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59 N Calibogue Cay Road, Hilton Head Island
$7,800,000
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.

239 Jonesville Road, Hilton Head Island
$1,350,000
4 Beds ⋅ 4 Baths ⋅ 2,774 SqFt. ⋅ HILTONHEAD-505628 MLS
Deepwater tidal dock with long marsh views! Phenomenal newer-style home offering 4 bedrooms and 3.5 baths on a spacious and very private 0.7-acre lot with no POA. Private dock with a 5,000 lb boat lift and Brazilian hardwood, perfect for enjoying boating and waterfront living. The home features a drive-under 2-car garage with approximately 1,500 square feet of storage beneath the home and a large deck overlooking the marsh. Interior highlights include red oak hardwood floors throughout, custom primary closet built-ins, a separate dining room, and fireplace. The primary suite is located on the first floor and features a double vanity, soaking tub, and separate shower. The kitchen includes quartz countertops and stainless steel appliances. Three additional bedrooms are located upstairs. New roof installed in 2024. Enjoy a private setting with expansive marsh views and the feel of country living on Hilton Head Island.

239 Jonesville Road, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Southern Lifestyle Properties of SC LLC.

1 Bridgetown Road, Hilton Head Island
$4,200,000
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.

21 N Calibogue Cay Road, Hilton Head Island
$3,750,000
3 Beds ⋅ 3 Baths ⋅ 2,549 SqFt. ⋅ HILTONHEAD-504606 MLS
Located in Sea Pines, this one-level 3 bed 2 1/2 bath waterfront home offers a deep-water dock and a private, oak-framed setting with serene water views. Vaulted, beamed ceilings, warm wood paneling, and hardwood floors create a timeless Lowcountry feel. The home features a built-in wet bar, kitchen with breakfast area, formal dining room with adjacent flex space, and a spacious primary suite with access to outdoor living. Recently remodeled with new Pella doors and expansive windows, the raised Old Savannah brick patio overlooks a lush, manicured lawn. This property sits close to the popular Harbour Town as well as beaches, golf, and leisure trails.

21 N Calibogue Cay Road, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty. Selling Office: ELEVE PROPERTIES Brokered by EXP Realty.

17 Arthur Hills Court, Hilton Head Island
$2,600,000
5 Beds ⋅ 5 Baths ⋅ 3,600 SqFt. ⋅ HILTONHEAD-509916 MLS
Private dock on Leamington's 11-Mile Lagoon. A rare opportunity to own a waterfront property in Leamington, Hilton Head Island's premier private oceanfront community. Tucked away on a quiet cul-de-sac, this 5-bedroom or 4-bedroom-plus-office residence offers expansive lagoon views, exceptional privacy, and room for a pool.Designed for both everyday living and entertainment, the home features generous living spaces, hardwood flooring in the main living areas, abundant natural light, a fireplace, a wet bar, a screened porch, and a flexible floor plan. The kitchen offers ample counter space, an island with bar seating, and views of the surrounding landscape. Whether enjoyed as-is or transformed into a custom waterfront retreat, the possibilities are endless.Enjoy kayaking, fishing, wildlife watching, and peaceful evenings from your private dock overlooking the renowned 11-Mile Lagoon. Leamington residents enjoy private beach access, an oceanfront Beach Club, championship golf, world-class tennis and pickleball, miles of leisure trails, and all the amenities of Palmetto Dunes Oceanfront Resort. Unlike many Hilton Head communities, Leamington does not permit short-term rentals, preserving its exclusive residential character and tranquility.Private Dock. 11-Mile Lagoon Views. Private Beach Access. No Short-Term Rentals. OSCREA

17 Arthur Hills Court, Hilton Head Island

Listing courtesy of Engel & Volkers. Selling Office: Premium Properties of Hilton Head.

22 Blue Heron Point, Hilton Head Island
$1,635,000
4 Beds ⋅ 4 Baths ⋅ 3,064 SqFt. ⋅ HILTONHEAD-505652 MLS
Step into a lifestyle of effortless luxury and outdoor adventure on this sprawling .573-acre estate. This backyard oasis is built for hosting, featuring a private dock with boat lift, a sparkling pool, and an outdoor fireplace-with plenty of room left for your dream outdoor kitchen and bar. Enjoy years of worry-free living thanks to the low-maintenance metal roof and cement board siding. Inside, the spacious floor plan centers around a chef's kitchen with brand new counter tops and a large dining area. The layout offers the perfect balance of retreat and togetherness, with a massive Carolina Room off the primary suite and a separate upstairs living area for guests. Complete with a three-car garage and no HOA fees, this rare gem truly has it all.

22 Blue Heron Point, Hilton Head Island

Listing courtesy of Keller Williams Realty. Selling Office: Dunes Real Estate.

15 Promontory Court, Hilton Head Island
$1,675,000
4 Beds ⋅ 4 Baths ⋅ 2,506 SqFt. ⋅ HILTONHEAD-508192 MLS
Located on the prestigious 11-mile lagoon in Palmetto Dunes, this exceptional property offers sweeping long-range views of the George Fazio Golf Course-a setting that is simply unmatched. This rare and hard-to-find lot is beautifully landscaped, creating a move-in-ready coastal retreat. Featuring 4 bedrooms and 4 full bathrooms, this home is perfect as a second residence or a high-performing investment property. Come see the updated kitchen with custom cabinets, granite and high-end stainless appliances. Palmetto Dunes is one of the island's most sought-after residential and investment communities, known for its world-class amenities and strong rental demand. Relax and take in the stunning lagoon and golf course views from your private pool-an ideal setting for enjoying the Lowcountry lifestyle. This opportunity will not last-start living your dream today!

15 Promontory Court, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC. Selling Office: Schembra Real Estate Group.

11 N Calibogue Cay Road, Hilton Head Island
$5,480,000
5 Beds ⋅ 7 Baths ⋅ 6,473 SqFt. ⋅ HILTONHEAD-441743 MLS
This spectacular 5-bedroom, 5.5-bathroom waterfront home offers unparalleled, deep water views of the Calibogue Sound, situated in the highly coveted location of Calibogue Cay within Sea Pines. Boasting 100 feet of private waterfront and built by Cambridge Builders in 2010, the home showcases exquisite craftsmanship and attention to detail, making it a premier choice for those seeking the epitome of luxury living.

11 N Calibogue Cay Road, Hilton Head Island

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

16 Full Sweep, Hilton Head Island
$3,000,000
5 Beds ⋅ 5 Baths ⋅ 4,365 SqFt. ⋅ HILTONHEAD-507812 MLS
16 Full Sweep | Lagoon Front/Private Dock, Ocean-Oriented in the Heart of Palmetto Dunes! Perfectly positioned along the lagoon with a private dock, this striking contemporary home delivers a refined take on Coastal Living. Designed by a noted architect, the residence balances bold modern lines with warmth and livability, creating an immediate Sense of Arrival! A Dramatic Entry Unfolds through Expansive Bifold Glass/Wood doors at both the front and rear, allowing ocean and lagoon breezes to flow freely through the Entryway! Inside, soaring ceilings, walls of glass, and a stunning two-story Water Wall feature set a memorable arrival! The open layout is both impressive and comfortable, designed for effortless everyday living. At the center, the chef's kitchen with Breathtaking Views, pairs function with sleek design, featuring premium Wolf and Sub-Zero appliances, Italian Snaidero Cherry Cabinetry, and Refined finishes throughout. Thoughtful details-including a discreetly integrated powder room and seamless hidden Cabinetry-maintain a clean, Architectural Aesthetic while maximizing usability. With Cherry Hardwood and Newly Refinished Sandstone Flooring throughout, Natural light fills the main living spaces, where floor-to-ceiling windows frame tranquil lagoon views stretching toward the oceanfront hole of the renowned Robert Trent Jones Golf Course! Multiple gathering areas-including a sunken living room, intimate seating spaces, and a well-appointed wet bar with Seating-offer flexibility for entertaining or relaxing by the fire. The owner's suite provides a Private Retreat with its own fireplace and elevated deck overlooking the Lagoon, Lagoon, & Golf Course! Guest accommodations are generously sized, including a flexible room ideal for a home office, private suite, or multi-generational living. Dual laundry areas, abundant storage, a two-car garage, and an electric vehicle charging station add everyday convenience. Outdoor Living is equally compelling. A Covered Loggia opens to a newly refinished Brazilian Hardwood Sundeck, complete with a heated infinity-edge pool and spa overlooking the lagoon. The private dock offers direct access for boating, kayaking, or fishing, while the Beach is just a short walk/bike ride away. Blending architectural distinction, resort-style amenities, and an exceptional location, this is a rare opportunity to own a home that is as functional as it is unforgettable. This property has Incredible Rental Potential As Well!!

16 Full Sweep, Hilton Head Island

Listing courtesy of Daniel Ravenel Sotheby's International Realty. Selling Office: Harbour & Home Real Estate.

41 Swing About, Hilton Head Island
$1,300,000
4 Beds ⋅ 3 Baths ⋅ 2,310 SqFt. ⋅ HILTONHEAD-504368 MLS
Hard-to-find waterfront in Palmetto Dunes. Set on an impressive half-acre of high land and bordered by open space to the north, this single-level four-bedroom home offers a level of privacy that's increasingly rare. A private dock along the community's renowned 11-mile lagoon system creates a unique opportunity to launch a kayak or small boat directly from your backyard. Inside, the home lives large and comfortable with tall smooth ceilings, a spacious eat-in kitchen, and a living room highlighted by exposed beams and a fireplace crowned with a beautifully crafted, old Savannah mantel. Thoughtfully insulated and exceptionally quiet, the home also features a recently installed HVAC system and water heater. A large double garage with workshop and an unfinished loft above provides flexibility and future potential. Never used as a rental and offered mostly furnished, this is a near turn-key Palmetto Dunes retreat-just a short bike ride or trolley ride to the beach.

41 Swing About, Hilton Head Island

Listing courtesy of Collins Group Realty. Selling Office: REsides, Inc..

8 Queens Way, Hilton Head Island
$1,900,000
4 Beds ⋅ 5 Baths ⋅ 4,164 SqFt. ⋅ HILTONHEAD-503491 MLS
Perfectly positioned along a tranquil lagoon and directly across from the Arthur Hills Course, this elegant residence offers a rare blend of privacy, comfort, and classic Lowcountry charm within the prestigious Leamington community. The 4-bedroom, 4.5-bath home features exceptional bedroom separation, ideal for hosting family and guests while preserving personal privacy. The inviting living room is centered around a beautiful fireplace, creating a warm and welcoming retreat with serene lagoon views. A spacious, suite-style room above the garage provides versatile space-perfect for guests, extended family, or a private home office. As one of the most sought-after neighborhoods, Leamington offers residents exclusive access to a private oceanfront beach pavilion, along with convenient proximity to golf, marina access, dining, and shopping within Palmetto Dunes.

8 Queens Way, Hilton Head Island

Listing courtesy of Peirce Group Brokered by EXP Realty LLC. Selling Office: Howard Hanna Allen Tate Lowcountry.

50 N Calibogue Cay Road, Hilton Head Island
$3,300,000
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.

35 Saint George Road, Hilton Head Island
$2,050,000
4 Beds ⋅ 5 Baths ⋅ 3,000 SqFt. ⋅ HILTONHEAD-506550 MLS
A rare opportunity to experience the full island lifestyle. This exceptional residence is a distinctive and private retreat within Palmetto Dunes, one of Hilton Head Island's most sought-after oceanfront communities. Perfectly positioned for privacy and designed to reflect the very best of island living. Set along the scenic 11-mile lagoon and situated just moments from the beach (with access conveniently next door), the location feels both tucked away and connected. The outdoor experience is nothing short of spectacular. A beautifully designed pool, framed by natural stone accents and cascading waterfalls, creates a resort-style setting complemented by expansive entertaining areas, multiple seating spaces, a screened porch overlooking the lagoon, and a private dock complete with a rare boat lift and 17' electric Carolina Skiff. Inside, the home is equally impressive. Light pours through the space, highlighting soaring ceilings, and a dramatic upper-level overlook spans both the main living area and foyer. Dual living spaces are anchored by a striking double-sided fireplace. The kitchen is crisp and thoughtfully updated, featuring a clean white aesthetic, generous pantry, and a functional connection to outdoor areas. Each bedroom is designed as a private retreat with its own en-suite bath, while the first-floor primary suite offers convenience and quiet separation. From the oversized porches and lagoon views to the private pool, dock, and beach access, every detail has been considered. A truly one of a kind offering, where privacy, location, and lifestyle converge in a way that is rarely found.

35 Saint George Road, Hilton Head Island

Listing courtesy of Charter One Realty. Selling Office: Greenplate Group Brokered by eXp Realty.

191 Mooring Buoy, Hilton Head Island
$2,050,000
4 Beds ⋅ 6 Baths ⋅ 3,248 SqFt. ⋅ HILTONHEAD-502838 MLS
Discover elegant coastal living in this ocean oriented 4-bedroom, 4 full & 2 half bath home in Palmetto Dunes. Designed with a bright, open layout and refined finishes, this property blends modern luxury with relaxed beach lifestyle. The gourmet kitchen, spacious living areas, and private bedroom suites offer comfort and style throughout. Step outside to a beautiful pool area overlooking the 11-mile lagoon, complete with your own private dock-perfect for kayaking, fishing, or simply enjoying the view. A short walk to world-class beaches, golf, and resort amenities. This home captures the very best of Palmetto Dunes living.

191 Mooring Buoy, Hilton Head Island

Listing courtesy of RE/MAX Island Realty. Selling Office: Keller Williams Realty.

53 Ribaut Drive, Hilton Head Island
$3,100,000
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.

40 Wexford On The Green, Hilton Head Island
$2,499,000
4 Beds ⋅ 4 Baths ⋅ 4,377 SqFt. ⋅ HILTONHEAD-505102 MLS
Waterfront Elegance with Sweeping Broad CreekViews! Perfectly positioned along the shimmering banks of Broad Creek, 40 Wexford on the Green captures the essence of Lowcountry luxury with timeless Charleston-inspired architecture and unforgettable water views from nearly every vantage point. A gracious side porch entry welcomes you to the front door, setting the tone for the warmth and charm that unfolds within.Designed to celebrate its remarkable setting, this home features four inviting porches-two capturing sweeping views of Broad Creek, and two overlooking the picturesque streetscape framed by majestic, moss-draped oak trees. The expansive primary suite is a true sanctuary, featuring a spacious bath, screened porch and panoramic views that greet you each morning with the beauty of Broad Creek.Indoor and outdoor living blend seamlessly. The lower-level covered entertaining space flows effortlessly onto a brick patio anchored by a built-in gas fire pit, creating the perfect backdrop for evenings with friends, family gatherings, or quiet nights under the stars. An elevator provides convenient access, ensuring comfort and ease throughout.For boating enthusiasts, a 45-foot boat slip is available in the Wexford Harbour, offering direct access to the Intracoastal Waterway and beyond.Located just moments from the heart of Wexford, residents enjoy world-class amenities including the private harbour and lock system, new Harbour Center with cafe, new Clubhouse with fine dining and a casual pub, Arnold Palmer Signature golf course, tennis and pickleball courts, croquet, swimming pools with pool bar, and a vibrant year-round social calendar. This is more than a home. It is a waterfront lifestyle defined by beauty, connection, and effortless coastal living.

40 Wexford On The Green, Hilton Head Island

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

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