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19 Wexford Club Drive, Hilton Head Island
$2,995,000
ACTIVE Status ⋅ 4 Beds ⋅ 6 Baths ⋅ 6,572 SqFt. ⋅ HILTONHEAD-508097 MLS
Set on nearly 0.70 acres in the heart of Wexford, this distinctive estate-sized golf course home offers an exceptional combination of architectural character, privacy, and the sought-after lifestyle of one of Hilton Head Island's premier private club communities. A sweeping horseshoe driveway, framed by mature landscaping, leads to a secluded courtyard and a welcoming entry. Unique architectural details define the home, including a dramatic barrel ceiling with skylight in the foyer, antique doors, rich reclaimed-wood flooring, and impressive vaulted ceilings. The expansive great room is designed for both grand entertaining and comfortable everyday living, with multiple seating and dining areas, space for a baby grand piano, a massive stone fireplace, and seamless access to outdoor living. The adjacent chef's kitchen features a breakfast area, walk-in pantry, and direct access to the covered outdoor dining area. The private primary suite includes a sitting area surrounded by floor-to-ceiling windows, a distinctive cross-vaulted ceiling, direct pool and spa access, oversized and secondary walk-in closets, private laundry, and well-appointed bath with soaking tub and separate water closet. Additional living spaces include a remarkable lower-level bar/gameroom or collector's room with vaulted ceilings, exposed beams, built-in bar, intricate fireplace, courtyard access, and full bath. Above the oversized 3-car garage are a spacious fitness room or den and two ensuite bedrooms, including one with a private deck. A fourth guest suite features an ensuite bath, generous closet space and French doors to the courtyard. The private backyard is beautifully positioned along the golf course while surrounded by mature landscaping for exceptional privacy. A secluded pool and spa, covered dining area, and additional deck create a peaceful outdoor retreat. Additional features include an oversized three-car garage, workshop, wine storage, and dual laundry areas. Wexford members enjoy a premier private club lifestyle with a private marina, championship golf, Har-Tru tennis, pickleball, croquet, resort-style pools, clubhouse dining, community fire pit, and year-round social activities. The new Harbour Center and expanded Clubhouse add even more gathering and social spaces at the center of the community. A rare opportunity to own an architecturally distinctive luxury golf course home in a gated private club community with marina access on Hilton Head Island.

19 Wexford Club Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

59 N Calibogue Cay Road, Hilton Head Island
$7,800,000
CLOSED Status ⋅ 5 Beds ⋅ 6 Baths ⋅ 5,580 SqFt. ⋅ HILTONHEAD-508090 MLS
Quite simply, one of the finest homes to come on the market in Sea Pines in many years. This luxury custom home, completed in 2022 by Esposito Builders and masterfully designed by architect Terry Rosser, is set along the highly coveted Calibogue Cay, an address reserved for a select few. Sweeping marsh vistas and extraordinary sunsets create a setting that is both serene and unforgettable. Dramatic 20+ ft ceilings span the living room, kitchen, and breakfast nook, filling the space with natural light and drawing your eye straight to the marsh beyond. The kitchen is beautifully executed and opens to a refined entertaining space with a wet bar, glass-front cabinetry, and a well-appointed butler's pantry. Just off the main living area, the screened porch with fireplace offers a comfortable, private retreat you will enjoy year round. The outdoor setting is equally impressive. A generous saltwater pool, private dock, and boat lift are perfectly positioned to capture long marsh views and remarkable sunsets. The primary suite is a true retreat, with expansive his-and-her walk-in closets, separate vanities, and a convenient Primary Laundry Room. Five bedrooms, along with a private executive office overlooking the marsh and sound, provide both scale and flexibility. Additional features include a 3-stop elevator, whole-house generator, and an oversized 2+ car garage with climate-controlled storage. Opportunities like this are few and far between. This is Calibogue Cay at its absolute best.

59 N Calibogue Cay Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - The Cottage Group, LLC. Selling Office: Keller Williams Realty.

54 Sparwheel Lane, Hilton Head Island
$3,000,000
CLOSED Status ⋅ 5 Beds ⋅ 6 Baths ⋅ 5,200 SqFt. ⋅ HILTONHEAD-507766 MLS
This еxceрtіonаl ΝΕW COΝЅTRUCTION end-unіt sеmi-detached residence offers an unparalleled blend of luxury, space, and breathtaking panoramic marina views stretching out to the Intracoastal Waterway. Boasting 5 bedrooms, 5.5 baths, and over 5,200 heated square feet, this home is thoughtfully designed for both refined living and effortless entertaining. Inside, the main living areas are anchored by stunning 7-inch white oak flooring, creating a warm and sophisticated backdrop. A beautifully appointed interior fireplace enhances the inviting atmosphere, while expansive windows frame serene waterfront vistas. The chef's kitchen is a true showpiece, featuring custom inset cabinetry with fully integrated paneled appliances, sleek stainless appliances, and meticulous craftsmanship throughout. Adjacent, a well-equipped wet bar and scullery with a striking wine tower provide both functionality and elegance for hosting. A dedicated office offers a quiet retreat for work or study, while the home's four-stop elevator ensures seamless access to every level. The primary suite is a private sanctuary, highlighted by a spa-inspired bathroom featuring a luxurious wet room clad in floor-to-ceiling Italian marble. Every bathroom in the home showcases Italian marble flooring, reinforcing the property's elevated design. The expansive bonus room is ideal for entertaining, complete with its own wet bar and beverage center, making it perfect for gatherings or relaxed evenings at home. Outdoor living is equally impressive, with three spacious marble-floored patios that overlook the marina and provide sweeping views out to the ICW-perfect for enjoying coastal breezes and unforgettable sunsets. An additional exterior fireplace creates a cozy ambiance for year-round enjoyment. Located within the prestigious Windmill Harbor community, residents enjoy access to a 15.5-acre lock-controlled marina with immediate Intracoastal Waterway access. Amenities include an Olympic-size pool, tennis courts, a fitness center, and proximity to the South Carolina Yacht Club, offering a truly elevated coastal lifestyle. This remarkable property seamlessly combines timeless design, modern luxury, and an unbeatable waterfront setting.

54 Sparwheel Lane, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty. Selling Office: William Raveis - Carolina LLC.

21 Belted Kingfisher, Hilton Head Island
$7,000,000
CLOSED Status ⋅ 4 Beds ⋅ 4 Baths ⋅ 5,194 SqFt. ⋅ HILTONHEAD-506820 MLS
Rare oсeanfront lаnd. Εxсерtiοnаl privacy. Substаntiаl construction. Irreplaceable location. Immediate enjoyment with unlimited future potential.Set on just over one-half acre near South Beach in Sea Pines, this one-owner oceanfront residence offers 5,000 square feet of thoughtfully designed living space, direct beach access and a private heated pool.The flexible floor plan features four bedrooms, including two arranged as a connected two-room suite-ideal for children, extended family, guests, a nursery or a private sitting room. Additional spaces include three-and-one-half baths, a dedicated office, media room, craft room, two fireplaces and an expansive primary suite with a private ocean-facing terrace.High ceilings, generous room proportions and abundant natural light provide an impressive foundation for creating a sophisticated coastal retreat with an easy walk to the Salty Dog, pickleball and all South Beach has to offer! Enjoy the home immediately while personalizing it over time, or use it as your oceanfront residence while planning a future custom estate.Privately positioned along Hilton Head Island's most desirable stretches of coastline, this property offers a substantial, well-maintained home, private pool and direct beach access to enjoy from day one-along with the land, location and flexibility to create your own long-term vision.A rare opportunity to own a significant oceanfront property where immediate enjoyment and extraordinary future potential come together.

21 Belted Kingfisher, Hilton Head Island

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

144 Harbour Passage, Hilton Head Island
$2,945,000
ACTIVE Status ⋅ 5 Beds ⋅ 7 Baths ⋅ 6,384 SqFt. ⋅ HILTONHEAD-507058 MLS
Four levels of harbour living distinguish this substantial Windmill Harbour residence, offering 6,384 sq. ft., elevator access throughout, protected harbour and Intracoastal views, and exceptional flexibility for boating, guests, work and recreation. The ground level is designed as a private Harbour Club, with an oversized tandem 2-car garage plus separate 1-car garage, leisure room with wet bar, utility room, guest suite with ensuite bath, covered patio and direct access to the waterfront setting. Additional conditioned rooms may serve as fitness, studio, workshop, storage or guest spaces. Conceptual renderings are in pictures. The main living level is centered around a chef's kitchen and includes a formal dining room, parlor, office, great room, half bath, rich wood flooring, extensive millwork and a broad balcony overlooking the harbour. One level above, the expansive owner's suite features two walk-in closets, a private bath and balcony access, accompanied by three additional ensuite bedrooms, a laundry room, secondary kitchenette and another generous harbour-facing balcony. The top floor creates an additional entertainment destination with a large family or media room, two flexible rooms, a shared bath and elevator access- well suited for a private theatre, game lounge, office or extended-stay accommodations. Windmill Harbour is one of Hilton Head Island's most distinctive private communities, built around a protected inland harbour and lock-controlled marina with direct access to the Intracoastal Waterway. The South Carolina Yacht Club offers dining, fitness, swimming, tennis, pickleball, yachting events and an active social calendar. Rarely does a home combine this scale, guest capacity, storage, garage space and harbour lifestyle in one residence.

144 Harbour Passage, Hilton Head Island

Listing courtesy of Coldwell Banker Access Realty.

752 Colonial Drive, Hilton Head Island
$1,995,000
CLOSED Status ⋅ 5 Beds ⋅ 6 Baths ⋅ 5,000 SqFt. ⋅ HILTONHEAD-506372 MLS
Welcome to an exceptional opportunity in the private Golf Club at Indigo Run, where timeless design meets impeccable care. Perfectly positioned on a beautiful homesite overlooking the 16th green, this stunning 5-bedroom, 5.5-bath residence offers over 5,000 square feet of thoughtfully designed living space and a rare level of privacy and tranquility. From the moment you arrive, the paver driveway and pristine exterior set the tone for what's inside-this home has been immaculately maintained and presents in truly exceptional condition. Every detail reflects quality, from the extensive high-end woodworking and custom trim throughout to the show-stopping great room featuring a striking custom cupola domed ceiling that creates both grandeur and warmth. Designed for both everyday living and effortless entertaining, the expansive screened back porch is a true highlight, complete with a built-in grill and fireplace-perfect for enjoying Lowcountry evenings while taking in serene golf views. The seamless indoor-outdoor flow continues to a beautifully finished paver patio, offering even more space to relax and gather. Inside, the layout offers incredible bedroom separation, providing comfort and privacy for family and guests alike. Each bedroom is generously sized with its own en-suite bath, while additional features like climate-controlled storage and a spacious 3-car garage add convenience and functionality. Homes of this caliber-so meticulously cared for, thoughtfully designed, and ideally located-rarely come to market. This is one you truly need to experience in person to fully appreciate the craftsmanship, condition, and setting.

752 Colonial Drive, Hilton Head Island

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

50 N Calibogue Cay Road, Hilton Head Island
$3,300,000
CLOSED Status ⋅ 4 Beds ⋅ 4 Baths ⋅ 5,034 SqFt. ⋅ HILTONHEAD-505597 MLS
Rare opportunity to own a spectacular Lowcountry marshfront deepwater estate on nearly an acre along one of Sea Pines' most coveted streets. This fully reimagined 5,034-square-foot residence blends luxury, privacy, and breathtaking coastal scenery. The home features a first-floor primary suite, three guest retreats, den, elevator, and a chef's kitchen appointed with GE Monogram appliances. An expansive enclosed heated pool and recreation area, outdoor grilling space, and private dock with direct access to the Atlantic Ocean create an exceptional waterfront lifestyle. Rebuilt from the studs, the residence offers all new electrical, plumbing, HVAC, and spray-foam insulation, along with bamboo flooring, designer lighting, and walls of glass that fill the home with natural light. Open living spaces flow seamlessly to the pool enclosure and waterfront dock-perfectly designed for effortless entertaining and unforgettable Lowcountry living. Your coastal life begins here!

50 N Calibogue Cay Road, Hilton Head Island

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

15 Man O War, Hilton Head Island
$7,650,000
CLOSED Status ⋅ 5 Beds ⋅ 8 Baths ⋅ 5,688 SqFt. ⋅ HILTONHEAD-505649 MLS
Rare opportunity to own a 5-bedroom oceanfront home on highly sought-after Man O War Street in Palmetto Dunes. Perfectly positioned along the beautiful Atlantic shoreline, this spacious coastal retreat offers stunning ocean views and effortless beach access. The open floor plan is designed for comfortable living and entertaining, with generous living areas and abundant natural light. Step outside to your private oceanfront pool and expansive outdoor spaces ideal for relaxing or hosting family and friends. Located in one of Hilton Head Island's most desirable resort communities, this property offers incredible potential as a short-term rental or the perfect forever home by the sea. Enjoy world-class beaches, golf, tennis, dining, and all that Palmetto Dunes has to offer just moments away.

15 Man O War, Hilton Head Island

Listing courtesy of Dunes Real Estate. Selling Office: Luxury Homes of Hilton Head.

17 Marsh Drive, Hilton Head Island
$5,250,000
CLOSED Status ⋅ 5 Beds ⋅ 6 Baths ⋅ 6,236 SqFt. ⋅ HILTONHEAD-505620 MLS
17 Marsh Drive offers front row seats to one of the most iconic stretches of golf at Harbour Town Golf Links. Perfectly positioned between the 16th green and 17th tee, the home enjoys sweeping views toward the famed 18th fairway and out to Calibogue Sound, all without interruption from cart paths or tournament grandstands. Custom built with 5 bedrooms and 5.5 baths, plus a bonus room over the garage and a main-level den/office, the home is designed for entertaining and comfort. The living room offers two sitting areas, fireplace, and an impressive wet bar with built-in wine cooler, sink, and ice maker. The kitchen features stainless steel appliances and a 6-burner gas range. A newly felt-covered pool table adds another space for gathering and fun. Walls of windows open to multiple outdoor living areas centered around a heated pool and separate in-ground spa. The primary suite is a private retreat with fireplace, spa-style bath with steam shower, and a remarkably large walk-in closet worthy of a luxury boutique. Situated on a peaceful residential street just off Plantation Drive near the historic Baynard Ruins, ownership includes access to the Baynard Cove Pavilion amenity park, where owners may host private events, launch kayaks or crab traps from the community dock, and store kayaks. A stunning setting with breathtaking sunsets over Calibogue Sound. This is an exceptional opportunity to enjoy front row golf views with this timeless Harbour Town setting.

17 Marsh Drive, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - The Cottage Group, LLC. Selling Office: ERA Wilder Realty, Inc.

8 Curlew Road, Hilton Head Island
$3,733,000
CLOSED Status ⋅ 7 Beds ⋅ 7 Baths ⋅ 5,462 SqFt. ⋅ HILTONHEAD-505616 MLS
Turnkey ѕhort- term rеntаl with рrοvеn inсοme history in toр tiеr 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. Selling Office: COAST PROFESSIONALS Brokered by EXP Realty.

25 Cotesworth Place, Hilton Head Island
$1,485,000
CLOSED Status ⋅ 5 Beds ⋅ 5 Baths ⋅ 5,123 SqFt. ⋅ HILTONHEAD-505313 MLS
A rare opportunity awaits at 25 Cotesworth Place, a one-of-a-kind 5-bedroom residence in the prestigious Indigo Run community of Hilton Head. With over 5,100sqft of refined living space, this home blends timeless architecture with exceptional privacy on a premium golf-course lot. Inside, generous gathering spaces, high ceilings, and thoughtful craftsmanship make this property ideal. Gourmet kitchen includes high end appliances such as Fulgor, Bosch, Viking and LG. Find a spacious master suite on the first floor with an updated master bathroom oasis. Two separate living areas downstairs with a large office and expansive screened-in porch overlooking the 16th fairway. Upstairs find 3 additional bedrooms, a spacious loft and two walk-in attic spaces for storage. Expansive windows frame serene fairway views, while the grandfathered-in fenced backyard creates a secluded retreat perfect for outdoor living, pets, and play. A home of this scale and setting is truly unmatched in Indigo Run.

25 Cotesworth Place, Hilton Head Island

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

1 Bridgetown Road, Hilton Head Island
$4,200,000
CLOSED Status ⋅ 6 Beds ⋅ 7 Baths ⋅ 5,177 SqFt. ⋅ HILTONHEAD-504819 MLS
Located in the prestigious gated community of Wexford, this exceptional waterfront residence offers breathtaking harbor views and refined Lowcountry elegance. Designed with modern sophistication, the home features open-concept living spaces, a primary suite on the main level, a private office, media room, and fitness room. Multiple decks and a screened porch provide seamless indoor-outdoor living. The expansive outdoor setting is highlighted by a well-appointed kitchen, travertine hardscaping throughout the driveway and patios, a plunge pool, fire pit, and a private dock. Residents enjoy access to Wexford's premier amenities and an unparalleled coastal lifestyle.

1 Bridgetown Road, Hilton Head Island

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

754 Colonial Drive, Hilton Head Island
$1,885,000
CLOSED Status ⋅ 5 Beds ⋅ 5 Baths ⋅ 5,779 SqFt. ⋅ HILTONHEAD-504152 MLS
Welcome to 754 Colonial Drive in the prestigious Golf Club neighborhood of Indigo Run on Hilton Head Island. This stunning 5 bedroom, 5 bathroom residence offers elegant Lowcountry living in one of the island's most sought after private communities. Designed for both everyday comfort and entertaining, the home features spacious main living areas filled with natural light and sweeping golf views. An upstairs second living and entertaining space provides flexibility for gatherings, media, or guests. The private fifth bedroom over the garage offers its own living area and full bath, creating an ideal guest suite, in law retreat, or private office setup. Outdoor living is equally impressive with a beautiful pool and expansive patio overlooking the 16th green of The Golf Club at Indigo Run. A magnificent live oak anchors the front yard, delivering timeless Southern curb appeal and a true sense of arrival. Positioned on a premier golf course homesite within a secure gated community, this property combines privacy, scenery, and lifestyle just minutes from dining, shopping, and the beaches of Hilton Head. A rare opportunity to own on one of Indigo Run's most desirable streets.

754 Colonial Drive, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty. Selling Office: The Agency Hilton Head.

39 Seabrook Landing Drive, Hilton Head Island
$3,299,999
CLOSED Status ⋅ 5 Beds ⋅ 6 Baths ⋅ 6,340 SqFt. ⋅ HILTONHEAD-503924 MLS
39 Seabrook Landing is a slice of heaven on earth with stunningly, spectacular, views across the ICW and Port Royal Sound to the Broad River Bridge. Imagine daily living with the magic and inspiration of soaring eagles, playful dolphins, migratory birds, sailing vessels and breathtaking sunsets over Pinckney Island. 6300 SF of casual elegance exudes with classic, timeless upgrades in 2025. Featuring 5 bedrooms, 4 Full BA, 2 HB, large library, office, home theater w/sitting room, formal LR and DR with coffered ceilings featuring low country inspired wall mural. Gourmet kitchen with huge Italian marble island and countertops, gas cooktop, pot filler, wine cave, eat-in kitchen, walk in pantry and butler's pantry, impressive foyer entry with sweeping curved staircase, picture moldings, built-ins, designer light fixtures, 3 fireplaces, heart of pine floors, family room, 3 screen porches! Large 1st floor primary w/fireplace, sitting area, full & half bath, two walk in closets and private screen porch. This home oasis is situated on almost one acre which affords a great deal of privacy with salt water pool, spa, and covered gazebo. Bulkheaded on a tidal creek for fantastic fishing and kayak launching. Long tabby drive way and 3 car garage. Seabrook Landing has a private day dock for Seabrook residents.

39 Seabrook Landing Drive, Hilton Head Island

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

47 River Club Drive, Hilton Head Island
$3,875,000
PENDING Status ⋅ 5 Beds ⋅ 6 Baths ⋅ 6,330 SqFt. ⋅ HILTONHEAD-504359 MLS
Claim Thе Water at 47 Rіvеr Club Drivе, а rеsіdеnce that does not mеrelу sit on the water-it belongs to it. Located within the private, gated community of The River Club on Hilton Head Island, this exceptional deep-water estate represents a rare convergence of architecture, craftsmanship, and setting, where Broad Creek becomes both your view and your playground. Arrival is marked by quiet confidence: a stone-paver driveway and arched wood entry door with copper-foil glass, set the tone. Inside, soaring ceilings, six-panel solid wood doors, crown moldings, and inlaid Chocolate Saturnia limestone establish a sense of timeless elegance. The first-floor primary suite is a true retreat, positioned to capture breathtaking water views and finished with hardwood floors. The expansive ensuite features a soaking tub, separate glass-enclosed shower, and generous custom closets. The primary suite is so substantial, it can even accommodate an in-home gym. At the heart of the home, the gourmet kitchen is designed without compromise. Custom Cuisine Laurier cabinetry, Viking and Sub-Zero appliances, dual dishwashers, Insta-Hot water, prep sink, walk-in and butler's pantries, and a dedicated wine area with Marvel cooler and Scotsman icemaker make entertaining effortless. Living spaces unfold with purpose: a formal living room anchored by a gas fireplace with limestone surround and Enkeboll carvings, a theatre room, game room with wet bar, dedicated office, craft room, and upstairs bedroom suites with custom shelving and window seats. Then there is the waterfront-unmistakable and breathtaking. Majestic live oaks frame panoramic Broad Creek views, while a custom saltwater pool and spa appear to float at river level. A covered outdoor sanctuary with a Savannah brick gas fireplace invites year-round enjoyment. For boating enthusiasts, the property stands apart. A private deep-water dock and dock house-with electricity, water, fish-cleaning station, ceiling fans, and additional floating dock-offers immediate access to the creek and beyond. The perfect spot to watch the Summertime fireworks. A new 150-foot seawall secures the shoreline. Additional highlights include a three-car garage with epoxy floors, workshop and storage, central vacuum systems, reverse-osmosis water filtration, multiple HVAC systems, and museum-quality lighting. Optional membership to the Jack Nicklaus Signature Golf Club at Indigo Run completes the lifestyle.47 River Club Drive is a legacy property.

47 River Club Drive, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

35 Ruddy Turnstone Road, Hilton Head Island
$7,650,000
CLOSED Status ⋅ 5 Beds ⋅ 7 Baths ⋅ 5,617 SqFt. ⋅ HILTONHEAD-504571 MLS
Classic oceanfront Sea Pines home at 35 Ruddy Turnstone, built by renowned Johnson Delaney Builders and thoughtfully designed by Peter Brower architect, this timeless home reflects the charm and craftsmanship of two Sea Pines legends. Note the high quality building features throughout this home such as wide stairways, high ceilings, pocket doors and all solid core doors. Full of the charm and character Sea Pines is known for, this home offers easy, comfortable coastal living with a screen porch, generous outdoor space with a pool, spa and large decking overlooking the ocean. Primary Suite with His and Her baths, Office, Eat-in-Kitchen, Living Room and Screen porch located on Second Floor allowing for awesome elevated views of pool, dunes and ocean. First floor with large welcoming foyer leading to family room with fireplace, built in book shelves, built in beverage cooler and bar sink. Three guest rooms are conveniently located on first floor, one of which opens out to the pool and ocean. You will find a fourth guest room, laundry room and an elevator stop on the mid level along with two large walk in storage closets. An elevator serves all three levels, making the home easy to enjoy for everyone. Lovingly designed and built as custom home for original owners and used only as a second home for the first 34 years. Introduced to rental market in 2025. As new oceanfront homes continue to sell in double digits, this property stands out as a chance to own and enjoy a classic Sea Pines ocean front home - full of character and ready for your vision over time.

35 Ruddy Turnstone Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - The Cottage Group, LLC. Selling Office: Sea Pines Real Estate - The Cottage Group, LLC.

12 Jessamine Place, Hilton Head Island
$5,350,000
CLOSED Status ⋅ 6 Beds ⋅ 7 Baths ⋅ 5,516 SqFt. ⋅ HILTONHEAD-504267 MLS
A 2020 custom-built luxury home just seven rows from the beach, offering exceptional privacy and golf views overlooking the 14th green of the Atlantic Dunes course in Sea Pines. Located on a quiet cul-de-sac street and centrally positioned near the Beach Club, South Beach, and Harbour Town, this home is thoughtfully designed with custom millwork, coffered ceilings, and impeccable attention to detail throughout. The residence welcomes you with a brick-arched foyer and refined main living spaces, including a living room with custom built-ins and a gas fireplace. The chef's kitchen features an oversized island ideal for entertaining, premium appliances, and a fully equipped scullery. The first-floor primary suite offers a spa-like bath with soaking tub, oversized walk-in shower, dual vanities, and a custom walk-in closet. A main-level office with a full bath and closet offers flexible use for guests or additional living space. Upstairs includes four en-suite bedrooms, one of which functions as a second primary suite, along with a spacious loft with wet-bar that doubles as a media room, and a flex space ideal for a gym or additional office. Outdoor living is a standout, with a covered porch featuring automatic screens, a gas fireplace, and a built-in grilling station. Expansive decks surround a heated and cooled saltwater infinity-edge pool with travertine decking, complemented by a fire pit and outdoor shower-all set against a private golf course backdrop. Enhanced by extensive smart-home technology, including whole-home audio, lighting and shade control, security, multi-zone HVAC, and automated pool systems. A three-car garage completes this private luxury offering, conveniently located near the beach, golf, and Sea Pines amenities.

12 Jessamine Place, Hilton Head Island

Listing courtesy of Maxey Blackstream Christie's International Real Estate. Selling Office: Howard Hanna Allen Tate Lowcountry.

53 Ribaut Drive, Hilton Head Island
$3,100,000
CLOSED Status ⋅ 4 Beds ⋅ 6 Baths ⋅ 5,696 SqFt. ⋅ HILTONHEAD-504458 MLS
Rare peninsula waterfront estate on privately gated Ribaut Island. Experience unparalleled coastal living in one of the most unique waterfront settings on Hilton Head Island. Situated at the end of a quiet cul-de-sac, the home features 4 ensuite bedrooms and 2 half baths, breathtaking direct views of the Port Royal Sound, the Intracoastal Waterway, and Pine Island. Expansive glass sliders span the back of the home, flooding the interior with natural light and creating a seamless connection to the water beyond. The main level offers an open-concept kitchen and living area with soaring cathedral cantilevered ceiling, exposed beams, a gas fireplace, pass-through wet bar, and an open loft overlooking the space. A dedicated den/office with custom built-ins provides a serene workspace with stunning water views. The main-level primary suite offers a spacious bath, walk-in closet and views of the sound. The second level includes three additional bedrooms, each with its own ensuite bath, including a secondary primary suite with a cozy fireplace, heated bathroom floors and soaking tub. Additional highlights include a walk-in cedar closet, tankless "heat-on-demand" water heater, alarm system and 2-car garage with epoxy flooring. A true boater's paradise, this property is one of only 11 homes on the island with a private dock and dedicated boat-lift space with pilings and electrical outlets already installed. After a day on the water, unwind on the expansive back deck or enjoy the outdoor hot tub/spa while watching the tides change and local wildlife pass by. Located within the prestigious Hilton Head Plantation, Ribaut Island residents enjoy exclusive access to a community pool, tennis and pickleball courts, and additional dock facilities. Whether kayaking from your private dock to Pine Island or fishing in the sound, this exceptional home offers the ultimate Lowcountry waterfront lifestyle.

53 Ribaut Drive, Hilton Head Island

Listing courtesy of Keller Williams Realty. Selling Office: The Cobb Group brokered by eXp Realty.

34 Bridgetown Road, Hilton Head Island
$2,750,000
CLOSED Status ⋅ 4 Beds ⋅ 5 Baths ⋅ 5,196 SqFt. ⋅ HILTONHEAD-504109 MLS
Beautifully light, bright, and open, this gorgeous home features designer touches throughout and is ideally situated along Wexford's 11th fairway, offering picturesque golf views. Designed for effortless entertaining, the main living spaces flow seamlessly from the open kitchen to a wet bar, cozy family area, and separate living and dining rooms. The stunning dining room features a built-in server and an adjacent butler's serving area, creating a perfect setting for hosting. The first-floor primary suite is a true retreat, featuring a private, tucked-away office - ideal for quiet work or study - custom built-ins flanking a gas fireplace, a spa-inspired bathroom with a standalone soaking tub, an oversized walk-in closet with a built-in dresser, and additional laundry hookups. Over the three-car garage, a private in-law suite offers a full kitchen, sitting area, and full bath - ideal for guests or extended family. Upstairs, two generously sized en-suite bedrooms are complemented by an additional family room or game room, providing flexible living space. Outdoors, enjoy a private pool added in 2022, surrounded by mature privacy hedges for a serene, resort-like setting, along with a cozy screened porch and an open back deck for expanded outdoor living. Additional features include a main-level laundry room, designer light fixtures throughout, beautiful oak floors, marble mosaic backsplashes, four fireplaces, and top-of-the-line Fulgor Milano appliances. Adding to the appeal, Wexford is undergoing exciting enhancements, including a new construction Harbour Center and an expanded clubhouse, both scheduled to open in spring 2026 - further elevating the community lifestyle. 2025 Primary Residence taxes = $10.881.07

34 Bridgetown Road, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Daniel Ravenel Sotheby's International Realty.

14 Bayley Point Lane, Hilton Head Island
$1,725,000
CLOSED Status ⋅ 5 Beds ⋅ 5 Baths ⋅ 5,511 SqFt. ⋅ HILTONHEAD-504017 MLS
Designed for flexible lifestyles, 14 Bayley Point offers a rare waterfront setting in one of Hilton Head Plantation's most sought-after locations with sweeping marsh to Port Royal Sound views and unforgettable Lowcountry sunsets. Filled with natural light and designed to feel peaceful, the home offers a thoughtful layout with inviting gathering spaces, comfortable privacy, and seamless indoor-outdoor living. Walls of windows capture stunning water views from nearly every room, while the updated kitchen with quartz countertops opens to warm living spaces and a spacious waterfront deck perfect for relaxing dinners, sunset drinks, or quiet mornings overlooking the water toward Dolphin Head Beach. The freshly expanded backyard enhances the home's connection to the outdoors. Luxurious yet warm and relaxed, this is a rare opportunity to enjoy waterfront Lowcountry living in a setting that balances privacy, comfort, and everyday livability within Hilton Head Plantation.

14 Bayley Point Lane, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC. Selling Office: Howard Hanna Allen Tate Lowcountry.

9 Guscio Way, Hilton Head Island
$6,800,000
ACTIVE Status ⋅ 8 Beds ⋅ 8 Baths ⋅ 5,752 SqFt. ⋅ HILTONHEAD-503643 MLS
A rare οpportunіtу to οwn а bеautіfullу updated 8-bedroom οcеanfront home in the heart of North Forest Beach. Designed to take full advantage of its exceptional setting, 9 Guscio Way offers sweeping Atlantic views, direct beach access, and multiple covered balconies spanning all three levels. The spacious, open-concept interior is ideal for gathering and entertaining, with an elevator serving each floor and a bonus room with a second kitchen providing added flexibility for guests. Outside, enjoy a private pool and spa, paved pool deck, lush landscaping, and a private boardwalk leading directly to the beach. Extensive improvements include a new roof, new HVAC systems, new Hardie siding, impact windows and doors, and more-offering the benefit of a well-cared-for oceanfront property with many major updates already completed. Equally appealing as a luxury second home or high-performing vacation rental, the property has generated exceptional rental income, with over $400,000 for 2026. All of this is just a short walk or golf cart ride from Coligny Plaza, Celebration Park, restaurants, shopping, and entertainment-combining the privacy of an oceanfront retreat with one of Hilton Head Island's most desirable and convenient beach locations.

9 Guscio Way, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

98 Toppin Drive, Hilton Head Island
$1,960,000
CLOSED Status ⋅ 5 Beds ⋅ 7 Baths ⋅ 5,475 SqFt. ⋅ HILTONHEAD-503898 MLS
A Lowcountry Masterpiece by renowned local architect in private, amenity rich Moss Creek. Today's most discerning buyers will appreciate the design, finishes and location of this updated and expanded residence sited on tidal creek with private dock & long marsh to Deepwater views. Features include soaring beamed ceilings, stone fireplace, built-ins, shiplap & millwork by master craftsmen, granite counters, wood flooring, top of the line Chef's kitchen, walls of windows to view, Bahamian shutters and heated, recently resurfaced courtyard pool. Very desirable floor plan offers island kitchen (w/breakfast bar) open to dining, huge great rm & Carolina rm with floor to ceiling windows. Excellent BR separation, private primary suite w/ dual baths & custom walk-in closets, stylish den/office, laundry rm, powder rm, 2 expansive guest suites, 2 loft areas, 2BR/2BA guest cottage and ample walk-in storage. All with stunning curb appeal, maximum privacy, panoramic 200+ degree views, majestic live oaks & mature plantings. A rare opportunity to call one of Moss Creek's signature properties... Home...

98 Toppin Drive, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Sea Pines Real Estate - The Cottage Group, LLC.

55 Wexford On The Green, Hilton Head Island
$4,295,000
ACTIVE Status ⋅ 4 Beds ⋅ 6 Baths ⋅ 5,912 SqFt. ⋅ HILTONHEAD-503338 MLS
Currently under сonstructіοn, thiѕ mοdеrn cuѕtοm townhome offers marѕh front vіews and scenic vistas of the Wexford golf course, just a short distance from the clubhouse and community pool. Thoughtfully designed for elevated Lowcountry living, the home features a chef's kitchen with custom cabinetry, premium appliances, and a dedicated scullery, opening to a spacious family room with fireplace. The primary suite is located on the first floor and includes a spa-inspired bath with custom vanity, a generous walk-in closet with direct access to the laundry room. Also on the main level are a private office and elevator access to all floors. The second floor offers an additional living room with gas fireplace and kitchenette, a second laundry room, and three ensuite guest bedrooms. A dedicated spa room provides space for a sauna and/or workout area and opens to a rooftop garden. The third floor features a versatile bonus space ideal for a media room, game room, or lounge, complete with built-ins, wet bar, fireplace, art room, and additional storage. Step outside to a private balcony with hot tub and a real wood-burning fireplace with gas starter. Additional highlights include a six-car garage with extensive walk-in storage and dedicated golf cart parking for up to three carts, spray foam insulation, tankless water heater, and modern construction throughout. Enjoy the Wexford lifestyle with a private marina on Broad Creek with a lock system, championship golf, tennis and pickleball, clubhouse dining, community pool, and a gated setting just minutes from Hilton Head Island beaches, dining, and shopping.

55 Wexford On The Green, Hilton Head Island

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

7 Lavington Road, Hilton Head Island
$2,900,000
CLOSED Status ⋅ 4 Beds ⋅ 6 Baths ⋅ 5,010 SqFt. ⋅ HILTONHEAD-503146 MLS
Welcome to a masterpiece of modern Lowcountry living. Newly completed in the prestigious, gated community of Long Cove on Hilton Head Island Custom-built by the renowned Jeffcoat Builders and impeccably curated by Kelly Caron Designs, this 4-bedroom plus study luxury residence blends timeless Lowcountry elegance with sophisticated contemporary style. From the moment you enter, you'll appreciate the thoughtful design and layout perfect for comfort and effortless entertaining. Sun-filled living spaces flow seamlessly to expansive outdoor areas that showcase the home's serene, private setting. At the heart of the home is a chef-inspired kitchen that defines upscale coastal living. Outfitted with state-of-the-art appliances, custom cabinetry, and refined finishes, this kitchen is as functional as it is stunning. A generous scullery provides additional prep space and storage-ideal for hosting and keeping the main kitchen pristine. The adjacent signature beverage bar completes the home's entertaining potential, making gatherings effortless and memorable. Step outside to your own private oasis: a beautifully landscaped backyard featuring a custom pool and spa by Year Round Pools, creating a resort-style atmosphere ideal for relaxation and enjoyment year-round. This is more than a home-it's a lifestyle of comfort, craftsmanship, and coastal sophistication. Experience unmatched quality and design in the heart of Long Cove.

7 Lavington Road, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: William Raveis - Carolina LLC.

22 Wexford On The Green, Hilton Head Island
$1,995,000
PENDING Status ⋅ 7 Beds ⋅ 8 Baths ⋅ 6,593 SqFt. ⋅ HILTONHEAD-503299 MLS
A rare οpportunіtу to οwn thе οnly tοwnhοme on the market with pаnorаmic Broad Creek views, this extraordinary 7BR, 7.5BA residence offers nearly 6,500 sq ft of impeccably crafted living space. Built by renowned Cambridge Construction and owned by only one family, the home showcases exceptional detail throughout-custom millwork, wood flooring, fireplace, and an elevator servicing all floors. Designed for grand living and effortless entertaining, the main level features an open great room/kitchen/dining concept with breathtaking water views. The dream kitchen includes premium appliances, extensive cabinetry, generous workspace, and a wet bar. Multiple verandas invite you to unwind while taking in the stunning creek vistas and coastal breezes. The first-floor owner suite provides convenience and privacy, while additional living spaces include an office, media room, a 2nd level owner's suite, and a top-level retreat perfect for kids or grandkids, complete with separate boys' and girls' bunk rooms and their own gathering area. The lower level offers a spa/hot tub overlooking Broad Creek, providing an unparalleled backdrop for relaxation. A spacious garage accommodates multiple vehicles, ideal for full-time or multigenerational living. Located near distance of everything Wexford offers, this residence enjoys access to world-class amenities: a private harbour and marina, championship Arnold Palmer Signature golf course, tennis and pickleball courts, croquet lawn, resort-style pool complex, clubhouse dining, and a vibrant year-round social calendar. Ongoing enhancements-including a 4,800 sq ft clubhouse addition, 7,300 sq ft Harbour Center, and new standalone golf shop - are scheduled for completion by April 2026. This is truly a once-in-a-lifetime offering - a stunning waterfront townhome with unmatched space, craftsmanship, and views, designed for gathering, celebrating, and creating unforgettable family memories. Purchaser to assume balance of special assessment ($9,800) over seven years.

22 Wexford On The Green, Hilton Head Island

Listing courtesy of Charter One Realty.

20 N Port Royal Drive, Hilton Head Island
$6,500,000
ACTIVE Status ⋅ 3 Beds ⋅ 5 Baths ⋅ 5,725 SqFt. ⋅ HILTONHEAD-502804 MLS
Spectacular must-see modern and dramatic Wayne Windham designed oceanfront estate in residential Port Royal. This gorgeous home offers a flexible floor plan with a gourmet kitchen and great room, 3-4 bedroom suites, and endless extra living areas to accommodate an office, children's area, game tables, piano room, work-out room, you name it! Perfect for family living as well as entertaining! Located on a prime ocean view lot, this home has been lightly lived in. Professional landscaping, free-standing columns, dramatic sweeping twin staircases, saturnia inlayed flooring, Vitricore kitchen cabinets, fireplace, glass brick walls, infinity pool, are just some of the upscale appointments of this light-filled masterpiece.

20 N Port Royal Drive, Hilton Head Island

Listing courtesy of Sea Pines Real Estate South Beach.

62 Yorkshire Drive, Hilton Head Island
$3,100,000
CLOSED Status ⋅ 4 Beds ⋅ 5 Baths ⋅ 5,493 SqFt. ⋅ HILTONHEAD-503126 MLS
Experience luxury living at its finest in this beautifully reimagined 4-bedroom residence on one of Wexford's most prized homesites. Offering over 5,490 sq ft of refined living space, this home showcases exceptional updates throughout, including a stunning chef's kitchen with custom cabinetry and top-of-the-line appliances. The main-level primary suite features a lavish spa-inspired bath with a steam room, while three additional en-suite bedrooms ensure comfort and privacy for family and guests. Designed for both everyday living and elegant entertaining, the home features formal and casual gathering spaces, including a dining room, formal living room, family room, and a light-filled Carolina room. Enjoy serene Lowcountry living from the manicured backyard, complete with a screened porch, expansive veranda, and a heated/cooled pool overlooking panoramic views of the 17th green, marsh, and Broad Creek. A rare opportunity to own a modernized estate in one of Hilton Head's premier gated communities.

62 Yorkshire Drive, Hilton Head Island

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

20 Balmoral Place, Hilton Head Island
$1,712,000
CLOSED Status ⋅ 4 Beds ⋅ 6 Baths ⋅ 5,026 SqFt. ⋅ HILTONHEAD-502495 MLS
Arguably one of the prettiest homes in the Golf Club community, 20 Balmoral offers stunning multiple golf course views and exceptional custom craftsmanship. This elegant residence features soaring ceilings in the living and dining rooms, an office with built-ins, four spacious bedrooms each with an en-suite bath, and a luxurious primary suite with a large walk-in closet and private exercise room. The chef's kitchen boasts two islands, a Thermador 6-burner gas cooktop, brand-new GE Monogram convection ovens, and a walk-in pantry. Enjoy a private heated saltwater pool, screened-in porch with an outdoor pool bath, and a 200-bottle wine cellar. Upstairs includes two bedrooms and a kitchenette. The guest suite on the rear of the home has a private balcony and panoramic views. Southeastern exposure to the golf course on one of the quietest streets in the Golf Club. Additional highlights include a new roof (2022), new appliances, and electric vehicle charger...must see to appreciate!

20 Balmoral Place, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: William Raveis - Carolina LLC.

63 Bridgetown Road, Hilton Head Island
$3,600,000
CLOSED Status ⋅ 5 Beds ⋅ 7 Baths ⋅ 7,196 SqFt. ⋅ HILTONHEAD-502080 MLS
Experience stunning harbourfront living at 63 Bridgetown Road, where sweeping views of Wexford Harbour and the Clubhouse set the stage for breathtaking sunsets and elegant Lowcountry living. Two levels of rear decks, a 70' private dock, and a private pool with a covered lanai create an unmatched setting for outdoor entertaining and relaxation.Inside, the main level offers a spacious and thoughtfully designed layout perfect for both everyday comfort and hosting guests. The home features a formal living room, a cozy family room off of the spacious kitchen, a dedicated office, and a formal dining room. The main-level primary suite is exceptionally large, showcasing beautiful harbour views, dual walk-in closets, and luxurious finishes. A powder room, convenient laundry area, and easy elevator access complete this level, blending elegance with practicality.Upstairs, you'll find the second primary suite along with two additional ensuite bedrooms. A generous game room with a bar and full bath adds to the versatility of the space - it can easily serve as a fifth bedroom, media room, or entertainment area. A second laundry room adds convenience for upper-level living.On the ground level, a finished drive-through garage offers exceptional functionality with room for four or more vehicles-a rare feature in Wexford that combines practicality with luxury.As a Wexford resident, you'll enjoy world-class amenities including a private marina, championship golf, tennis and pickleball courts, croquet, clubhouse dining, a resort-style pool complex, and a vibrant year-round social calendar. Exciting improvements are underway - an expanded Clubhouse and a brand-new Harbour Center are scheduled for completion in April 2026, enhancing Wexford's already unmatched lifestyle experience.With timeless design, versatile living spaces, and spectacular sunset views, 63 Bridgetown Road stands as a truly remarkable waterfront residence in one of Hilton Head Island's most distinguished private communities.

63 Bridgetown Road, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Luxury Homes of Hilton Head.

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