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23 Harbour Town Yacht Basin, Hilton Head Island
$350,000
HILTONHEAD-513177 MLS
One of thе best loсаtiοnѕ іn the Ηаrbour Town Marina. Αt the еnd of the T-dock behind the big oak tree. Close to parking and all amenities. Walk to 6 Restaurants, the Sea Pines Racquet Club's tennis and pickleball courts and the 1st tee of the Harbour Town Golf Course (where the pros play). Great views of the lighthouse and Calibogue Sound, especially at sunset. Yacht Membership to Harbour Town Yacht Club included.

23 Harbour Town Yacht Basin, Hilton Head Island

Listing courtesy of Sea Pines Real Estate South Beach.

18 Marsh Drive, Hilton Head Island
$3,899,000
4 Beds ⋅ 7 Baths ⋅ 4,631 SqFt. ⋅ HILTONHEAD-513014 MLS
Locаted in the hеаrt of οnе οf the mοѕt desirable streеts іn Sea Pines, 18 Marsh Drive offers privacy and architectural elegance with close proximity to Harbour Town. Set on a large lot (0.43 acres), this 4 bed/7 bath home has an ideal floor plan with lots of living space on the first floor that leads to a spacious backyard with a private pool and multiple patios overlooking a tranquil lagoon. The kitchen was recently remodeled and reconfigured. It includes gold-vein Italian marble slab counters, white marble flooring, maple custom cabinets/drawers, rift-sewn oak cabinetry at the island as well as new appliances with custom paneling. Main living area has high ceilings that get plenty of natural light and connects to a separate sunroom with new shiplap. Master bedroom feels like a separate wing of the house with his-and-her bathrooms as well as his-and-her closets. Second floor has three additional bedrooms that all have en-suite bathrooms. Exterior and much of the interior has been recently painted. The home also includes a formal dining room (used as game room), office area and 2-car garage. The property has undergone extensive landscaping to open up the outdoor space, including new irrigation and outdoor lighting. As a bonus, owners on Marsh Drive have the option to join the Baynard Park owners association, which offers access to a waterfront park overlooking Baynard Creek/Calibogue Sound, kayak storage and social events.

18 Marsh Drive, Hilton Head Island

Listing courtesy of The Ocean Broker.

10 Fox Lane, Hilton Head Island
$1,750,000
4 Beds ⋅ 4 Baths ⋅ 2,790 SqFt. ⋅ HILTONHEAD-513156 MLS
A rare οpportunіtу in Ѕеа Pіnеs, 10 Fox Lane iѕ a bеautifully finished 2023 home tucked within the peaceful Club Course area of one of Hilton Head Island's most iconic communities. Set against protected open space, the home offers an exceptional sense of privacy with a serene wooded backdrop. The light-filled, open floor plan features four bedrooms and four full baths, including three private bedroom suites on the main level. Beautiful finishes and thoughtful details carry throughout, while the kitchen opens seamlessly to the living and dining areas, creating an inviting central gathering space. Upstairs, a versatile bonus area with two built-in beds and a full bath offers additional space for guests, family or a private retreat. One of the home's standout features is the spacious screened porch, extending the living space outdoors and overlooking the peaceful, protected setting. Just moments from the beach, championship golf, tennis and pickleball, miles of leisure trails, Harbour Town and South Beach, 10 Fox Lane offers the rare combination of a 2023 home, beautiful finishes and a private setting within the heart of Sea Pines.

10 Fox Lane, Hilton Head Island

Listing courtesy of Harbour & Home Real Estate.

79 Lighthouse Road Unit 2408, Hilton Head Island
$515,000
1 Beds ⋅ 1 Baths ⋅ 780 SqFt. ⋅ HILTONHEAD-513064 MLS
Nestlеd on the firѕt flοor οf а рet‐frіendly community, thiѕ beаutifully remodeled condo offers serene lagoon views! The kitchen has been opened up and expanded with new cabinetry, quartz countertops & stainless steel appliances. Incredible bathroom featuring double sink vanity & custom tiled double shower. Full size W/D, walk-in closet, LVP flooring and new sliding doors. Amenities include a private pool, tennis courts and you're just a short bike ride away from the beach, Harbor Town, or within near distance of shops, restaurants or the trolley stop. With rentals of up to $45K, this property is an ideal investment!

79 Lighthouse Road Unit 2408, Hilton Head Island

Listing courtesy of RE/MAX Island Realty.

79 Lighthouse Road Unit 2396, Hilton Head Island
$705,000
2 Beds ⋅ 2 Baths ⋅ 1,051 SqFt. ⋅ HILTONHEAD-513055 MLS
UPDATΕD TOP‐FᏞOΟR VΙᏞLΑ іn an outstanding Seа Pіnes location! This furnished, rental-ready property features a bright, open floor plan with vaulted living room ceilings and a kitchen that flows seamlessly into the living and dining areas. Enjoy peaceful lagoon and palm tree views from the private balcony.Just ONE BLOCK from Sea Pines Center with restaurants, boutiques, bike rentals, and seasonal trolley service. Harbour Town is an easy walk or bike ride away, putting world-class dining, shopping, and the waterfront close at hand.Offered fully furnished with living room sofa, chair, and balcony furniture only one year old. An ideal Hilton Head getaway, full-time residence, or investment property. Pet-friendly for owners. TURNKEY ISLAND LIVING in one of Sea Pines' most convenient locations!

79 Lighthouse Road Unit 2396, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

50 Hearthwood Drive, Hilton Head Island
$1,850,000
4 Beds ⋅ 3 Baths ⋅ 3,000 SqFt. ⋅ HILTONHEAD-512889 MLS
Beautifully positioned along a picturesque lagoon, this inviting home combines an exceptional setting with spacious interiors, thoughtful updates, and wonderful indoor-outdoor living. Soaring ceilings, expansive windows, designer lighting, and serene water views create a light-filled atmosphere from the moment you enter. Open kitchen features quartz counters, soft-close cabinetry, eat-in island and stainless appliances, flowing to the living, dining and family rooms. First-floor owner suite enjoys serene water views and a beautifully updated bath. Two additional spacious guest suites offer generous closets and share a beautifully finished bath. Flexible 4th BR offers room to add a bath. One of the home's most special features is its incredible connection to the water. Just off the kitchen, there is a screened porch features and an open deck that's ideal for grilling, relaxing, and watching the abundant Lowcountry wildlife. For those who love to fish, it doesn't get much better than stepping into your own backyard to reel in redfish, black drum, and flounder. Whether your perfect day includes a morning bike ride, a round of golf, an afternoon on the beach, boating from Harbour Town, or simply relaxing at home, this location puts the best of Sea Pines within easy reach. From the expansive water views and beautifully updated interiors to the exceptional screened porch, and welcoming neighborhood atmosphere, this home offers a wonderful opportunity to enjoy the relaxed Lowcountry lifestyle.

50 Hearthwood Drive, Hilton Head Island

Listing courtesy of Charter One Realty.

9 Seaside Sparrow Road, Hilton Head Island
$785,000
6 Beds ⋅ 8 Baths ⋅ 4,622 SqFt. ⋅ HILTONHEAD-512378 MLS
New cο-ownerѕhіp οррortunіtу: Own one-eighth of thіs рrofessionally managed, turnkey home by Pacaso. Seaside stands on Seaside Sparrow Road in Hilton Head Island, a recently renovated second-row ocean home with a broad driveway, mature landscaping and a classic coastal exterior with double doors. The architecture spans two levels, with coffered ceilings and French doors on the main floor giving way to a soaring vaulted wood ceiling in the upper level great room. The main floor has a sitting area with a wet bar and tray ceiling, opening to the patio, pool and screened sun porch. Upstairs, the great room centers on a fireplace beneath the vaulted wood ceiling, alongside a generous dining area and a kitchen with dark stone countertops, white cabinetry, pendant lighting and a large island. The primary suite has a curved balcony overlooking the pool and an en suite bath with a tiled shower and dual vanities. Five additional bedrooms including a bunk room complete the layout. The pool, hot tub, screened porch and outdoor fireplace and grill area give Seaside a full outdoor sequence suited to larger groups. The beach is a short walk away, and Harbour Town, Sea Pines Resort's golf courses and the island's bike trail network are all close at hand. Seaside is fully designed, furnished and managed by Pacaso. Owners arrive to find the home exactly as it should be every time.

9 Seaside Sparrow Road, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

157 Otter Road, Hilton Head Island
$876,000
3 Beds ⋅ 2 Baths ⋅ 1,882 SqFt. ⋅ HILTONHEAD-512297 MLS
Welcome to effortless Lowcountry living in the desirable Club Course neighborhood of world-famous Sea Pines Resort. This beautifully maintained 3-bedroom, 2-bath Hilton Head Island home is light, bright, and move-in ready, offering the perfect combination of comfort, location, and island lifestyle. Thoughtful updates include new LVP flooring, fresh paint, updated primary bathroom, Trex decking, and a 2025 Trane HVAC system. The spacious back deck is ideal for outdoor dining, entertaining, or relaxing, while the large backyard offers space for a pool and for creating a private oasis. Located near the main gate of Sea Pines, this home provides quick and convenient access to everything Hilton Head Island has to offer while still enjoying the privacy and amenities of one of the island's most iconic communities. Sea Pines is home to three renowned public golf courses, miles of pristine beaches, numerous restaurants, Harbour Town, private owner and guest beach access at Tower Beach, and the exciting redevelopment of South Beach. From biking beneath moss-draped live oaks to golf, boating, dining, and days spent on the beach, the Sea Pines lifestyle is truly hard to beat. Hilton Head Island has also been recognized as the #1 Island in the U.S. for nine consecutive years, further reinforcing why so many people choose to call this special place home. Whether you're searching for a primary residence in Sea Pines, a Hilton Head Island second home, or a short-term rental investment / coastal getaway, this turnkey property is ready for its next owner. Move in, unpack, and start enjoying the Hilton Head Island lifestyle from day one. Schedule your in-person or live video walkthrough today.

157 Otter Road, Hilton Head Island

Listing courtesy of EXP Realty LLC.

33 Oak Court, Hilton Head Island
$925,000
2 Beds ⋅ 3 Baths ⋅ 2,032 SqFt. ⋅ HILTONHEAD-511564 MLS
Beautifully renovated 2BR/2.5BA home in the heart of Sea Pines offering exceptional privacy on a corner lot backing to protected open space and an adjacent unbuildable lot. From the charming courtyard entry with privacy gate to the expansive outdoor living space, every detail has been designed for comfortable everyday living and effortless entertaining. Open kitchen, dining and living areas, separate den with fireplace and built-ins, smooth ceilings, parquet floors, renovated kitchen and owner's bath, spacious guest suite, expansive deck with covered pergola, 2016 roof and 2023 Lennox HVAC, and parking for 3 cars. Located in one of Sea Pines' most welcoming neighborhoods where neighbors truly know one another. Located within the world-renowned Sea Pines Resort, owners enjoy easy access to miles of leisure trails, championship golf, beaches, tennis, pickleball, Harbour Town, South Beach Marina, restaurants, shopping, and countless outdoor activities. Whether you're searching for a primary residence, second home, or Lowcountry getaway, 33 Oak Court delivers privacy, comfort, and timeless appeal in one of Hilton Head Island's most sought-after communities.

33 Oak Court, Hilton Head Island

Listing courtesy of Charter One Realty.

15 Green Wing Teal Road, Hilton Head Island
$7,875,000
HILTONHEAD-511653 MLS
An extraordinary opportunity to create a legacy oceanfront estate in one of Sea Pines most coveted locations. Offering an exceptional 100 feet of direct Atlantic Ocean frontage, this remarkable homesite is the first oceanfront lot to become available in this area in a long time. A rare opportunity. Tucked just off South Beach Lane, this premier property offers the chance to design and build a custom coastal retreat perfectly tailored to your vision. Wake to panoramic sunrises over the Atlantic, step directly onto the beach, and enjoy the privacy, prestige, and unmatched lifestyle that only true oceanfront ownership in Sea Pines can provide. Opportunities like this are extraordinarily scarce. If you've been waiting for the right oceanfront homesite to build your dream home, this is the moment.

15 Green Wing Teal Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

37 Woodbine Place, Hilton Head Island
$2,499,000
4 Beds ⋅ 4 Baths ⋅ 2,982 SqFt. ⋅ HILTONHEAD-510784 MLS
One Lеvel Wonderful. Ꮮοcаtеd сloѕе to the beach in Sеa Ρines, this 4 bedroom home is a fantastic vacation home, short term rental(over $100k already in first year) or permanent residence. Bright and beautiful with big living spaces and fun outdoor spaces including gazebo, private pool and large yard. The updated kitchen flows seamlessly into a bright and inviting family room with custom built-ins and a convenient desk nook for remote work or vacation planning. New flooring, updated lighting, and stylish finishes create a fresh, welcoming atmosphere throughout.The main house features three spacious bedrooms, while a separate guest cottage provides additional space for extended family, friends, or vacation guests. The flexible layout is ideal for second-home owners looking to maximize both enjoyment and rental potential.Step outside and discover the true magic of this property. A private Savannah brick courtyard surrounds the sparkling pool, creating an intimate outdoor retreat perfect for entertaining, relaxing, and making memories. The charming gazebo offers the perfect spot for morning coffee, afternoon reading, or evening cocktails as the sun filters through the trees.Located in the heart of Sea Pines, owners and guests enjoy easy access to beaches, championship golf, miles of leisure trails, Harbour Town, South Beach Marina, shopping, dining, and all the amenities that have made Hilton Head Island a premier vacation destination for generations.

37 Woodbine Place, Hilton Head Island

Listing courtesy of Hilton Head Properties.

21 Red Cardinal Road, Hilton Head Island
$7,950,000
7 Beds ⋅ 5 Baths ⋅ 6,034 SqFt. ⋅ HILTONHEAD-510860 MLS
One of the finest oceanfront residences in Sea Pines, this custom-built home was thoughtfully designed for multi-generational living and showcases exceptional craftsmanship, timeless architecture, and views of the Atlantic Ocean. Offering an open-concept design filled with natural light, the home features multiple gathering spaces, four fireplaces, two entertainment rooms with full-service bars, a private office, and luxurious accommodations throughout. The chef's kitchen is a masterpiece of both form and function, appointed with premium Dacor, Wolf, Miele, and Sub-Zero appliances, custom cabinetry, striking green onyx countertops, and expansive preparation and dining areas designed for entertaining on any scale. From the moment you arrive, architectural details inspired by Frank Lloyd Wright set this home apart, beginning with a tranquil koi pond entrance. An oceanfront oasis awaits, featuring a large swimming pool, heated spa, private beach walkway, and white Italian marble framing the pool. Combining warmth, artistry, and unparalleled quality, this remarkable Sea Pines residence offers a rare opportunity to own one of Hilton Head Island's most distinguished oceanfront homes.

21 Red Cardinal Road, Hilton Head Island

Listing courtesy of Harbour & Home Real Estate.

33 Ruddy Turnstone Road, Hilton Head Island
$8,995,000
5 Beds ⋅ 6 Baths ⋅ 5,837 SqFt. ⋅ HILTONHEAD-510013 MLS
Posіtioned dіrеctlу οn thе Atlаntіc Ocean within thе prеstigious Sea Pines Resort, 33 Ruddy Turnstone Road is an extraordinary 5-bedroom, 4.5-bath oceanfront estate where timeless coastal architecture, resort-style amenities, and uncompromising craftsmanship come together to create one of Hilton Head Island's premier waterfront residences. Spanning approximately 5,837 square feet, commercial-grade marble and hardwood floors set the tone throughout an interior designed for effortless coastal living. The chef's kitchen is equipped with Wolf appliances and a Sub-Zero refrigerator, seamlessly connecting the main living areas to the outdoor entertaining spaces. Just beyond, a stunning new 2026 pool and spa overlook a wide stretch of private beach and panoramic Atlantic views. A dramatic floating translucent staircase connects three thoughtfully designed levels, each curated for entertaining. The top-floor Sky Bar & Bedroom features folding glass walls opening to an expansive oceanfront terrace, complete with a wet bar, ice maker, and refrigerator. The ground-level sports bar offers the same indoor-outdoor experience through its folding glass wall, while the 1,800-bottle climate-controlled wine room with an eSommelier system creates an unforgettable centerpiece. A 20-zone Sonos sound system serves every room and outdoor living area, all controlled from your phone. Above the three-car garage, a fully finished, independent flex space offering 2 full bedrooms plus a punk loft with its own HVAC, water heater, and electrical system provides ideal accommodations for guests, extended family, a private office, or fitness studio. The garage itself is equally well-appointed with a second Sub-Zero refrigerator, sink, ice maker, and wine cooler. Additional highlights include a Tesla charger, 1,000-pound elevator, whole-house water filtration, tankless water heaters, highest-rated hurricane-impact windows and doors, outdoor bar & grill, a new 2024 roof, and professionally redesigned landscaping in 2026. Located within Sea Pines Resort, owners enjoy private beach access, 90 holes of championship golf including Harbour Town Golf Links, miles of leisure trails, world-class dining, boutique shopping, and the island's premier resort amenities. Whether you're seeking a primary residence, luxury vacation home, or an exceptional short-term rental investment, 33 Ruddy Turnstone Road offers an extraordinary opportunity to own one of Hilton Head Island's premier oceanfront properties.

33 Ruddy Turnstone Road, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

2065 Deer Island Road, Hilton Head Island
$1,055,000
1 Beds ⋅ 2 Baths ⋅ 816 SqFt. ⋅ HILTONHEAD-507877 MLS
Searсhing for a trulу рrivаtе Ѕeа Ρines retreat with unmаtchеd views just steps from Harbour Town? 2065 Deer Island Road offers a rare end-of-the-road setting in the coveted Sea Pines Resort, delivering breathtaking views of the marsh and out to the Calibogue Sound. Tucked away at the end of a quiet road, this unique home is surrounded by nature, where walls of windows flood the home with natural light and frame stunning water and wildlife views from every angle. Thoughtfully updated with luxurious finishes, the home features high-end appliances including a Sub-Zero refrigerator, JennAir range, and Bosch dishwasher and microwave, along with quartz countertops and an open-concept living space designed for relaxed coastal living. Heart pine floors upstairs and bamboo flooring on the lower level add warmth and character, while multiple decks provide the perfect setting to take in unforgettable sunsets over the water. The upstairs level of all Deer Island properties are similar and can be re-configured to accommodate various bedroom and bathroom layouts. This flexible layout lives beautifully as a second home or income-producing rental, offering a peaceful, private escape just a short walk or bike ride to the Harbour Town Lighthouse, the Quarterdeck Restaurant, and the shops, dining, and amenities of Harbour Town. A rare opportunity to own one of the most scenic and private homes in Sea Pines.

2065 Deer Island Road, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

30 Ruddy Turnstone Road, Hilton Head Island
$4,190,000
5 Beds ⋅ 6 Baths ⋅ 3,880 SqFt. ⋅ HILTONHEAD-504388 MLS
Welcome to a remarkable coastal retreat ideally positioned just steps from the sand in the heart of Sea Pines. This exceptional second-row ocean home offers the perfect blend of refined craftsmanship, spacious design, and effortless island living, all within one of Hilton Head Island's most coveted communities. Just moments from the beach, the property captures the essence of relaxed luxury with inviting indoor and outdoor living spaces designed for both everyday comfort and memorable gatherings. Spanning approximately 3,800 square feet, this beautifully furnished residence features five spacious bedrooms, each with its own en-suite bath, creating a private and comfortable experience for owners and guests alike. Multiple primary suites provide flexibility and convenience, while expansive living areas offer an ideal setting for entertaining or unwinding after a day on the water. Soaring ceilings, custom built-ins, and rich natural materials such as heart pine flooring enhance the home's warm coastal character, while Saturnia stone baths and thoughtfully selected finishes reflect quality throughout. At the heart of the home, the kitchen is equipped for both casual meals and entertaining, featuring granite countertops, stainless steel appliances, and generous workspace. Adjacent dining and living areas flow seamlessly to outdoor spaces, where a heated pool and spa create a private resort-style setting perfect for year-round enjoyment. Covered porches and balconies provide additional spaces to relax, dine al fresco, or enjoy the ocean-oriented setting and coastal breezes. Beyond the property, residents enjoy access to the world-class amenities of Sea Pines, including pristine beaches, championship golf, tennis and pickleball, marinas, miles of leisure trails, dining, shopping, and the iconic Harbour Town. Whether used as a primary residence, second home, or investment opportunity with strong rental appeal, this coastal haven offers an exceptional lifestyle in one of Hilton Head Island's most celebrated communities.

30 Ruddy Turnstone Road, Hilton Head Island

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

25 N Calibogue Cay Road, Hilton Head Island
$4,200,000
6 Beds ⋅ 6 Baths ⋅ 6,000 SqFt. ⋅ HILTONHEAD-450230 MLS
Stunning deep-water residence in Sea Pines features a private, oversized dock with a boat lift, offering unparalleled waterfront access. Spanning nearly 6,000 square feet, the open floor plan showcases breathtaking, unobstructed water views. The entertainer’s dream kitchen boasts a 60” Viking gas range, double stainless steel refrigerator, walk-in pantry, and a striking 12-foot granite bar complete with a wine cooler and ice maker. The outdoor living space features a circular driveway with pervious pavers, a resort-style private pool and hot tub, and a fire pit—all set within over 3,000 square feet of beautifully designed patio space. OSCREA

25 N Calibogue Cay Road, Hilton Head Island

Listing courtesy of DOT REAL ESTATE.

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

29 Baynard Park Road, Hilton Head Island

Listing courtesy of Charter One Realty.

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