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$5,995,000
6 Beds ⋅ 5 Baths ⋅ 8,000 SqFt. ⋅ HILTONHEAD-502780 MLS
A rare Lowcountry treasure, this exceptional 13+ acre estate spans sweeping marsh and May River frontage and features one of the largest residential docks on the river, at an impressive 150 linear feet. Recently reimagined with a remarkable transformation, this grand property offers a level of scale, privacy, and craftsmanship that truly must be experienced in person. Inside, the main level hosts five spacious bedrooms and four redesigned bathrooms, all thoughtfully designed for effortless single level living. The kitchen has been expanded greatly and flows effortlessly into the expansive great room while an additional poolside living space provides a favored riverfront place of respite. Upstairs, a fully appointed apartment wrapped in rich heart pine paneling provides additional living space with endless views that stretch across the tidal waters. Everywhere you turn, the landscape steals the show. With its unmatched acreage, expansive waterfront, and extraordinary dock, the potential to shape a legacy property for generations to come is unmistakable. This is Lowcountry living at its most timeless, gracious, and unforgettable.

45 Linden Park E Drive, Bluffton

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

$5,990,000
HILTONHEAD-503694 MLS
A rare and breathtaking offering, this 460-acre private island retreat delivers unrivaled seclusion, natural beauty, and timeless luxury-accessible by water only for the ultimate escape. Surrounded by expansive waterways and unspoiled marsh vistas, the island features a beautifully appointed 3-bedroom residence with 4.5 baths, designed for comfort and effortless indoor-outdoor living. A sparkling pool invites relaxation beneath open skies, while equestrian stables add a distinctive touch of sporting elegance and possibility. The deep-water dock accommodates large vessels, providing easy access for boating, fishing, and exploring surrounding waters. Towering trees, open fields, and pristine shoreline create a sense of boundless tranquility and privacy rarely found. Whether envisioned as a legacy family compound, sporting paradise, or exclusive retreat, this extraordinary island offers a once-in-a-lifetime opportunity to own a truly majestic and irreplaceable sanctuary where nature, privacy, and refined living exist in perfect harmony.

Rose Island, Port Royal

Listing courtesy of Collins Group Realty.

$5,900,000
7 Beds ⋅ 8 Baths ⋅ 5,203 SqFt. ⋅ HILTONHEAD-511606 MLS
Properties of this caliber are increasingly difficult to find in Sea Pines. 7 Bedroom/6.5 Baths PLUS Pool Bath, 2022 construction, designer furnished and just a 3-minute walk to the beach. Set on an oversized nearly 1/3-acre 3rd row homesite, this is the rare combination discerning buyers wait years to find. Custom construction and incredibly designed for effortless coastal living, the home showcases sophisticated finishes, soaring ceilings, a gourmet kitchen with a separate prep kitchen, and seamless indoor-outdoor living centered around a covered porch with an outdoor fireplace, summer kitchen, heated pool, and spa. Seven beautifully appointed bedrooms-including a first-floor primary suite and four ensuite guest suites-provide exceptional comfort and privacy, while multiple gathering spaces make the home ideal for entertaining family and friends. Combining exceptional quality, an oversized homesite, beach proximity, and one of Sea Pines' most desirable locations, this is a true legacy property offering the very best of coastal living. Current rental projections of approximately $349,000 annually.

10 Bald Eagle Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

$5,500,000
5 Beds ⋅ 7 Baths ⋅ 7,051 SqFt. ⋅ HILTONHEAD-511760 MLS
BREATHTAKING Mediterranean Estate Home overlooking the 16th Fairway of the Robert Trent Jones Golf Course in Palmetto Dunes. Gated community and just a Short Walk to the Beach. 7,051 Square Feet with Amazing Craftsmanship rarely seen that captivates you. Two-Story Entry with a Grand Marble Staircase, Beautiful Lighting and Travertine Floored Foyer. Inviting Spacious Living Area with a Fireplace and Spectacular Chandeliers overlooks the Large Porch, Patio and Pool Area. Off Living Area is a beautiful Dining Area. A Chef's Dream Kitchen is nearby with a 10-Foot Island that seats 6 plus has a Dining Table. Also, a Comfortable Living Area with a Fireplace that opens to a Veranda with Built in Grilling Area and has Half Bath by Pool. Off Kitchen is a Butler's Pantry and a Laundry Area. Spectacular Wood Paneled Parlor with Sitting Area and Full Bar. 5 Bedroom Suites with Great Separation and Privacy. Primary Bedroom Suite is First Floor, has a Veranda and is steps away to the Raised Invisible Edge Pool and Spa. Also, 2 other Bedrooms have a Veranda. 6-Car Drive Through Cooled Garage, ELEVATOR, Terra Cotta Tile Roof, Paver Driveway and Mature Landscaping. Perfect Home for Relaxing and Entertaining Family, Friends, or Business Outings. Truly EXCEPTIONAL in every way. Come Enjoy the BEST OF LIFE at 11 Sea Lane on Hilton Head Island!

11 Sea Lane, Hilton Head Island

Listing courtesy of Dunes Real Estate.

$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.

$5,499,800
5 Beds ⋅ 5 Baths ⋅ 4,563 SqFt. ⋅ HILTONHEAD-508634 MLS
Designed for those who love to entertain with purpose and elegance, this custom-built seaside home on a rare 0.77-acre lot offers an unmatched relaxed lifestyle both inside and out. Purposely designed by philanthropic owners, the home's open layout including dual sided fireplace effortlessly accommodates private gatherings and charitable galas for 50+ seated guests-flowing smoothly from indoor living spaces to the expansive, light-filled rear veranda. At the heart of the home, a chef's kitchen features a custom wenge wood-top island flanked by durable finished upper tier cabinetry and a massive butler's pantry built to handle full-service catering or intimate family dinners with equal ease. The outdoor sanctuary continues the theme of year-round hospitality, featuring a screened porch with a cozy fireplace, a custom boardwalk, and a climate-controlled heated and chilled pool for seasonal comfort. Two primary ensuites-conveniently situated on both the main and second levels-provide ultimate privacy and flexibility for hosting overnight guests or multi-generational family living. From grand philanthropic events beneath the veranda to quiet mornings on the shoreline, this home embodies the very best of Port Royal coastal living. Click the video link to view interior and drone exterior footage.

3 Wagener Place, Hilton Head Island

Listing courtesy of Charter One Realty.

$5,295,000
5 Beds ⋅ 6 Baths ⋅ 4,965 SqFt. ⋅ HILTONHEAD-503477 MLS
A rare opportunity, nestled on over 2 acres in popular Sea Pines. This Lowcountry, custom estate features a private, detached multi-purpose cottage, quietly located in the rear of the property, accessed exclusively by a land bridge. A beautifully curated 5 bedroom compound, set among majestic live oaks and pines, offers a sanctuary with single level living on the main floor, a private lagoon, pool/spa along with multiple outdoor spaces, ideal for entertaining. Throughout the main living areas you'll find rich hardwood floors, beautiful trim details and walls finished in sophisticated, classic neutral tones-creamy whites and warm taupes. The kitchen sets the tone of the home with natural dolomite countertops, taupe perimeter and island cabinets with custom arched oak upper cabinets flanking the range, complete with pure brass hardware. The mix of traditional selections is balanced with a modern, linear light fixture over the island. The scullery kitchen provides ample prep space and storage in addition to a dedicated pantry. Enjoy mixing cocktails in the well appointed wet bar with floating shelves and knurled brass plumbing. Features in the bathrooms include timeless marble mosaics paired effortlessly with curated ceramics complete with custom cabinetry and classic hardware selections. This commitment to mixing the traditional with modern, high-end selections guarantees a home that will never go out of style. Experience working remotely in the study featuring custom built-in desks. Dramatic, cathedral ceilings make the home feel larger than life. A media room invites you to relax and linger. Details abound with ceilings trimmed in tongue and groove, shiplap walls, custom wood stained wall paneling, arched built-ins, custom built-in office. The versatile guest cottage welcomes friends and family, featuring a living room, wet bar, bedroom, full bathroom, and additional garage space for up to three vehicles. An expansive screened porch enhances the outdoor experience, making it perfect for gatherings such as oyster roasts or bourbon tastings, or simply relaxing while enjoying the picturesque natural surroundings. Experience a home that seamlessly integrates classic design with modern living amidst the scenic beauty rooted in Lowcountry heritage.This property offers a unique experience of residing on a secluded estate with world-class amenities including golf, tennis, stables, a nature preserve, restaurants and shops just a stroll away.

4 Plantation Drive, Hilton Head Island

Listing courtesy of Howard Hanna Allen Tate Lowcountry.

$5,250,000
4 Beds ⋅ 5 Baths ⋅ 5,079 SqFt. ⋅ HILTONHEAD-501241 MLS
Escape to Ridgeland Ranch, a breathtaking 26.36-acre equestrian estate where Lowcountry elegance meets world-class horse facilities. Inspired by the timeless sophistication of Palmetto Bluff, this private sanctuary offers the perfect blend of luxury living and equestrian excellence.The custom-built Lowcountry home, crafted by renowned builder Mike Tuten, showcases exquisite attention to detail with reclaimed materials throughout. Soaring vaulted ceilings with exposed beams frame the magnificent brick fireplace, while hickory floors and custom millwork create an atmosphere of refined warmth. The gourmet kitchen features polished black granite countertops, a Sub-Zero refrigerator, and a stunning six-oven AGA range in navy blue.The crown jewel is the state-of-the-art Morton Barn with its impressive 200' x 100' covered arena, complete with professional footing, LED lighting, and sound system. Eight custom 12' x 12' stalls, climate-controlled tack and feed rooms, and a luxurious 2-bedroom apartment above provide everything the serious equestrian demands.Entertainment abounds with an infinity-edge pool cascading into the private pond, a recreation suite featuring a bar, pool table, and authentic Boston firehouse pole, plus a newly resurfaced pickleball court and outdoor kitchen. The handmade brick courtyard with fire pit offers the perfect gathering space.Located minutes from I-95, Ridgeland Ranch provides unparalleled access to major equestrian circuits including Wellington, Ocala, Tryon, Aiken, and Lexington, while offering the privacy and natural beauty near the acclaimed ACE Basin. This is more than a propertyit's a lifestyle, a legacy, and a dream realized.

165 Golda Drive, Ridgeland

Listing courtesy of Maxey Blackstream Christie's International Real Estate.

$5,195,000
6 Beds ⋅ 7 Baths ⋅ 4,147 SqFt. ⋅ HILTONHEAD-506680 MLS
Experience the perfect blend of luxury, comfort, and investment potential in this exceptional **direct oceanfront** retreat on Singleton Beach. Offering the rare opportunity to own a beachfront home in one of Hilton Head Island's most desirable locations, this property is designed for both personal enjoyment and vacation rental success.Thoughtfully designed with spacious living areas, the home features an open-concept floor plan filled with natural light, ideal for entertaining or relaxing after a day on the beach. The well-appointed kitchen flows seamlessly into the main living space, while multiple bedrooms provide comfort and privacy for owners and guests alike. Inviting outdoor living spaces offer the perfect setting to unwind, dine, and enjoy the sights and sounds of the Atlantic Ocean.The property has a proven rental history and strong income potential. Current ownership has taken a more selective approach to rentals, prioritizing personal use and minimizing wear and tear, creating an opportunity for a future owner to optimize the rental program based on their goals.Recent improvements include three new HVAC systems, with one replaced in 2024 and two replaced in 2025, providing added efficiency, reliability, and comfort throughout the home.Whether you're seeking a private beachfront retreat, a second home, or an investment property, this direct oceanfront residence offers an exceptional combination of location, condition, and rental potential on Singleton Beach.

19 Singleton Beach Place, Hilton Head Island

Listing courtesy of Palmetto Coast Realty Group.

$5,099,000
5 Beds ⋅ 6 Baths ⋅ 3,625 SqFt. ⋅ HILTONHEAD-503980 MLS
Experience the pinnacle of oceanfront living on Hilton Head Island in this fully turnkey beach home with unobstructed Atlantic Ocean views. Located on one of the island's most desirable beaches, this oceanfront property for sale offers stunning eastern exposure with unforgettable sunrises, expansive shoreline views, and the calming sound of waves crashing on the shore. Meticulously maintained and never rented, the home features a new chef's kitchen, five bedrooms with ensuite bathrooms, including multiple oceanfront primary suites with private balconies overlooking the water. Enjoy a private oceanfront pool with an elevated deck designed to maximize beach and ocean views, plus a new private boardwalk that's a hop, skip, and jump to toes-in-the-sand. Use as a primary residence, second home, or high-end Hilton Head vacation rental, either way, the memories you'll make inside, outside, on the beach, and anywhere else on America's #1 Island are priceless, while the potential for high rental income production and future appreciation makes this a smart investment. Oceanfront homes on Hilton Head Island priced this low are a rarity, making this luxury oceanfront residence a truly exceptional opportunity. If you're going to buy oceanfront, do it like this! Now is the time to make your dreams a reality!

16 Whelk Street, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$5,000,000
8 Beds ⋅ 8 Baths ⋅ 4,510 SqFt. ⋅ HILTONHEAD-504438 MLS
Wake up to the sound of waves at this exceptional oceanfront estate in coveted Forest Beach. This 8-bedroom, 7.5-bathroom retreat isn't just a home-it's a gateway to the Hilton Head lifestyle you've been dreaming of. Step inside to sun-drenched living spaces where floor-to-ceiling windows frame unobstructed ocean views like living artwork. The open-concept design flows effortlessly from room to room, perfect for gatherings large and intimate. Contemporary finishes meet coastal charm throughout, creating spaces that feel both sophisticated and refreshingly relaxed. Outside, your private dune landscape provides direct beach access-no streets to cross, no long walks. Just steps from your door to your toes in the sand. Whether you're hosting extended family, running a successful vacation rental, or simply claiming your piece of paradise, this property delivers the rare combination of luxury, location, and lifestyle. With 8 generously sized bedrooms, there's room for everyone to spread out and create their own coastal memories. The 7.5 bathrooms ensure comfort and convenience, while the distinctive architectural style sets this property apart from typical beach homes.Forest Beach location. Oceanfront position. Unmatched potential. Your next chapter starts here.

7 Guscio Way, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$4,995,000
5 Beds ⋅ 5 Baths ⋅ 5,009 SqFt. ⋅ HILTONHEAD-505600 MLS
174 Hunting Lodge Road is a five-bedroom, four-and-a-half bathroom coastal Lowcountry-style home and carriage house in the River Road neighborhood of Palmetto Bluff. Taking full advantage of its .66 acres, the home spreads along a sweeping stretch of inland waterway shoreline in the rear. Built by Shoreline Construction from a Court Atkins Group design, this home's design emphasizes a breezy flow from space to space within its 5,009 square feet, informed by a comfortable sense of grandeur. Complementing this spacious atmosphere are elegant textures and materials from the reclaimed flooring of the great room to the designer lighting found throughout. This scale and beauty is established the moment you pull into the wide circular driveway, with soaring metal rooflines cascading down to a wraparound front porch. Inside, the great room opens from there, with wood flooring contrasting with rich creamy tones on a coffered ceiling as well as built-ins that flank the gas fireplace. That sense of flow breezes into the expansive kitchen boasting craftsman cabinets, gas range and pendant lighting, centered on a wide marbled center island. For easy entertaining, a passage to one end opens to the back kitchen's plentiful storage, wine cooler and prep space, with a full laundry just beyond. Formal dining at the other end of the kitchen sits at the center of panoramic views out to the water through the screened porch. Accessed through doors at either side of the dining room, or via wide sliders from the great room, this year-round retreat spans the rear of the property with space for al fresco dining or outdoor entertaining by the fireplace and grilling porch. The primary suite enjoys the best of all this home has to offer, with rich finishes, elegant spaciousness and water views. Set off a private hallway, it boasts dual walk-in closets and a massive ensuite bath with walk-in shower, garden tub and dual-basin vanity. Guest quarters spread throughout the property for lush privacy. The first is the carriage house set above the two-car garage with golf cart port, offering a private bath and spacious lounge. Three more bedrooms share the main house's second-floor lounge and upper porch. A full suite upstairs enjoys a spacious closet and ensuite bath, while a further two bedrooms each share a private bath with dual-basin vanity. In one, waterfront views from an integrated bed steal the show. In the other, custom-crafted bunks create a relaxed atmosphere of fun.

174 Hunting Lodge Road, Bluffton

Listing courtesy of Palmetto Bluff Real Estate Co.

$4,800,000
HILTONHEAD-448902 MLS
59 unit apartments. Perfect for a nursing facility, surgical recovery facility, lower income housing, weight loss facility, etc...

800 Fording Island Road, Bluffton

Listing courtesy of Realty One Group - Lowcountry.

$4,750,000
4 Beds ⋅ 5 Baths ⋅ 2,216 SqFt. ⋅ HILTONHEAD-500657 MLS
Incredible development opportunity on Hilton Head Island with the potential for 8 UNITS AN ACRE, featuring marsh and sound views with a designated beach walk easement. Four combined parcels span over four acres, offering rare potential for a private estate, multi-home enclave or workforce housing. The property adjoins historic Mitchellville Freedom Park, providing a unique setting rich in natural beauty and heritage. A gracious 2200 SF home with additional SF in separate barn and apartment (6000+ total finished SF on the property) already on-site can serve as a primary residence, creating a sprawling private compound, or function as a clubhouse for future residences. Whether envisioned as a legacy property or an investment in a premier coastal destination, this offering presents unmatched possibilities in one of Hilton Heads most desirable locations.

170 Dillon Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

$4,600,000
4 Beds ⋅ 6 Baths ⋅ 6,042 SqFt. ⋅ HILTONHEAD-447864 MLS
This one-of-a-kind property is privately sited on almost an acre lot with panoramic marsh and water views providing the perfect backdrop for spectacular sunsets. Kermit Huggins, renowned architect, designed this property with 2 structures that harmoniously co-exist with their natural surroundings. Special features include new metal roof, hardwood flooring, pella windows/doors, renovated kitchen,& interior paint. The main house boasts an upper level luxurious owner suite & guest house has 2 en-suite bedrooms plus kitchenette. Incredible outdoor living with heated/chilled saltwater pool, expansive deck, and private dock. Waterfront Perfection!

29 Baynard Park Road, Hilton Head Island

Listing courtesy of Charter One Realty.

$4,500,000
HILTONHEAD-502697 MLS
Introducing a rare opportunity to own approximately 304 acres of prime land ideally located just off Interstate 95 at the Cossawhatchie (Exit 28) interchange in Jasper County, South Carolina. These two adjoining parcels, 060-00-05-065 and 060-00-05-064, offer an exceptional location with direct interstate access, high visibility, and unlimited potential for future development. Perfectly positioned between Savannah and Charleston, this property sits in the path of regional growth and is ideal for a wide range of commercial, industrial, or mixed-use ventures. With its expansive acreage and immediate access to I-95, the site presents a blank canvas for visionary investors or developers seeking to capitalize on one of the Southeast's busiest transportation corridors. Imagine transforming this tract into a major travel plaza or truck stop, serving thousands of daily commuters and freight haulers that move up and down the East Coast. Alternatively, the land could easily support a logistics hub, warehouse complex, or distribution center, taking full advantage of the site's connectivity to regional ports and highway systems. For those thinking long term, the acreage lends itself to a mixed-use commercial development blending retail pads, lodging, dining, or even an RV park - creating a true gateway destination for travelers and the local community alike. This property combines size, location, and accessibility in one exceptional package - a strategic investment for those looking to secure land with both immediate and future potential. With over 300 acres of opportunity, direct frontage near I-95, and the freedom to bring your vision to life, this Cossawhatchie tract stands ready to become the next landmark destination along South Carolina's thriving Lowcountry corridor.

Morgandollar Road, Ridgeland

Listing courtesy of Maxey Blackstream Christie's International Real Estate.

$4,499,000
7 Beds ⋅ 9 Baths ⋅ 4,440 SqFt. ⋅ HILTONHEAD-507459 MLS
Exceptional second-row ocean-oriented home in North Forest Beach, just moments from the sand via a short beach path and conveniently located near Coligny Plaza. Built in 2021, this stunning coastal retreat offers 7 bedrooms, 7 full baths, and 2 half baths across 4,440 square feet of thoughtfully designed living space.Featuring soaring ceilings and an open-concept layout, the home is designed for both luxury living and entertaining. The chef's kitchen is a standout with double islands, high-end finishes, and ample space for gathering. An elevator provides easy access to all levels, while multiple living areas-including two tranquil screened porches-offer seamless indoor-outdoor living.Step outside to a private backyard oasis complete with a heated pool and spa, perfect for relaxing after a day at the beach. Situated on a desirable corner lot at the quiet end of Dune Lane, the property offers ample private parking and added privacy.Sold fully furnished and golf cart friendly, this home is not only a beautiful coastal getaway but also a proven, lucrative investment opportunity in one of Hilton Head Island's most sought-after rental locations.

134 Dune Lane, Hilton Head Island

Listing courtesy of Schembra Real Estate Group.

$4,495,000
4 Beds ⋅ 5 Baths ⋅ 4,616 SqFt. ⋅ HILTONHEAD-511638 MLS
A remarkable expression of Lowcountry luxury, this exceptional custom residence is perfectly positioned on a quiet cul-de-sac in the prestigious Port Royal community, offering the rare opportunity to enjoy both breathtaking marsh front living and easy access to the beach. Here, you don't have to choose between sweeping tidal marsh views and walking distance to the beach, this home offers both. Encompassing more than 4,600 square feet of thoughtfully designed single-level living, the home captures panoramic vistas of Fish Haul Creek, the tidal marsh, and the Atlantic Ocean beyond while blending timeless architecture with impeccable craftsmanship. From the impressive front elevation and grand wrought-iron staircase to the custom wood and glass entry doors, every detail has been carefully curated. Inside, soaring ceilings, custom millwork, coquina-shell columns, extensive stone flooring, designer lighting, walls of glass, and multiple fireplaces create warm yet sophisticated living spaces designed to showcase the surrounding natural beauty. The gourmet kitchen is a chef's dream, featuring premium Wolf, Viking, Bosch, and Sub-Zero appliances, custom cabinetry, generous prep space, and an adjoining butler's pantry with wet bar-ideal for entertaining. The luxurious primary suite serves as a private retreat with veranda access, custom walk-in closets, and a spa-inspired bath complete with heated stone floors, a soaking tub, oversized walk-in shower, and skylight. Two additional guest suites, a dedicated office, elevator access, and a spacious six-car climate-controlled garage provide exceptional flexibility for family and guests alike. Designed for year-round enjoyment, the outdoor living spaces are equally impressive. Expansive covered verandas, exposed cypress beams, an outdoor fireplace, built-in grilling area, professionally designed gardens, a custom hot tub with waterfall, and a private dock with a floating dock on Fish Haul Creek create an extraordinary setting for entertaining or simply enjoying the peaceful waterfront surroundings. Whether you're launching a kayak from your backyard, spending the afternoon on the beach just moments away, or watching spectacular sunsets over the marsh from your veranda, this one-of-a-kind estate offers an unparalleled coastal lifestyle in one of Hilton Head Island's most coveted communities.

127 Fort Walker Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

$4,495,000
6 Beds ⋅ 7 Baths ⋅ 3,702 SqFt. ⋅ HILTONHEAD-510711 MLS
LOVE AT FIRST SIGHT! Welcome to 5 Junket, a stunning coastal estate nestled on a premier second-row homesite in one of the most coveted locations within Palmetto Dunes, where timeless coastal elegance, modern luxury, and extraordinary beach access come together to create a home families treasure for generations. Rarely does a property capture everything buyers envision when they dream of owning on Hilton Head Island. Just steps from the beach and beautifully reimagined from top to bottom, this is a home where mornings begin with a walk on the sand, afternoons unfold around the pool, and family and friends gather year after year to create memories that last a lifetime. Offering six bedrooms, six-and-a-half baths, expansive indoor and outdoor living spaces, and extensive recent renovations, the home lives as comfortably as it entertains. Whether enjoyed as a full-time residence, a cherished second home shared with family and friends, or a luxury beach retreat with an exceptional rental history, 5 Junket delivers a lifestyle that has become increasingly difficult to find and nearly impossible to recreate.

5 Junket, Hilton Head Island

Listing courtesy of Harbour & Home Real Estate.

$4,495,000
4 Beds ⋅ 5 Baths ⋅ 4,074 SqFt. ⋅ HILTONHEAD-510566 MLS
Truly an iconic landmark residence along the shores of the Port Royal Sound on Hilton Head Island, this exceptional coastal offering captures the essence of luxury in the Lowcountry. Designed by one of Hilton Head's most notable architects, the home features four spacious bedrooms, each with en suite baths, along with sweeping sunrise vistas across the Sound from every room within. The open and thoughtfully designed floor plan now includes a newly expanded and reimagined ground-floor owner's suite. This private retreat with effortless main-level living is in immaculate turn-key condition, including the newly redesigned pool and spa. The gourmet kitchen is appointed to satisfy the most discerning chef, while poolside dining beneath the screened lanai promises year-round alfresco entertaining. The nearby Hickory Forest beachwalk offers direct access to the natural beach and is sure to become a cherished destination for the future owner of 6 Herring Gull.

6 Herring Gull Lane, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

$4,495,000
5 Beds ⋅ 6 Baths ⋅ 3,662 SqFt. ⋅ HILTONHEAD-446499 MLS
This new, five-bedroom, five-and-one-half-bath cottage by Palmetto Bluff Builders is in the Montage Residences neighborhood across the street from Montage Palmetto Bluff. Newly finished, this cottage maximizes its single story design with multiple indoor & outdoor living spaces & a detached carriage house. Exterior detailing, such as louvered shutters, tabby stucco and brick detail, and a metal roof add timeless appeal. As part of the Montage Residences, homeowners enjoy the signature amenities of Montage Hotels & Resorts with dedicated staff. This cottage has easy access to RT’s Market, Wilson Lawn & Racquet Club, and Wilson Landing.

130 August Lane, Bluffton

Listing courtesy of Palmetto Bluff Real Estate Co.

$4,375,000
6 Beds ⋅ 7 Baths ⋅ 7,636 SqFt. ⋅ HILTONHEAD-507884 MLS
Nestled on over three acres of beautifully wooded waterfront land overlooking scenic marshes out to the Colleton River, this magnificent Victorian-style estate features, more than 8,000 square feet of timeless elegance and careful craftsmanship. From the moment you arrive, the thoughtfully landscaped graceful central courtyard welcomes you. Surrounded by mature trees, and the tranquil sounds of nature, this property offers rare privacy and the best of refined Southern living - a special opportunity to own a grand waterfront estate where history, craftsmanship, and natural beauty meet.The primary residence with its unobstructed and protected view boasts stately architecture, intricate millwork, hand hewn oak flooring and the warmth of exquisite paneling throughout. The spacious formal and casual living areas blend historic charm with modern comfort. The chef's kitchen has a practical and purposeful attached secondary prep room. Specialty lighting and fixtures and imported tiles throughout. Large windows and inviting verandas frame sweeping views of the river and surrounding marshes, creating a sense of serenity in every room. The expansive second-floor covered deck provides the perfect vantage point for relaxing with morning coffee. The two upstairs bedrooms feature individual bathrooms and dressing spaces. A shared tidal dock with private float offers direct access for boating, kayaking, fishing, crabbing or simply enjoying the natural beauty of the Low Country waterfront. The second dwelling on the estate features three-bedrooms, three ensuite baths, a complete full kitchen, and a lovely veranda, providing family and guests with a private retreat that mirrors the charm and quality of the main residence. The second floor bedroom is complete with two sets of built in bunk beds and a large living area. Additionally, the property has a studio building which features a two-car garage with a spacious flex space offering endless possibilities with its convenient full bath and kitchenette.

25 Goose Pond Circle, Okatie

Listing courtesy of Spring Island Realty LLC.

$4,350,000
5 Beds ⋅ 6 Baths ⋅ 4,702 SqFt. ⋅ HILTONHEAD-511693 MLS
Set on a beautifully positioned half-acre homesite, 24 Butterweed Road is a 4,702-square-foot home offering five bedrooms, five full baths, and one half bath across a thoughtfully designed main residence and private carriage house. Designed by acclaimed architect Court Atkins, built by CS Thomas Construction, and thoughtfully landscaped by Witmer Jones Keefer, this home embodies the timeless character and effortless livability that define Palmetto Bluff. Warm, welcoming, and exceptionally functional, the home is centered around expansive gathering spaces with hand crafted plaster walls where the kitchen, dining area, and great room flow seamlessly to a screened porch designed for effortless entertaining. Anchored by a fully equipped outdoor kitchen featuring both a built-in grill and an open fire Argentinian grill, this inviting space overlooks a private courtyard where a natural wood pizza oven and central fire pit creates a natural gathering place for evenings spent with family and friends beneath the Lowcountry sky. Just beyond the beautifully appointed kitchen, a well-equipped back kitchen enhances everyday living while concealing meal preparation from the main entertaining spaces. Adjacent to this service area, a temperature-controlled wine cellar offers the perfect setting to curate and display a treasured collection, bringing both function and sophistication to the heart of the home. The first-floor primary suite serves as a peaceful retreat, complemented by an additional guest suite on the main level. Upstairs, a spacious guest bedroom, comfortable lounge, and charming bunk room create an inviting haven for family and visitors, offering flexible accommodations that encourage extended stays and memorable gatherings. Above the detached two-car garage, a private office serves as a dedicated workspace, offering exceptional flexibility for remote work, creative pursuits, or future adaptation to suit a variety of lifestyle needs. Every detail reflects a thoughtful balance of refined craftsmanship and relaxed comfort, where generous porches, curated outdoor spaces, and seamless indoor-outdoor connections invite a lifestyle centered on gathering, entertaining, and enjoying the natural beauty that surrounds the home.

24 Butterweed Road, Bluffton

Listing courtesy of Palmetto Bluff Real Estate Co.

$4,350,000
5 Beds ⋅ 6 Baths ⋅ 4,100 SqFt. ⋅ HILTONHEAD-503345 MLS
Located in the highly sought-after North Forest Beach neighborhood of Hilton Head Island, 3 Driftwood Lane is a rare coastal luxury home situated on a private street of just nine residences that share exclusive private beach access reserved solely for the street. This spacious five-bedroom home with four full and two half bathrooms offers approximately 4,100 square feet of living space, combining privacy, close proximity to the beach, and refined Lowcountry design. Designed for elevated coastal living, the property features a resort-style outdoor living area with an elevated pool and spa, an outdoor kitchen, and a private outdoor shower and bathroom, making it ideal for seamless indoor-outdoor entertaining. Interior living spaces are generously sized and provide flexible accommodations for family and guests, while the oversized garage offers abundant storage, a valuable feature for beach gear and everyday convenience.Just steps from the Atlantic Ocean and minutes from Hilton Head Island's premier shopping, dining, and entertainment, this North Forest Beach home offers an exceptional blend of seclusion and accessibility. Whether used as a primary residence, a luxury second home, or a high-end vacation rental investment, 3 Driftwood Lane represents a rare opportunity to own a private beach access home in one of Hilton Head's most desirable locations.

3 Driftwood Lane, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$4,300,000
4 Beds ⋅ 5 Baths ⋅ 7,324 SqFt. ⋅ HILTONHEAD-509253 MLS
Custom waterfront estate in the prestigious gated community of Windmill Harbour, home of the South Carolina Yacht Club, offering an exceptional Lowcountry boating lifestyle. Situated on 2 harbor-front lots with 2 private 70' boat slips, this custom residence was designed for luxury living and entertaining. Expansive open spaces, soaring ceilings, fireplaces, and multiple balconies capture stunning water views throughout. The main level features the primary suite, private office, formal dining room, spacious living areas, and a chef's kitchen with premium appliances. The 4th bedroom above the 3-car garage offers flexible use as a guest suite, media room, exercise space, or mother-in-law suite. Room for a custom pool and outdoor kitchen. Convenient to Bluffton, Savannah, golf, dining, and beaches.

34 Sparwheel Lane, Hilton Head Island

Listing courtesy of Collins Group Realty.

$4,300,000
6 Beds ⋅ 7 Baths ⋅ 7,320 SqFt. ⋅ HILTONHEAD-453824 MLS
Your Dream Awaits with a 4-minute walk to the beach, inside this stunning, renovated, luxury masterpiece nestled in an exclusive beachside gated community. This Goliath-sized, breathtaking home is a place to live, a lifestyle, and a lucrative STR investment. Enjoy a very short walk to the beach, one of your many private terraces overlooking your private heated pool or the golf course, and evenings spent entertaining in exquisite designer spaces. Modern amenities, Expansive floor plan, peaceful, private & gated, & a proven rental revenue stream. Your chance has arrived to own a slice of heaven that could pay for itself. Community/home video available.

12 Port Tack, Hilton Head Island

Listing courtesy of EXP Realty LLC.

$4,250,000
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.

$4,250,000
6 Beds ⋅ 6 Baths ⋅ 6,000 SqFt. ⋅ HILTONHEAD-450230 MLS
Stunning deep-water residence in Sea Pines features a private, oversized dock with a boat lift, offering unparalleled waterfront access. Spanning nearly 6,000 square feet, the open floor plan showcases breathtaking, unobstructed water views. The entertainer’s dream kitchen boasts a 60” Viking gas range, double stainless steel refrigerator, walk-in pantry, and a striking 12-foot granite bar complete with a wine cooler and ice maker. The outdoor living space features a circular driveway with pervious pavers, a resort-style private pool and hot tub, and a fire pit—all set within over 3,000 square feet of beautifully designed patio space. OSCREA

25 N Calibogue Cay Road, Hilton Head Island

Listing courtesy of DOT REAL ESTATE.

$4,200,000
4 Beds ⋅ 4 Baths ⋅ 2,918 SqFt. ⋅ HILTONHEAD-504969 MLS
This exceptional second-row ocean home in Sea Pines offers a compelling blend of location, scale, and long-term flexibility. Just steps to the beach, expansive first- and second-level balconies capture ocean views and coastal breezes, while a private pool creates an ideal setting for outdoor living and entertaining. Inside, nearly 3,000 square feet of light-filled living space showcases an open-concept design with oversized windows and skylights. The thoughtfully designed floor plan includes 4 bedrooms plus a bunk room and 3.5 baths, providing flexible accommodations for family, guests, or rental demand. The first level features a secondary primary suite, while additional bedrooms are connected by a Jack and Jill bath, creating functional and private guest spaces. Upstairs, the primary suite serves as a quiet retreat. A fully equipped kitchen, garage parking, washer and dryer, gas grill, and electric vehicle charger enhance everyday functionality. Enjoy easy access to the beach and a short walk to South Beach Marina, offering premier tennis and pickleball facilities, or relax and dine at the iconic The Salty Dog Cafe. Whether positioned as a legacy coastal retreat or a high-performing investment property, this home represents a rare opportunity in one of Hilton Head Island's most desirable ocean-oriented communities.

1 Brown Pelican Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate South Beach.

$4,195,000
5 Beds ⋅ 6 Baths ⋅ 3,828 SqFt. ⋅ HILTONHEAD-511419 MLS
Gracefully positioned on a half-acre homesite overlooking one of River Road's picturesque neighborhood parks, 159 Red Ochre Road is a timeless Lowcountry retreat where thoughtful architecture, exceptional craftsmanship, and an unparalleled setting come together. Designed by Residential Concepts Design Group, built by JParker Homes in 2023, and complemented by the landscape architecture of Lowcountry Tide Design, the residence embraces the beauty of its surroundings with inviting porches, generous living spaces, and a seamless connection to the outdoors. Offering 3,828 heated square feet, the home features five bedrooms, four full baths, and one half bath thoughtfully arranged to provide both privacy and flexibility. The main residence centers around an expansive great room and chef's kitchen that flow effortlessly to a screened porch, creating ideal spaces for entertaining or relaxed everyday living. A private first-floor primary suite offers a peaceful retreat, while two guest bedrooms, an upper-level loft and study, and a spacious bonus bunk room above the garage provide comfortable accommodations for family and guests alike. A detached guest cottage with its own living room, loft, and private entrance creates an inviting space for extended family, visiting friends, or multigenerational living, ensuring every guest enjoys both independence and connection. Just beyond the front door, the home's exceptional location enhances the Palmetto Bluff lifestyle. The adjacent neighborhood park serves as an extension of the property, while a scenic walking path winds through the greenspace to a shared community dock, inviting mornings on the water, afternoon kayak excursions, or quiet evenings taking in the beauty of the surrounding Lowcountry landscape. Located within River Road, one of Palmetto Bluff's most sought-after neighborhoods, residents enjoy immediate access to miles of nature trails, parks, inland waterways, and the community's celebrated collection of dining, golf, recreation, and wellness amenities. Blending timeless design with modern comfort in an extraordinary setting, 159 Red Ochre Road presents a rare opportunity to experience the very best of life at Palmetto Bluff.

159 Red Ochre Road, Bluffton

Listing courtesy of Palmetto Bluff Real Estate Co.

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