Hilton Head Island, South Carolina listings for sale

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$5,700,000 - Hilton Head Island, SC
34 W Beach Lagoon Drive Hilton Head Island, SC - Iconic, 2nd row West Beach Lagoon estate on over 1.5 acres! Stunning views from every room. This one-of-a-kind property has been thoughtfully restored with hints of days gone by coupled with modern updates. Meander through 200-year-old, moss draped live oak trees and enjoy golf views to the side and back, OR stroll across the street to step on the white sand of a file mile stretch of pristine Atlantic beach. Recently added resort style pool on the property makes this property its own private resort. This location is nearly impossible to duplicate on Hilton Head. With many uses, it is currently a popular vacation rental grossing 200K/yr
1961 | 4 | 6 | 2,872 sqft.
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$5,595,000 - Hilton Head Island, SC
12 Cassina Lane Hilton Head Island, SC - New to Market! Welcome to coastal luxury at its finest! This inspiring 5bdrm, 5.5 bath oceanfront home features two floors with spectacular ocean view great room, kitchen, dining space & cozy fireplace. Dine al fresco in the large screened-in porch or the poolside covered lanai. Wake to the sounds of ocean from either of two richly appointed primary suites. All bedrooms with private en suites. Lush landscaping around pool/spa area and large yard. Elevator for convenience. 3-car garage, additional parking spaces. Lots of storage. Prime location to Sea Pines & Coligny Plaza for boutique shops and restaurants. A perfect family beach house or investment home!
1999 | 5 | 6 | 3,913 sqft.
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$5,595,000 - Hilton Head Island, SC
12 Cassina Lane Hilton Head Island, SC - Welcome to coastal luxury at its finest! This inspiring 5bdrm, 5.5 bath oceanfront home features two floors with spectacular ocean view great room, kitchen, dining space & cozy fireplace. Dine al fresco in the large screened-in porch or the poolside covered lanai. Wake to the sounds of ocean from either of two richly appointed primary suites. All bedrooms with private en suites. Lush landscaping around pool/spa area and large yard. Elevator for convenience. 3-car garage, additional parking spaces. Lots of storage. Prime location to Sea Pines & Coligny Plaza for boutique shops and restaurants. A perfect family beach house or investment home!
? | 5 | 6 | 3,913 sqft.
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$5,500,000 - Hilton Head Island, SC
25 N Calibogue Cay Road Hilton Head Island, SC - 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
? | 6 | 6 | 4,146 sqft.
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$5,500,000 - Hilton Head Island, SC
3 Port Tack Hilton Head Island, SC - Live the ultimate Hilton Head lifestyle in this elegant lagoon-front estate, just minutes from the beach. Crafted for relaxed luxury, this home invites you to unwind, entertain, and savor every moment—whether dining al fresco, lounging by the pool or fireplaces, or enjoying tranquil water views from your screened living areas or private dock. Highest quality finishes and furnishings throughout offer coastal comfort with inviting spaces curated for connection and calm. Every detail, from the chef’s kitchen to the serene primary suite, enhances the experience of effortless island living. Offered fully furnished with designer touches throughout.
? | 5 | 6 | 5,560 sqft.
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$5,250,000 - Hilton Head Island, SC
9 Armada Street Hilton Head Island, SC - A must-see home, perfect for entertaining! Spacious 2nd-row, 6 BR | 6 BA | 2 HB home on Armada in Palmetto Dunes just steps from 3-miles of awarding winning beach. Freshly painted with coastal chic décor, this home has a spectacular 1st-floor featuring a chef’s eat-in kitchen, dining room, living room, wet bar off of the leisure room, powder room & sunroom. Offers a 4-stop elevator & three primary suites on the 2nd-floor. Outdoor entertainment area offers idyllic wooded view, covered lounging & dining area with wet bar and grill, & a large pool with spa. Ample parking with large driveway & garage. Short walk or bike ride to resort amenities!
? | 6 | 7 | 6,741 sqft.
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$4,995,000 - Hilton Head Island, SC
29 Baynard Park Road Hilton Head Island, SC - 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!
? | 5 | 6 | 3,742 sqft.
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$4,835,000 - Hilton Head Island, SC
58 N Sea Pines Drive Hilton Head Island, SC - Offered for the first time, this 5th-row coastal, multi-generational retreat w/golf & lagoon views will captivate the most discerning buyer who is seeking location, luxury, & privacy all w/in a 3 min walk to the Sea Pines sun-kissed beaches. Enjoy 1st & 2nd floor owner suites, two family living spaces + a private upper deck, perfect for sunning or stargazing! The custom millwork, coffered ceilings, two fireplaces, gourmet kitchen w/double islands, an office or 6th BD plus a 3-car garage make this an exceptional home. All topped off by a spacious screened porch to enjoy evening breezes overlooking the resort-style pool, spa & lush landscaping.
? | 5 | 6 | 6,631 sqft.
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$4,750,000 - Hilton Head Island, SC
12 Port Tack Hilton Head Island, SC - Your Absolute Dream Awaits! Step inside this stunning,*recently renovated* (details under documents)luxury masterpiece nestled in an exclusive *beachside gated community*. This *Goliath-sized, breathtaking home* isn't just a place to live — it's a lifestyle and a lucrative investment, generating *consistent short-term rental income* Enjoy a very short walk to the beach, one of your many private terraces overlooking your private heated pool or the golf course, and evenings spent entertaining in exquisite designer spaces. Every detail has been crafted to perfection, making this an *incredibly rare, most sizable opportunity* to own a true coastal paradise. Modern amenities Expansive open floor plan Steps from pristine beaches Secure, private & gated Proven rental revenue stream Your chance has arrived to own a slice of heaven that pays for itself. Don't miss out  **act now** and make this dream home your reality!Community/home video available upon request/opportunity. (Open for showings 6/1-6/7- agent accompanied-no renters)
2004 | 6 | 6 | 7,320 sqft.
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$4,750,000 - Hilton Head Island, SC
12 Port Tack Hilton Head Island, SC - Your Dream Awaits inside this stunning, renovated (details under documents), luxury masterpiece nestled in an exclusive beachside gated community. This Goliath-sized, breathtaking home is a place to live, a lifestyle, and a lucrative STR investment. Enjoy a very short walk to the beach, one of your many private terraces overlooking your private heated pool or the golf course, and evenings spent entertaining in exquisite designer spaces. Modern amenities, Expansive floor plan, peaceful, private & gated, & a proven rental revenue stream. Your chance has arrived to own a slice of heaven that could pay for itself. Community/home video available.
? | 6 | 6 | 7,320 sqft.