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Calibogue Cay, Hilton Head Island Real Estate

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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

59 N Calibogue Cay Road, Hilton Head Island image
59 N Calibogue Cay Road, Hilton Head Island $8,700,000

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 de...

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  • 5 Beds
  • 6 Baths
  • 5,580 SqFt.
  • HILTONHEAD-508090 MLS
Courtesy of Sea Pines Real Estate - The Cottage Group, LLC

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

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21 N Calibogue Cay Road, Hilton Head Island image
21 N Calibogue Cay Road, Hilton Head Island $3,999,999

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 ...

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  • 3 Beds
  • 3 Baths
  • 2,549 SqFt.
  • HILTONHEAD-504606 MLS
Courtesy of Daniel Ravenel Sotheby's International Realty

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

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25 N Calibogue Cay Road, Hilton Head Island image
25 N Calibogue Cay Road, Hilton Head Island $4,250,000 ▼

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...

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  • 6 Beds
  • 6 Baths
  • 6,000 SqFt.
  • HILTONHEAD-450230 MLS
Courtesy of DOT REAL ESTATE

Listing courtesy of DOT REAL ESTATE.

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We do not attempt to independently verify the currency, completeness, accuracy or authenticity of the data contained herein. It may be subject to transcription and transmission errors. Accordingly, the data is provided on an “as is” “as available” basis only and may not reflect all real estate activity in the market. © 2026 REsides, Inc. All rights reserved. Certain information contained herein is derived from information, which is the licensed property of, and copyrighted by, REsides, Inc.

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HiltonHeadRealtySales.com / Group DiNenna:

Dino DiNenna
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Southern Lifestyle Properties
PO Box 7725
Hilton Head Island, SC 29938-7725
843.560.9310 Direct
843.781.6700 Team

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Southern Lifestyle Properties of SC, LLC
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5846 Guilford Place
Bluffton, SC 29910
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