thoughtfully designed open layout bring both space and comfort. The living room, centered around a stacked stone fireplace, flows easily into the dining area and a generous gourmet kitchen w/ gas range, center island & pot filler. Stacking doors open wide, allowing the indoors and outdoors to live as one-ideal for gathering, celebrating, or simply unwinding. Off the living room is a large office and powder room with the primary suite privately positioned in one wing of the house while 2 ensuite guest rooms and laundry/utility room are on the opposite side for comfort and separation. An expansive bonus room over the 3-car garage offers flexibility for guests, work, or recreation. Homes like this-offering space, quality, and a setting designed for both everyday living and entertaining-are not often found in Port Royal Plantation. Enjoy private beach access, oceanfront pools, clubhouse, tennis, pickleball, leisure trails, gardens & 24-hour security.

9 Tabby Road, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Charter One Realty.

3 Fairway Winds Place, Hilton Head Island
$1,750,000
4 Beds ⋅ 4 Baths ⋅ 2,531 SqFt. ⋅ HILTONHEAD-505119 MLS
On the ocean-facing side of Fairway Winds in Port Royal Plantation, this special property captures the very best of coastal living. Perfectly positioned on a glistening lagoon with sweeping golf views, the setting delivers constant breezes, beautiful morning sun, and easy proximity to the beach. It's a location that simply feels right.Designed as a true lifestyle home, the courtyard-style layout offers privacy and effortless outdoor living on a manageable lot. The stunning Ipe wood deck is the heart of it all - complete with a plunge pool and Sunbrella awnings - creating a resort-like retreat ideal for quiet mornings or relaxed evenings with friends.Inside, the home has been thoughtfully renovated and improved year after year- including windows, doors, and virtually every surface. The first floor features an open living and dining area anchored by a tabby fireplace, a beautifully appointed kitchen with center island, and a welcoming front den with a second fireplace. A full guest bath and laundry room add convenience, while the first-floor primary suite is a true sanctuary with dual vanities, custom closets, heated floors and towel warmers, zero-entry shower, and doors opening to the private deck. Upstairs, an ensuite guest room plus two additional bedrooms with a shared bath provide comfortable space for family and visitors.Lovingly maintained and beautifully cared for, this is a turnkey opportunity for someone looking to simplify without compromise - enough room to host, yet easy to maintain. Fairway Winds is known for its friendly atmosphere and close-knit feel, all within the exceptional amenities of Port Royal's private oceanfront community.

3 Fairway Winds Place, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Charter One Realty.

85 S Port Royal Drive, Hilton Head Island
$1,725,000
4 Beds ⋅ 4 Baths ⋅ 4,230 SqFt. ⋅ HILTONHEAD-505086 MLS
Second row in Port Royal Plantation - where proximity to the beach via a private path defines the lifestyle and the value. Just moments from the sand, this exceptional homesite offers the rare opportunity to own this close to the Atlantic within one of Hilton Head's most private oceanfront communities.The home has been comprehensively updated, including a new 2024 roof, fresh interior and exterior paint, renovated kitchen and baths, and updated flooring throughout. While fully improved, it still carries the warmth and character of a classic coastal residence. The original garage was thoughtfully converted into a heated and cooled media/leisure room, creating additional flexible living space (and may be converted back if desired). A circular drive enhances both curb appeal and ease of access.Second-row living in Port Royal includes private beach access, an oceanfront beach club, golf, tennis, pickleball, leisure trails, and 24-hour security - a combination of location and community that is increasingly rare.

85 S Port Royal Drive, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Charter One Realty.

30 Outpost Lane, Hilton Head Island
$1,685,000
5 Beds ⋅ 6 Baths ⋅ 4,913 SqFt. ⋅ HILTONHEAD-504157 MLS
Tucked within the private oceanfront community of Port Royal, this architecturally striking home is a rare blend of drama, warmth, and effortless livability. From the moment you arrive, mahogany double front doors set the tone, opening to a light-filled interior anchored by a floating staircase, skylights, and a stunning two-way fireplace connecting the main living spaces. Rich cherry flooring, smooth ceilings, crown molding, and custom cabinetry create a refined yet welcoming backdrop throughout.Designed for both everyday comfort and memorable entertaining, the open kitchen features stainless appliances, generous prep space, and seamless flow to the living and dining areas, complemented by a wet bar for easy gatherings. The main level offers two private suites and a large office, while the primary suite upstairs is a true retreat-cathedral ceilings, a dressing room, spacious closets, and a private balcony with stairs leading directly to the pool below. An additional guest suite and loft complete the second floor.A separate private guest residence offers exceptional flexibility, featuring its own living space, game room, bedroom, and bath-ideal for extended stays, visiting family, or multi-generational living. The oversized three-car garage includes heated and cooled storage, adding another layer of thoughtful design. Outside, the setting is just as special: a screened porch, fire pit, and a heated 65-foot pool invite year-round enjoyment on a beautifully sized .7-acre lot. 5BR / 5.5BA | 4,905 sq ft. A truly distinctive Port Royal offering-designed to impress, built to be lived in, and set in one of Hilton Head Island's most coveted oceanfront communities.

30 Outpost Lane, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Engel & Volkers.

3 Claire Drive, Hilton Head Island
$1,632,000
4 Beds ⋅ 4 Baths ⋅ 3,223 SqFt. ⋅ HILTONHEAD-501407 MLS
Tucked away on a quiet cul-de-sac in private, oceanfront Port Royal Plantation, this beautifully renovated 4BR home + media/office offers the perfect blend of relaxation & style. The owners transformed it into a true retreat adding a sparkling pool w/fenced patio, new timber tech deck, & fresh landscaping that feels like your own resort. Inside, enjoy airy spaces w/wood-look tile floors, remodeled baths, a media room/office, & a bonus rm w/full bath upstairs. Updates include new roof, windows, water heaters, AC, fireplace & more. Lagoon views add to the peaceful vibe in this special 3,223 sq ft home designed for fun & easy Low Country living.

3 Claire Drive, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: EXP Realty LLC.

22 Sovereign Drive, Hilton Head Island
$1,600,000
4 Beds ⋅ 4 Baths ⋅ 4,000 SqFt. ⋅ HILTONHEAD-502113 MLS
Tucked within the coveted Port Royal Plantation and just a short stroll to the Atlantic, this exceptional home invites you to experience coastal living at its most elevated. From the welcoming covered front porch to the grand foyer beyond, every detail is designed to impress while still feeling warm and livable. The expansive living and dining spaces are truly breathtaking, highlighted by soaring 22-foot beamed ceilings, a striking wood-burning fireplace, rich parquet floors, and plantation shutters that bathe the home in soft natural light. At the heart of the home, the gourmet kitchen is both beautiful and functional, featuring a large center island, Monogram gas range, double pantries, granite countertops, elegant tile flooring, and a whole-home water purification system for added peace of mind. Just beyond, the inviting family room is perfect for gathering, complete with a second fireplace, coffered ceilings, and a stylish wet bar. A separate music room or den offers a cozy retreat, while a private office with custom built-ins creates an ideal work-from-home space. The first-floor primary suite is a true sanctuary, offering dual walk-in closets and a spa-like bath with a jetted tub and walk-in shower. Upstairs, three generously sized bedrooms, two full baths, and abundant closet space provide comfort and privacy for family and guests, all connected by a graceful balcony overlook. The home continues to impress with a versatile workshop and laundry area adjoining the two-car garage, finished with carpet-perfect for a hobby space or relaxed lounge. Step outside and enjoy thoughtfully designed outdoor living, including a grilling area, private outdoor shower, and a stunning screened porch with a retractable screen that opens to beautifully manicured gardens. Serene lagoon and golf course views across the 12th and 13th holes create a picturesque backdrop for everyday living. As a resident of Port Royal Plantation, you'll enjoy access to world-class amenities including championship golf, tennis and pickleball, a pool, clubhouses, dining, and more. A rare opportunity to own a home that perfectly blends luxury, comfort, and the timeless charm of the Lowcountry-this is one you won't want to miss. Furniture negotiable.

22 Sovereign Drive, Hilton Head Island

Listing courtesy of Keller Williams Realty. Selling Office: EXP Realty LLC.

4 Pieces Of Eight Place, Hilton Head Island
$1,550,000
4 Beds ⋅ 3 Baths ⋅ 2,815 SqFt. ⋅ HILTONHEAD-508744 MLS
Experience the perfect blend of modern sophistication and relaxed coastal flair in this stunning, move-in-ready single-story home. From the moment you arrive, the tone is set by an understated, winding driveway that guides you through a beautifully shaded tree canopy. Built on a highly desirable, high-elevation lot within an X elevation zone, this home exudes exceptional pride of ownership both inside and out. Step inside to find expansive, sun-lite living spaces defined by soaring vaulted wood ceilings and walls of glass that frame your private paradise. The thoughtfully designed layout effortlessly connects the public living areas, featuring: A Refreshingly modern kitchen anchored by a show-stopping porcelain island.The Great Room: A warm, inviting space complete with beautiful architectural wood ceilings and one of the home's two cozy fireplaces. The layout ensures peace and quiet for both owners and visitors by placing the bedrooms in separate wings. A private primary sanctuary occupies its own side of the home, offering an peaceful retreat.Guest bedrooms on the opposite side of the home, ensuring total comfort and privacy for family or friends. Every bedroom features walls of glass, allowing everyone to wake up to serene garden views.The interior seamlessly transitions to the outdoors, where private, meticulously manicured gardens and grounds unfold. Enjoy stunning, sweeping views of multiple golf course fairways right from your backyard. The property is completed by an expansive 4-car garage, offering abundant storage for vehicles, workshop, hobbies, and beach gear. Located within the exclusive, private beachside community of Port Royal Plantation. Want to see more? Be sure to click the video link to take and explore all the incredible attributes this lovely home and location have to offer.

4 Pieces Of Eight Place, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Berkshire Hathaway HomeServices Hilton Head Bluffton Realty.

3 Craven Place, Hilton Head Island
$1,530,000
3 Beds ⋅ 3 Baths ⋅ 2,438 SqFt. ⋅ HILTONHEAD-507471 MLS
Beautiful ocean-side custom home in Port Royal, fully remodeled in 2018 and in excellent condition. This 3-bedroom, 2.5-bath home offers true single-level living with a 2-car garage, all set on nearly an acre in one of Hilton Head's most sought-after communities. The home features a completely updated kitchen with quartz countertops, stainless steel appliances, and a gas range, along with renovated bathrooms, updated flooring, fresh paint, and vaulted ceilings throughout. The living room offers a brick fireplace and soaring ceilings, creating a bright and inviting space. The spacious layout provides great bedroom separation, including a primary suite with a large walk-in closet, glass-enclosed shower, and double vanities. Enjoy outdoor living with a screened porch and expansive back deck overlooking a serene fairway and lagoon view. Additional highlights include being sold fully furnished-move right in and start enjoying the coastal lifestyle. Just a short walk to the beach! Located in Port Royal, the island's only private oceanfront gated community with no short-term rentals, offering unmatched privacy and tranquility.

3 Craven Place, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Charter One Realty.

6 Princeton Circle, Hilton Head Island
$1,500,000
3 Beds ⋅ 3 Baths ⋅ 2,462 SqFt. ⋅ HILTONHEAD-507815 MLS
Tucked inside the prestigious oceanfront community of Port Royal Plantation, this charming courtyard-style home offers an inviting blend of privacy, space, and coastal convenience-just moments from the beach. Approximately 2,452 square feet, the home welcomes you with a foyer entry that opens into a thoughtfully designed layout. A dining area & spacious living room w/ a cozy corner fireplace create an ideal setting for both everyday living & entertaining, while a wet bar adds a touch of sophistication. The full kitchen features a delightful breakfast nook perfect for casual meals or morning coffee. True to its courtyard design, the main living spaces flow seamlessly to a lovely private paved patio-an intimate outdoor retreat surrounded by mature landscaping and set along a peaceful lagoon, offering beauty and privacy. The home includes 3 bedrooms and 3 full baths, with a desirable separation of space. The primary suite is conveniently located on the main level and features sliding doors that open directly to the serene courtyard. Upstairs, the only room is a private ensuite guest bedroom complete with its own balcony-an ideal haven for visitors. Additional highlights include a dedicated laundry room, a two-car garage, and a layout well-suited for low-maintenance living-perfect as a full-time residence or a "lock-and-leave" getaway. The courtyard style provides charm and gardening opportunities without extensive upkeep. Residents of Port Royal Plantation enjoy an exceptional lifestyle with access to a beachfront community center featuring an expansive deck, screened porch, pool, playground, fire pits, basketball court, and multipurpose rooms. The community also offers tennis and pickleball courts, leisure trails, gardens, and 24-hour security. Optional membership available at Port Royal Golf & Tennis Club. A rare opportunity to own a distinctive home in one of Hilton Head's most sought-after private communities-where coastal living meets comfort and character.

6 Princeton Circle, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Charter One Realty.

12 Coquina Road, Hilton Head Island
$1,475,000
3 Beds ⋅ 4 Baths ⋅ 2,726 SqFt. ⋅ HILTONHEAD-451496 MLS
FIVE rows from the beach in the exclusive, gated Port Royal community. With direct access to the beach path, this custom-built Tom Peeples home offers a quick walk to the wide sandy beach. Thoughtfully designed and built in 2001, this residence features 3 spacious bedrooms plus a versatile office/exercise room, ideal for todays lifestyle. The great room is filled with natural light, highlighted by soaring cathedral ceilings and a cozy fireplace perfect for relaxing or entertaining. The formal dining room offers space for gatherings, while the updated kitchen boasts crisp white cabinetry, stainless steel appliances, and plenty of prep space. The oversized garage provides excellent storage for bikes, beach gear, and has a conditioned large flex space, adding to the homes functionality. Whether you're looking for a peaceful primary residence or a second home to escape to, this property is a rare opportunity to own in one of Hilton Head Islands most prestigious ocean-oriented communities. Enjoy the tranquility of a neighborhood that does not allow short-term rentals, preserving a quiet, residential atmosphere. Plus, take advantage of Port Royals private oceanfront community pool, miles of peaceful paths, and the natural beauty that surrounds you. Dont miss your chance to own a piece of coastal paradise and create lasting memories in Port Royal.

12 Coquina Road, Hilton Head Island

Listing courtesy of Keller Williams Realty. Selling Office: Hilton Head Properties.

3 Oak Creek Drive, Hilton Head Island
$1,325,000
3 Beds ⋅ 4 Baths ⋅ 2,382 SqFt. ⋅ HILTONHEAD-505398 MLS
The good life on MIllers Pond with egrets, herons, ibis, and eagles fishing the brackish tidal waters. The hardwood tree canopy including specimen oaks draped with Spanish moss create a postcard setting for this updated home. Step inside to enjoy the ease of single story living with freshly painted open style gathering areas, including great room, dining area, and casual Carolina space with walls of windows to soak in the view. Upper tier kitchen, abundant with custom cabinetry, countertop workspace, and gracious sized center island with bar seating. Appliances include Thermador range with 6 burner gas cooktop and oven, and French door refrigerator. The inclusion of a second wall oven, beverage cooler, and pantry enhances convenience and efficiency for entertaining. Wide plank wood flooring and brick wall with electric fireplace complete the welcoming atmosphere. One guest suite and the primary en-suite (bath with soaking tub, separate seamless glass shower, double vanities, and water closet) overlook the scenic water view and an ample sized 3rd bedroom with private bath includes a walk-in closet. Refined Low Country living located in private ocean front Port Royal Plantation could be yours. Be sure to check out the professionally produced video in the link to experience a virtual tour of this stunning property!

3 Oak Creek Drive, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Sea Pines Real Estate South Beach.

6 Gunpowder Place, Hilton Head Island
$1,275,000
3 Beds ⋅ 3 Baths ⋅ 2,922 SqFt. ⋅ HILTONHEAD-500736 MLS
Bright, open, and airy. This beautifully maintained Port Royal Plantation home offers single-level living with no steps and a thoughtful layout designed for comfort and convenience. Built in 1999, the home features 2,922 square feet with three bedrooms and two and a half baths. Hardwood floors, smooth painted ceilings, high ceilings, and abundant natural light create an inviting atmosphere throughout. The living and dining rooms are accented by a gas fireplace and wet bar, making the home ideal for entertaining. The spacious primary suite includes a walk-in closet, double vanities, shower, and a jetted tub, with an office just off the suite. A two-car garage and full-sized lot complete the property, which is ideally located near the beach and all of the outstanding amenities Port Royal Plantation has to offer.

6 Gunpowder Place, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Keller Williams Realty.

4 Sally Port Road, Hilton Head Island
$1,250,000
3 Beds ⋅ 3 Baths ⋅ 2,786 SqFt. ⋅ HILTONHEAD-453069 MLS
Completely renovated 2024/2025! Brand new kitchen, bathrooms, flooring, room configuration, solid wood doors, office space added, (2) new tankless water heaters, all new appliances 2024, everything you can think of has been done, and most importantly done to the utmost quality and standard. Crafted and curated with a designer's eye to tie in the color palette together, this home exudes excellence in every detail. The Carolina Room looks over the large and private backyard with ample room for your pool oasis. The open floor plan radiates both luxury and comfort an ideal blend for both hosting and relaxation. Walk to the beach, tennis/pickleball courts, golf courses, clubhouse, the amenities of Port Royal right at your fingertips. A must see!

4 Sally Port Road, Hilton Head Island

Listing courtesy of Hilton Head Properties. Selling Office: REsides, Inc..

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