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$2,490,000
3 Beds 4 Baths HILTONHEAD-507275 MLS
Harbourfront elegance in Windmill Harbour. Positioned on two lots in one of Hilton Head Island's most exclusive private communities, 1 Sailwing Lane is a residence of uncommon quality, privacy, and architectural distinction. Designed with true flair, the home captures the beauty of its harbourfront setting while offering a warm, sophisticated interior made for both everyday living and gracious entertaining.The gourmet kitchen anchors the home with style and function, while the primary suite is a retreat of its own-complete with a fireplace and a spa-inspired bath featuring a large soaking tub. An open den/loft adds flexibility and character, and every space reflects the craftsmanship and thoughtful design found throughout the home. Outside, the setting is just as impressive, with beautifully kept grounds, and the rare advantage of a 45-foot boat slip that conveys with the sale-making this an exceptional opportunity for boating enthusiasts and those seeking the full Windmill Harbour lifestyle. A truly special harbourfront offering in one of Hilton Head Island's most coveted private communities.

1 Sailwing Lane, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$8,295,000
7 Beds 8 Baths HILTONHEAD-506356 MLS
Designed by renowned architect Bobby McAlpine, 26 Plum Thicket Road is a rare legacy property offering exceptional privacy, architectural significance, and one of the most coveted settings in Palmetto Bluff. Approached by a private bridge and set on expansive acreage, the estate creates a remarkable sense of arrival while overlooking the iconic par-3 14th hole of the May River Golf Course. Sweeping views extend from tee to green and beyond to the May River, with the 13th hole enhancing the surrounding Lowcountry landscape. McAlpine's timeless design is evident throughout the residence, where refined craftsmanship and authentic Lowcountry architecture come together effortlessly. Pine floors accented with bluestone, custom built-ins, detailed millwork, and thoughtfully curated finishes create an atmosphere that is both elegant and welcoming. Recently renovated, the home has been extensively refreshed with a full interior and exterior repaint, new Wolf and Sub-Zero appliances, custom lighting, and select structural improvements. The seven-bedroom compound offers exceptional flexibility, featuring four bedrooms in the main residence, a two-bedroom guest house, and a private suite above the three-car garage. Indoor living spaces flow seamlessly to expansive outdoor entertaining areas, including a resort-style pool, grilling station, and screened porch, all positioned to maximize the panoramic golf course and river views. 26 Plum Thicket Road presents a rare opportunity to own a stunning residence in the heart of Palmetto Bluff, where timeless architecture, privacy, and luxury Lowcountry living converge. Furnishings are negotiable, please inquire for details.

26 Plum Thicket Road, Bluffton

Listing courtesy of EXP Realty LLC.

$1,739,000
6 Beds 6 Baths HILTONHEAD-506891 MLS
Welcome to this exceptional coastal retreat in the private, gated community of Fish Haul on Hilton Head Island. Built in 2020, this stunning 6-bedroom, 5 full and 1 half bath home offers the perfect blend of luxury, comfort, and investment potential. Ideally located just moments from Fish Haul Beach, the property features beautiful Port Royal Sound views and is designed to accommodate large gatherings with ease. The spacious, thoughtfully designed layout includes expansive living areas, multiple porches and decks, and seamless indoor-outdoor living throughout. The chef's kitchen is equipped with high-end appliances, ample storage, and an open flow ideal for entertaining. The inviting living room provides the perfect setting for relaxing evenings, while the adjoining outdoor spaces offer plenty of seating and a grill for hosting. Step outside to your private backyard oasis featuring a heated saltwater pool, putting green, and lush landscaping. Multiple porches-some with charming swings-create peaceful spots to unwind and enjoy the coastal breeze. With upscale finishes, strong rental potential, and the ability to comfortably sleep large groups, this home is an outstanding investment opportunity or personal getaway. A rare offering in one of Hilton Head's most serene and sought-after neighborhoods. Strong Short Term rental numbers for 2026: over $160,000!! Fast walk to the beach with a brand-new board walk, grab your beach chair and be there in 3 minutes!

2 Talon Court, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

$1,895,000
4 Beds 3 Baths HILTONHEAD-505725 MLS
Perched above the May River in Historic Bluffton, this exceptional home captures the very best of Lowcountry living. Tucked away at the end of a quiet cul-de-sac in Martin's Place, it offers breathtaking May River views, unforgettable sunsets, and refreshing coastal breezes. The thoughtfully designed inverted floor plan places the great room, beautifully remodeled eat-in kitchen with high-end appliances and induction cooktop, office, and primary suite upstairs, where the scenery takes center stage. Relax on the classic double front porches full of Southern charm or unwind on the expansive rear deck overlooking the May River. Downstairs features three additional bedrooms plus the beloved "Oyster Room," a flexible gathering space perfect for entertaining after a day on the water. Additional highlights include an oversized garage, spray-foam insulated walk-up attic with expansion potential, and room for a pool. Martin's Place offers low HOA fees, a community dock with short-term docking privileges (up to 4 days/3 nights), and the rare ability to keep a trailered boat on your property-all just a short walk or golf cart ride to the restaurants, shops, galleries, parks, Farmers Market, and waterfront charm of Historic Old Town Bluffton.

44 Minuteman Drive, Bluffton

Listing courtesy of The Cobb Group brokered by eXp Realty.

$479,000
5 Beds 4 Baths HILTONHEAD-504448 MLS
Welcome to 61 Mary Elizabeth Drive, a spacious 5-bedroom home on Lady's Island featuring a large, fully fenced backyard perfect for pets, children, entertaining, gardening, or simply enjoying outdoor Lowcountry living. With plenty of room to spread out both inside and out, this home is ideal for growing families, multi-generational living, or those who need extra space for guests, a home office, or hobbies. This well-maintained home includes a first-floor primary suite, 3 full bathrooms, a half bath, formal dining room, spacious living area, upstairs loft, and convenient laundry room. The open-concept layout creates a natural flow between living, dining, and kitchen spaces, making everyday living and entertaining easy. Recent upgrades include stainless steel appliances less than two years old, a new garbage disposal, plush carpet with upgraded padding, and durable commercial-grade laminate flooring. Conveniently located on Lady's Island near shopping, dining, schools, downtown Beaufort, and local military bases, this property offers both comfort and convenience. Currently generating $2,800 per month in rental income, this home also presents an attractive investment opportunity. Assumable VA loan at 3.0 available with accepted offer and buyer qualification. Schedule your showing today!

61 Mary Elizabeth Drive, Beaufort

Listing courtesy of Charter One Realty.

$269,900
4 Beds 3 Baths HILTONHEAD-506859 MLS
Set within the storied contours of St. Helena Island in the distinguished enclave of Eddings Point, this Lowcountry residence rests with a kind of quiet confidence shaped by light, by space, and by the enduring rhythm of place. Thoughtfully and comprehensively reimagined, every element of the home has been redone and updated to reflect a refined, modern standard while honoring its setting. The land itself rests on 0.51 acres without the constraints of an HOA and offers a relaxed freedom, while the raised structure stands as both a nod to practicality and a thoughtful response to its coastal environment. Inside, light moves freely through the open layout, tracing the lines of fresh surfaces and modern finishes, each detail chosen with intention rather than excess. The living space centers around a sleek electric fireplace, showcasing an understated hearth that gathers the room without demanding attention, offering warmth both literal and symbolic. The kitchen, refined and deliberate, carries a quiet elegance. With its new stainless steel appliances and design, it invites both function and gathering, becoming less a place of task and more a place of continuity where memories begin and return. Beneath the visible transformation lies a deeper assurance. A new roof, new HVAC system, and new hot water heater provide a foundation of certainty, allowing the present to be lived fully. The home spans 2,508 square feet and offers four bedrooms, each carrying the same sense of thoughtful design and quiet refinement. The primary suite reads as a pause in the narrative; a private chapter written in softer tones. Here, a soaking tub, glass enclosed shower, and illuminated mirrors create a space not simply for routine, but for retreat and for the quiet reclamation of time. Among the home's more intimate details, a versatile room enclosed by glass screen doors opens gracefully toward the backyard deck, blurring the boundary between indoor and outdoor living, while the deck itself reaches into the open air where the backyard stretches with both intention and possibility. It is a space shaped not by limitation, but by potential, where evenings unfold slowly and the Lowcountry air carries its familiar, salt tinged calm, offering both privacy and the subtle promise of what could be further written here. Located just moments from the everyday offerings of Beaufort yet held within the calm of its own setting, the home exists in a balance between connection and retreat.

8 Jenkins Port Road, St Helena Island

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

$615,000
4 Beds 3 Baths HILTONHEAD-506830 MLS
Tucked away in the highly sought-after community of Victoria Bluff, this charming Lowcountry home offers a rare blend of privacy, nature, and convenience. With only 64 homesites and a low POA, Victoria Bluff is one of Bluffton's hidden gems - a quiet, wooded community surrounded by protected nature preserve and filled with the mature trees and timeless character that make the Lowcountry so special. This thoughtfully designed home features 3 bedrooms plus a versatile 4th room perfect for a home office, guest room, or flex space. The spacious first-floor primary suite offers convenience and privacy, while the additional bedrooms upstairs create a functional layout for family or guests. Bright, open living spaces flow effortlessly throughout the home, creating an inviting atmosphere ideal for both everyday living and entertaining. One of the standout features is the expansive screened-in porch that spans the full length of the home, providing exceptional outdoor living space and the perfect setting to relax and enjoy the peaceful surroundings. The fully fenced backyard adds privacy and convenience for pets or gatherings, while the detached two-car garage offers additional storage. Located on a quiet cul-de-sac beneath a canopy of mature trees, this property captures the serenity and natural beauty that are becoming increasingly difficult to find in Bluffton communities today. Residents enjoy direct access to the Victoria Bluff Heritage Preserve, complete with trails, abundant wildlife, and protected green space right outside their doorstep. For boating enthusiasts, the H.E. Trask, Sr. Public Boat Landing is just minutes away, making days on the water easy and accessible. Despite its secluded feel, Victoria Bluff offers a prime location just 10 minutes from the Hilton Head Island bridge and Historic Downtown Bluffton. Dining, shopping, and daily conveniences are moments away at Tanger Outlets while still maintaining the community's peaceful, wooded atmosphere. With its inviting layout, expansive outdoor living space, mature natural surroundings, and location within one of Bluffton's most unique small communities, this home is a rare opportunity to experience true Lowcountry living.

60 Old Sawmill Drive, Bluffton

Listing courtesy of Realty One Group - Lowcountry.

$1,625,000
4 Beds 4 Baths HILTONHEAD-503394 MLS
Stunning views of Millers pond that expands to Marsh views of Fish Haul Creek to Port Royal Sound. Enjoy colorful sunrises, watch the fish jump & the birds play amongst natures backdrop! Sunlit home features 4 bedrooms & 4 full baths. There is a spacious screened porch to enjoy the views. Large kitchen with gas stove top & walk in pantry that opens to the family room all with stunning views. Living room features a gas fireplace with a cathedral ceiling. Separate dining room for entertaining with lit tray ceilings. Wood floors in the living areas with carpet in the bedrooms. Large laundry room with a sink and storage. Enjoy sitting on the swing under the oak tree while you enjoy the ever changing backdrop of Millers Pond. There is an oversized 2 car garage. 4th bedroom can be used as a bonus room/office. This home is a short distance to the beautiful private beaches in Port Royal Plantation. Enjoy the Beach house, large oceanfront community pool, leisure trails tennis courts, pickleball courts, bike paths, arboretum and more. Freshly painted interior, New duct work 10/25 & well water for irrigation.

11 Outpost Lane, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$914,900
5 Beds 4 Baths HILTONHEAD-504643 MLS
Welcome to 28 Fairway Drive in Rose Hill Plantation, a sought-after golf community in Bluffton, SC. This beautifully updated 5BR/4BA home sits on the 13th fairway with stunning golf-to-lagoon views and western sunsets. The light-filled floor plan offers spacious living areas, a bright Carolina room, and seamless indoor-outdoor flow. Enjoy a private backyard with garden-style pool, expansive patio, and professional landscaping-perfect for relaxing or entertaining. Over $100K in improvements include a new roof, custom built-ins, shiplap fireplace, custom closets, improved drainage, and refreshed pool and landscaping. Two flexible upstairs bedrooms ideal for office, gym, or guests plus oversized walk-in attic storage. Rose Hill amenities include golf, 3 pools, equestrian facilities, deep-water access, clubhouse, tennis, pickleball, and trails. WELCOME HOME!

28 Fairway Drive, Bluffton

Listing courtesy of The Agency Hilton Head.

$2,200,000
4 Beds 6 Baths HILTONHEAD-506557 MLS
Exceptional NEW PROPOSED CONSTRUCTION home in Haig Point, located minutes from the private beach access. Award winning builders, Goodwin Custom Homes, proudly presents this 4-5 bedroom house with many customizations available. If you can imagine it, they can build it. Act fast to work with our interior designer to pick all interior selections. Discover refined coastal living with this thoughtfully designed construction in the sought-after Haig Point community on Daufuskie Island. Blending timeless Lowcountry architecture with elevated, designer-selected finishes, this home offers the perfect balance of sophistication and relaxed island living. The exterior showcases classic coastal charm with a combination of horizontal and vertical Hardie siding, oyster shell tabby foundation detailing, cedar corbels, and a standing seam metal roof accented by architectural shingles. A welcoming entry with custom doors in a soft Monticito mint hue creates an inviting first impression. Inside, the home features a light-filled, open-concept layout with European white oak flooring throughout and curated spaces designed for both everyday living and entertaining. The gourmet kitchen is highlighted by custom cabinetry, quartz countertops and backsplash, and a well-appointed scullery for additional prep and storage. Elegant design continues into the living and dining areas with custom trim details, a fireplace feature, and thoughtfully designed transitions between spaces. The primary suite offers a spa-inspired bath with a freestanding soaking tub, quartz surround, designer tile, and elevated fixtures, creating a serene retreat. Additional guest suites and baths are finished with carefully selected tile work, custom cabinetry, and stylish fixtures, while the 2nd floor boasts great entertainment space that provides flexibility for a media room, or lounge for gathering. Every detail of this home has been intentionally curated to reflect a clean, coastal aesthetic with warm textures, soft tones, and timeless finishes throughout. Enjoy the unparalleled lifestyle of Haig Point-featuring golf, tennis, water access, and the privacy of island living-all just a short ferry ride from Hilton Head. Goodwin Custom Homes has exclusive access to a number of lots in Haig Point. If this floor plan or lot does not suffice, reach out for other custom opportunities!

18 Freeport Drive, Daufuskie Island

Listing courtesy of Premier Properties by Haig Point.

$2,275,000
4 Beds 4 Baths HILTONHEAD-506548 MLS
Welcome to this beautifully reimagined luxury residence in the sought-after deep-water community of Spanish Wells, where timeless coastal elegance meets modern sophistication. This home was completely renovated in March 2026, showcasing exceptional craftsmanship & thoughtful design throughout. Upon entering, you are greeted by gorgeous solid white oak flooring that flows throughout the main level, creating a warm and refined atmosphere. The spacious living room, highlighted by a tray ceiling and natural light from newly installed windows, offers an inviting yet elegant setting for everyday living. At the heart of the home is the stunning chef's kitchen, beautifully appointed w/granite countertops, stainless-steel appliances & a professional-grade 6-burner double oven w/pasta filler faucet. A generous pantry & additional storage ensure both beauty & functionality. The kitchen opens seamlessly to the expansive great room, where vaulted ceilings & a striking brick wood-burning fireplace w/custom built-ins create a dramatic yet comfortable gathering space. Designed for effortless entertaining, the home also offers a private courtyard on one side & a large screened Carolina room on the other, perfect for enjoying the coastal climate year-round. A formal dining room just off the kitchen provides an elegant setting for hosting memorable dinners & celebrations. The open-concept layout blends modern luxury w/relaxed coastal living, making this home ideal for both entertaining & everyday comfort. The luxurious primary suite is a private retreat featuring an oversized walk-in closet w/a built-in closet system. The spa-inspired primary bath includes a freestanding soaking tub, separate shower, dual vanities, & a private water closet, offering a serene sanctuary. There are sliding doors that lead to the private courtyard, Also on the first floor is a newly constructed guest bedroom with a full bath, ideal for guests or multi-generational living. A laundry room & stylish half bath are conveniently located down the hall from the kitchen. Upstairs, two additional bedrooms w/new carpeting share a beautifully updated full bath, providing comfortable accommodations for family & visitors. This 4-bedroom, 3-bath residence sits on an expansive lot of just over one acre, offering privacy & space to enjoy Lowcountry living. The property features a circular driveway, a spacious two-car garage & RV parking pad with privacy fence! See list of additional features

13 Mcintosh Road, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

$2,100,000
4 Beds 5 Baths HILTONHEAD-505896 MLS
With four en-suite bedrooms and a tranquil lagoon backdrop, this home truly balances space and serenity. Brazilian oak hardwoods (2024) gleam throughout. The 2025 kitchen renovation and expansion create the perfect setting for both cooking and entertaining. New patio doors (2024) lead you out the expanded deck (2022) where you can relax and take in the beautiful views Sea Pines is so famous for providing. Truly, no stone was left unturned in maintaining and upgrading this home. A full list of upgrades/renovations as well as a pool rendering can be found in the home at your viewing or be made available upon request. Residents of Sea Pines enjoy natural beaches, championship golf courses, miles of bike paths, two marinas, an upscale beach club, shops and restaurants all in a gated community with 24/7 security. This is not an opportunity to miss!

46 Hearthwood Drive, Hilton Head Island

Listing courtesy of Collins Group Realty.

$750,000
5 Beds 4 Baths HILTONHEAD-506043 MLS
Formerly owned by Arthur B. Horne, this beautifully reimagined brick home is the perfect blend of history and modern comfort. Taken down to the studs and completely renovated. Updates include new roof, flooring, windows, doors, lighting, a full suite of appliances and core systems, including HVAC, electrical and plumbing. Situated on a 1-acre lot with an outdoor entertaining area, covered parking with car charging station, and brand-new septic system & well, this turnkey home offers space and peace of mind. The property features a fully equipped private apartment with 1 bedroom, kitchen, bathroom and living room. Perfect for creating a steady income stream! Make this your new home today!

656 Broad River Boulevard, Beaufort

Listing courtesy of Charter One Realty.

$6,500,000
5 Beds 5 Baths HILTONHEAD-505596 MLS
Positioned along one of Hilton Head Island's most coveted stretches of coastline, 9 Bayberry Lane offers a rare blend of privacy, architectural distinction, and timeless coastal elegance. Completed in 2019, the home showcases extraordinary craftsmanship and thoughtfully curated natural materials throughout. Spanning 5 bedrooms and 5 bathrooms, it was designed for both relaxed living and refined entertaining, featuring 2 luxurious primary suites with spa-inspired baths and ocean views. Soaring ceilings, bespoke finishes, and expansive gathering spaces create an atmosphere that is both sophisticated and inviting, while a screened porch and elevated ocean lookout provide the perfect vantage points to enjoy the ocean breeze and ever-changing coastal landscape.

9 Bayberry Lane, Hilton Head Island

Listing courtesy of Dunes Real Estate.

$698,000
4 Beds 4 Baths HILTONHEAD-505796 MLS
Welcome to 3 Canebrake Lane! Remodeled in 2025, this beautifully updated 4-bedroom, 3.5-bath home offers 2,347 square feet of comfortable living with exceptional bedroom separation and park views. Recent improvements include new LVP flooring, new roof, new HVAC, new granite countertops in the kitchen and all bathrooms, new GE stainless steel appliance package, fresh interior and exterior paint, three remodeled bathrooms, new carpet, updated lighting, ceiling fans, door hardware, and blinds. The thoughtfully designed floor plan features three bedrooms on the main level, including the primary master suite, plus a second master suite upstairs with its own full bath-ideal for guests or multigenerational living. The spacious kitchen opens to a cozy family room with a fireplace, while the rear patio offers peaceful views of the park and wooded surroundings. Detached full two-car garage, attic storage, a connecting breezeway, and a separate laundry room. 24-hour gated community with exceptional amenities including three pools, tennis and pickleball courts, neighborhood dock, park, walking trails, 18-hole golf course, and equestrian center. Backing directly to the neighborhood park, this home offers convenient access to scenic walks and outdoor enjoyment. Both Owners/Sellers are licensed South Carolina Real Estate Licensees.

3 Canebrake Lane, Bluffton

Listing courtesy of RE/MAX Island Realty.

$2,099,000
5 Beds 4 Baths HILTONHEAD-505477 MLS
Pristine finishes and meticulous craftsmanship define this newly renovated Sea Pines home. Thoughtfully redesigned with a second-floor addition, the now five-bedroom, four-bath residence offers refined coastal living with beautifully curated interiors and exceptional outdoor spaces. A resort-style pool and expansive decking with sleek cable railings create a retreat surrounded by a tranquil Lowcountry landscape. Inside, abundant new windows fill the open-concept living spaces with natural light, highlighting the oak flooring and clean architectural lines. The kitchen features quartz countertops, custom soft-close cabinetry, and a full suite of KitchenAid appliances centered around a generous island. The adjoining living and dining areas flow effortlessly to the outdoor living spaces. Each of the four bathrooms has been thoughtfully finished with designer tile, modern fixtures, and spa-inspired details, while the spacious bedrooms provide comfort and flexibility for both family and guests. The primary suite has a beautifully appointed ensuite bath and generous storage. Located within the gates of Sea Pines Resort, this home places you moments from the best of Hilton Head Island living. Miles of shaded bike trails, world-class golf including Harbour Town Golf Links and Atlantic Dunes, the Sea Pines Racquet Club, and the renowned Sea Pines Beach Club are all within easy reach. This property also presents a compelling short-term rental opportunity in one of the island's most sought-after vacation destinations

72 Lawton Road, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

$2,960,000
5 Beds 5 Baths HILTONHEAD-505522 MLS
Coastal splendor meets modern luxury in this freshly renovated 5 bedroom, 5 bath Palmetto Dunes home. Positioned fourth row ocean, this Low Country style property is a true self contained resort just steps from the southeast's favorite beach. The newly imagined interior boasts family gathering areas framed by ample natural light and beautiful wood flooring, while the expanded chefs kitchen showcases new appliances, quartz counters and ample storage. Guests will delight in the private swimming pool and expansive deck, all with striking views of Palmetto Dunes' saltwater lagoon system and centuries old oaks. The home's new screened porch is the ideal spot to recap the day's activities, all while enjoying cocktails and seafood boils under the night's early stars. Outdoor sports enthusiasts will love the spacious garage featuring a second laundry facility, full bathroom and large flex storage room. The home's newer roof, pex plumbing, home elevator and automated hurricane shutter protection allow for complete piece of mind. Classic styling and modern convenience blend perfectly with the bounty of Palmetto Dunes' resort offerings to create the ideal primary residence, second home or investment property.

153 Mooring Buoy, Hilton Head Island

Listing courtesy of The Hilton Head Agency.

$2,195,000
4 Beds 4 Baths HILTONHEAD-505673 MLS
A Rare Point Comfort Peninsula Property. Tucked away on one of the most remarkable homesites on Hilton Head Island, this classic coastal home sits on approximately 1.25 acres at the end of a private peninsula, surrounded by over 180 degree views of marsh and deep water. Properties with this combination of land, privacy, and views are extraordinarily rare on the island today. Even more rare is the Point Comfort lifestyle, a relaxed authentic Lowcountry way of living. Residents can enjoy access to the community boat landing w/ direct water access, allowing you to keep your boat right at home then head out on the water whenever the tide and weather call. Enjoy golf cart rides and spend time with neighbors within this friendly enclave, a place where life moves at an easy pace. Built during the island's early era of thoughtful coastal contemporary design in the 1960s, the home reflects the architectural style that helped define Hilton Head, simple, understated Lowcountry modernism designed to live in harmony with the landscape. Large windows frame the water and marsh from nearly every angle, while the open floor plan invites the outdoors inside, capturing the island's breezes, light, and ever-changing skies. The setting is nothing short of magical. World-class sunsets stretch across the marsh each evening, casting warm light across the water and surrounding vegetation. Mature trees and natural landscaping create a sense of privacy that is increasingly difficult to find on the island. Inside, the two-story layout offers generous living space and flexibility. The main living areas are designed for relaxed coastal living and entertaining, while the lower level provides ideal accommodations for a mother-in-law suite, multi-generational living or just additional living/office space. Step outside to a large private patio, perfect for quiet mornings. Enjoy the sunset from the second floor deck. A private drive leads to the home and carport, further enhancing the sense of seclusion. For decades, this home has been the backdrop for generational memories-family gatherings, sunset dinners, and life along the water. It now awaits its next steward to continue that tradition. With low annual dues $500.00, minimal restrictive covenants, extraordinary land size, sweeping water views, and unmatched natural beauty, this Point Comfort property represents a truly unique opportunity on Hilton Head Island.

18 Nautilas Road, Hilton Head Island

Listing courtesy of SERHANT.

$1,899,000
4 Beds 3 Baths HILTONHEAD-505517 MLS
Unbelievable Oceanfront Views with Private Beach Access! Experience the ultimate coastal lifestyle in this one-of-a-kind Fripp Island retreat. This stunning single-level home showcases breathtaking, panoramic ocean views from the primary suite, great room, and guest bedroom, allowing you to enjoy the beauty of the Atlantic from nearly every room. Step inside to soaring 14-foot ceilings in the great room, creating a bright and open living space filled with natural light and scenic ocean views. The open-concept layout features hardwood floors, gas fireplace, and a well-appointed kitchen that flows seamlessly into the main living areas. The spacious primary suite offers a private sitting area, large walk-in closets, and, of course, more sweeping ocean views. Enjoy mornings or evenings on the expansive screened-in porch and adjoining deck overlooking the beautifully manicured yard and the beach beyond. Additional highlights include convenient walk-up attic storage and a spacious garage that can accommodate 3-4 cars or golf cart, with ample room for a finished game room, workshop, or additional storage. A truly exceptional oceanfront property!

11 River Club Drive, Fripp Island

Listing courtesy of Charter One Realty.

$3,995,000
7 Beds 7 Baths HILTONHEAD-505616 MLS
Turnkey short- term rental with proven income history in top tier coastal market! Secure a vacation home that offsets its costs. Professional property management used for rentals. LARGEST 2ND ROW HOME ON THE MARKET! Extensively renovated in 2024! Grossed $246K in rentals for 2025. Stunning home features 7 BR, 61/2 BA & offers a perfect blend of luxury, comfort, & breathtaking ocean views. Located in the coveted North Forest Beach, near Coligny Plaza, this home provides a balance of privacy & proximity to the beach. The open living & dining areas feature stunning direct ocean views, natural light creating a warm & inviting beach atmosphere. New roof, paint, pool deck, game area, outdoor spa, landscaping & many more improvements. Enjoy relaxing by the elevated pool, soak in the hot tub or grill in the private outdoor area! Directly across street to beach access!

8 Curlew Road, Hilton Head Island

Listing courtesy of Hilton Head Real Estate Partners.

$1,025,000
4 Beds 4 Baths HILTONHEAD-505127 MLS
Classic Lowcountry charm meets privacy and sweeping golf views in this beautifully maintained home set on over one acre on Callawassie Island. Positioned more than 300 feet from the road along a tree-lined, landscaped drive, the home offers exceptional curb appeal and a peaceful setting overlooking the recently renovated Dogwood golf course. The thoughtfully designed floor plan features 4 bedrooms and 3.5 baths, including a spacious first-floor primary suite and a dedicated office. Upstairs guest bedrooms and a versatile bonus room provide comfortable space for family or visitors. Hardwood floors, custom built-ins, detailed millwork, and numerous walk-in closets enhance the home's character and functionality. Floor-to-ceiling windows along the rear of the home fill the living spaces with natural light and showcase the beautiful golf course views, while the screened porch offers the perfect place to relax and enjoy the professionally landscaped yard. A wonderful opportunity to enjoy classic Lowcountry living in the sought-after community of Callawassie Island.

50 Spring Island Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$3,950,000
6 Beds 7 Baths HILTONHEAD-505514 MLS
Discover the ultimate second-row ocean escape in Palmetto Dunes where luxury living meets effortless beach access. This turnkey home, 5 Brigantine, is an exceptional opportunity as a vacation home, rental investment, or primary residence, accommodating up to 18 guests, complete with a private pool & spa and ideally positioned across the street from the dedicated beach path. This expansive property offers 6 bedrooms and 6.5 baths, including a separate guest house for added flexibility and privacy. The first-floor features three spacious bedroom suites: one with its own sitting/TV room and direct pool access for a private retreat, a second with pool access, and a third designed with younger guests in mind, offering two beds plus a trundle. The second floor is the heart of the home making it perfect for entertaining and gathering. A bright, open-concept living room, kitchen, and dining area surrounded by windows and sliding doors flood the space with natural light. Multiple outdoor decks extend from the main living area and bedrooms, creating seamless indoor-outdoor living. This level also includes the primary suite and an additional guest ensuite. For a special vantage point, the third-floor cupola and outdoor sitting area provides a peek of the ocean and coastal breezes, ideal for relaxing evenings and sunset cocktails. Across the breezeway, the guest house offers a private suite with a king bed, sleeper sofa, full bath and mini kitchenette - perfect for visiting family and friends. Additional highlights include LVP flooring throughout, a gas fireplace, quartz countertops, stainless steel appliances, gas cooktop, a two-car garage, and a deep driveway with ample guest parking. All of this within one of Hilton Head Island's most sought-after ocean-oriented communities.

5 Brigantine, Hilton Head Island

Listing courtesy of Keller Williams Realty.

$3,250,000
4 Beds 5 Baths HILTONHEAD-505022 MLS
This gorgeous home is uniquely situated on nearly an acre homesite in Sea Pines with a long scenic driveway that meanders under towering oaks to a grand entrance. Enjoy privacy with minimal care in this natural landscape environment. The quality craftsmanship features shiplap, beams, heart of pine flooring, chef's kitchen, an elevator, and multiple fireplaces. Both rear porches and a lower poolside terrace overlook a backyard swimming pool and the tidal salt marsh stretching out to Calibogue Sound and the intracoastal waterway. Beautifully updated with state of the art appliances and gas cooktop, the kitchen opens to the dining and great room with beautiful views to the marsh and sound. The current owners have continued to update and beautifully maintain this masterpiece of southern charm. Don't miss the second laundry room downstairs - perfect for towels from the pool and beach. Additionally, there is a recreation room and full bath downstairs for easy access from the pool.

20 Oyster Landing Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

$1,050,000
3 Beds 4 Baths HILTONHEAD-505303 MLS
Light, bright & charming, this 3 bedroom, 3 1/2 bath home in private Long Cove Club is waiting to be yours. Elevated, on a corner lot & cul de sac road with tranquil lagoon view. Interior features include a cathedral ceiling & wall of windows in the family room with a beautiful stone gas fireplace. Other features include custom woodwork, generous granite kitchen island and dining area, stainless steel appliances, tile floors on the main living area. The en suite primary bedroom with granite is also on the main level. Second floor has 2 spacious en suite bedrooms. A sizeable deck with a Sunshade awning overlooks the lagoon. Air conditioned & heated large storage room is off the ample 2 car garage. As a LCC resident, you will enjoy the world class amenities which include the Pete Dye designed golf course, deep water marina, tennis, full service clubhouse, community pool, pickleball & bocce ball. There are many group activities within the Club. This home has been well maintained, enjoyed & loved by the owners as a second home. Excellent condition throughout the home.

1 Foot Point Road, Hilton Head Island

Listing courtesy of Howard Hanna Allen Tate Lowcountry.

$1,890,000
4 Beds 4 Baths HILTONHEAD-504585 MLS
Enjoy exceptional waterfront living on Callawassie Island with rare western exposure and unforgettable sunset views over the tidal marshes of Chechessee Creek, complemented by peaceful water and golf views from the front of the home. Privately positioned, this pristine custom-built residence offers a true Lowcountry lifestyle with a private short dock, floating dock, and new boat lift providing direct water access for boating, kayaking, and sunset cruises. Designed for both everyday comfort and effortless entertaining, the open floor plan is centered around a chef's kitchen featuring Wolf and Sub-Zero appliances, a 10-foot island, beverage bar, wine cooler, and ice maker. Wide plank hardwood floors flow throughout the main living areas, while two first-floor guest suites offer beautifully remodeled en suite baths for privacy and convenience. Thoughtful improvements enhance both form and function, including a newer roof, new deck and shutters, a custom-built fireplace with new insert, replaced interior doors, all new water piping, spray foam insulation in the crawl space, new crawl space screening, updated lighting, refreshed landscaping, and a full exterior repaint in 2025.Expansive outdoor living spaces capture sweeping marsh views and glowing sunsets, creating a serene and private backdrop that changes with the tides and seasons. Residents enjoy the unmatched lifestyle of Callawassie Island-an engaging community, remarkable natural beauty, top-tier golf and amenities, endless outdoor activities, and the peace of mind that comes with gated security and true Lowcountry privacy.

41 Sugar Mill Drive, Okatie

Listing courtesy of Coastal Real Estate Solutions II.

$331,000
3 Beds 2 Baths HILTONHEAD-505169 MLS
Step out of your DeLorean and back to 1987 at 49 Heron Walk on Callawassie Island. Perfectly positioned on the tee box of the first hole of the Dogwood Course, this classic golf cottage delivers a true front-row seat to opening drives and glowing morning sunrises over the fairway. Lovingly maintained in remarkable original condition (with updated mechanicals), the home features warm woodwork, comfortable living spaces, and authentic 80s character throughout. Enjoy it just as it is, or modernize to your taste-either way, you're starting with an unbeatable golf course setting and timeless island appeal. Live here full time or create income as a sought-after retreat for visiting golfers-no flux capacitor required. Great Scott, this is island living with timeless style. Optional Golf.

49 Heron Walk, Okatie

Listing courtesy of Moul, REALTORS®.

$1,999,000
4 Beds 5 Baths HILTONHEAD-505035 MLS
Discover the ultimate blend of comfort, location, and income potential in this beautifully updated 4-bedroom, 4.5-bath home in the heart of Palmetto Dunes Resort. Perfectly positioned along the renowned 11-mile lagoon system, this property offers tranquil water views, privacy, and direct access to one of the island's most sought-after outdoor amenities.Designed for both relaxation and entertaining, the home features a heated pool and spa overlooking the lagoon - an ideal setting for enjoying coastal breezes or unwinding after a day at the beach. Inside, the remodeled kitchen shines with updated finishes and modern functionality, creating a welcoming space for gathering with family and guests. A recently added fourth full bathroom enhances comfort and convenience, while the flexible den/office-currently used as an additional sleeping area-adds valuable versatility for owners and renters alike.With four spacious bedrooms, 4.5 baths, and multiple living areas, the layout comfortably accommodates larger groups, making it a standout performer in the short-term rental market with strong, consistent income.Just a short bike ride to the beach and moments from world-class golf, tennis, pickleball, dining, and marina access, this lagoon-front retreat offers the very best of Hilton Head Island living - whether as a primary residence, second home, or investment property.

73 Port Tack, Hilton Head Island

Listing courtesy of ERA Wilder Realty, Inc.

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