Calibogue Cay, Hilton Head Island, SC Homes for Sale

Find the newest home listings in Calibogue Cay, Hilton Head Island today! For those looking for a sense of beauty and serenity, the Calibogue Cay is a favored neighborhood. Deepwater views and miles of world famous white sandy beaches perhaps make Calibogue Cay the most exclusive residential address on Hilton Head Island. For more information on real estate for sale in Calibogue Cay, Hilton Head Island, schedule a showing, call us today or send us an email.

Gearing up to buy or sell a home soon in Hilton Head Island? Call Group DiNenna at 843-781-6700. Your neighborhood Calibogue Cay, Hilton Head Island realty team is here to help navigate the Hilton Head Island real estate market.

Calibogue Cay, Hilton Head Island Real Estate Market

In the Sea Pines Plantation area, Calibogue Cay homes feature exquisite modern construction with shingled roofs, designer shutters, attractive and manicured lawns, decorated patios, private decks, and views for days of magnolia trees, daylilies, butterfly plants, and the Japanese Clerodendrum.

Many homes in the Calibogue Cay neighborhood have undergone fresh updates, including a wet bar, fireplace, steam shower, window treatments, high ceiling entrance foyer, gourmet kitchen, and custom wine cellars. The single family homes offer 4 to 5 bedrooms, 4 to 5 bathrooms, and sizes ranging between 3,200 and 5,560 square feet.

The Calibogue Cay homes for sale typically range between $1 million and $4 million, depending on size, style, design, amenities, and finishes.

Calibogue Cay, Hilton Head Island, Neighborhood Amenities

The Calibogue Cay community is nestled among the pines beside a lagoon on 1.9 acres of land in the heart of Sea Pines Plantation. The perfect beach retreat offers miles of public pathways and nature trails on which pedestrians can enjoy the spectacularly diverse island, which includes over 24 golf courses for beginners to the seasoned golfer, waterfront access to the ocean, and many more.

Located nearby, residents are a short drive from all that Sea Pines Forest Preserve, Harbour Town Lighthouse, and South Forest Beach has to offer. On the Sea Pines Forest Preserve, discover the 4,000 year old Sea Pines Shell Ring, acres of flora blooming in the wildflower field , marshes, forests, and wildlife from a boardwalk through the vanishing swamp, or enjoy a picnic along the banks of Fish Island. Throughout Harbour Town Lighthouse, residents can enjoy walks along the waterfront, indulging in many dining and shopping options. Lastly, in South Forest Beach, also considered the main island's downtown area, residents can walk along a mile stretch of beachfront, close access to beachside barefoot cafes, Forest Beach shopping, and lively entertainment.

The Calibogue Cay community residents have easy access to the Cross Island Parkway, where they will find any daily essentials needed. From local favorites to recognized national chains, you'll find the food and beverage items you're craving at one of our many Hilton Head Island grocery shops, such as Walgreens, Publix Supermarket at Cross Island, and Enmarket.

Calibogue Cay, Hilton Head Island School Information

The Calibogue Cay community is located within a highly ranked educational district offering students education from prekindergarten through grade 12. Many of the schools within the Calibogue Cay community are award winning schools across Hilton Head's Island. Schools located near the Calibogue Cay community include:

Hilton Head Elementary School

30 School Road, Hilton Head, South Carolina

Grade 1 - Grade 5

Student Enrollment: 888

Hilton Head Christian Academy

55 Gardner Dr., Hilton Head, South Carolina

Kindergarten - Grade 12

Student Enrollment: 371

Hilton Head Middle School

55 Willborn Rd., Hilton Head, South Carolina

Grade 6 - Grade 8

Student Enrollment: 1,018

Hilton Head Heritage Academy

11 New Orleans Rd., Hilton Head, S.C.

Grade 7 - Grade 12

Student Enrollment: 125

Hilton Head High School

70 Wilborn Rd., Hilton Head, South Carolina

Grade 9 - Grade 12

Student Enrollment: 1,304

St. Francis Catholic School

45 Beach City Rd., Hilton Head, S.C.

Pre Kindergarten - Grade 8

Student Enrollment: 211

*Disclaimer: Always check with your local school district to confirm zoning, enrollment requirements and attendance eligibility.

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Homes for sale in Calibogue Cay, Hilton Head Island, SC

$4,800,000

5 Beds ⋅ 6 Baths ⋅ 5,206 SqFt. ⋅ HILTONHEAD-511968 MLS

Set on one of Sea Pines' most prestigious streets, this exceptional waterfront estate offers breathtaking views, timeless architecture, and an unmatched Lowcountry lifestyle. Featuring 5 bedrooms, 5.5 baths, a spacious bonus room, and an oversized 2-car garage, this remarkable residence was thoughtfully designed for luxurious everyday living and effortless entertaining. Perfectly positioned to capture sweeping views of Calibogue Sound and the surrounding marshes, the home seamlessly blends elegant interiors with spectacular outdoor living. Expansive windows fill the home with natural light while framing picturesque water vistas. The well-designed floor plan offers generous gathering spaces, private guest accommodations, and exceptional flow for both everyday living and entertaining. Step outside to your own private retreat featuring a sparkling pool, beautifully landscaped grounds, and a charming gazebo overlooking the water. The private deep-water dock provides direct access for boating, fishing, kayaking, and unforgettable sunset views over Calibogue Sound. With five spacious bedroom suites, a large bonus room offering flexible living space, and an oversized two-car garage, this home combines luxury, comfort, and functionality in one extraordinary package. Located within the gates of Sea Pines, residents enjoy world-class amenities including miles of pristine beaches, Harbour Town, the Sea Pines Beach Club, championship golf, tennis, leisure trails, equestrian facilities, marinas, dining, shopping, and one of the most sought-after lifestyles on Hilton Head Island. A rare opportunity to own a premier waterfront estate on one of Sea Pines' most coveted streets.

31 N Calibogue Cay Road, Hilton Head Island

Listing courtesy of Charter One Realty.

$8,700,000

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.

$4,250,000

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.

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