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Featured Properties From Hilton Head’s Original Oceanfront Real Estate Experts

Curated by The Ocean Broker team, this featured property list exemplifies the lifestyle, location, and long-term value that define Hilton Head’s most sought-after real estate. With decades of hands-on oceanfront expertise, our team provides insight beyond the basics — helping you understand not just the property but the lifestyle, market, and investment potential behind it.

Our agents bring the wisdom and perspective of five decades of navigating Hilton Head Island's real estate market. In 1977, we sold the first building lot on the Island for $100,000. In 2006, we achieved the Island's highest-ever residential sale at $9,200,000 for a Sea Pines' oceanfront property on Surf Scoter Road. Today, we remain focused on what we know best: oceanfront and deep-water properties, where our decades of experience deliver results other brokerages can't match. We're proud to pair personalized service with the market expertise that comes from over 50 years as Hilton Head's original oceanfront experts.

Contact us today to discover how our local knowledge can serve your real estate goals.

Featured Properties

5 Sailwing Lane, Hilton Head Island image
5 Sailwing Lane, Hilton Head Island $2,550,000

Experience the best of Hilton Head Island waterfront living at 5 Sailwing Lane, a spacious harbour-front townhome in the coveted Windmill Harbour community. Offering ove...

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  • 4 Beds
  • 5 Baths
  • 3,710 SqFt.
  • HILTONHEAD-512736 MLS
Courtesy of Charter One Realty

Listing courtesy of Charter One Realty.

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91 Singleton Beach Road, Hilton Head Island image
91 Singleton Beach Road, Hilton Head Island $2,195,000

Just 100 yards from the Atlantic Ocean, this 4-bedroom, 4.5-bath Singleton Beach home offers an exceptional combination of beach proximity, beautiful marsh views, and rel...

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  • 4 Beds
  • 5 Baths
  • 2,930 SqFt.
  • HILTONHEAD-512616 MLS
Courtesy of Daniel Ravenel Sotheby's International Realty

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

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15 Peninsula Drive, Hilton Head Island image
15 Peninsula Drive, Hilton Head Island $1,395,000

Fabulous Opportunity in Moss Creek Awaits! This custom built, one-owner, 4 bedroom/4.5 bath home with office boasts never ending panoramic marsh and sunset views situate...

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  • 4 Beds
  • 5 Baths
  • 4,200 SqFt.
  • HILTONHEAD-512634 MLS
Courtesy of Dunes Real Estate

Listing courtesy of Dunes Real Estate.

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41 Ocean Lane Unit 6501, Hilton Head Island image
41 Ocean Lane Unit 6501, Hilton Head Island $3,195,000

Experience elevated oceanfront living from this stunning 3-bedroom, 3-bath Hampton Place penthouse, where breathtaking direct ocean views can be enjoyed from every balcon...

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  • 3 Beds
  • 3 Baths
  • 1,777 SqFt.
  • HILTONHEAD-512346 MLS
Courtesy of Family Tides Real Estate LLC

Listing courtesy of Family Tides Real Estate LLC.

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13 Ocean N Point, Hilton Head Island image
13 Ocean N Point, Hilton Head Island $3,195,000 ▼

Oceanfront living takes center stage at this inviting residence in Ocean Point, a private section of the prestigious Port Royal community on Hilton Head Island. Set along...

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  • 4 Beds
  • 4 Baths
  • 3,300 SqFt.
  • HILTONHEAD-511945 MLS
Courtesy of Charter One Realty

Listing courtesy of Charter One Realty.

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20 Castlebridge Court, Hilton Head Island image
20 Castlebridge Court, Hilton Head Island $3,995,000

Waterfront living in Wexford doesn't get much better than this and 20 Castlebridge Court offers the ONLY harborfront setting currently available in the community. Set di...

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  • 5 Beds
  • 7 Baths
  • 4,566 SqFt.
  • HILTONHEAD-512060 MLS
Courtesy of Daniel Ravenel Sotheby's International Realty

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

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6 Drayton Place, Hilton Head Island image
6 Drayton Place, Hilton Head Island $2,750,000 ▼

Welcome to a truly special island retreat in prestigious Port Royal on Hilton Head Island. This 4-bedroom, 3-full-bath, 2-half-bath West Indies-inspired home captures the...

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  • 4 Beds
  • 5 Baths
  • 4,075 SqFt.
  • HILTONHEAD-512097 MLS
Courtesy of Engel & Volkers

Listing courtesy of Engel & Volkers.

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2 Wexford On The Green, Hilton Head Island image
2 Wexford On The Green, Hilton Head Island $2,995,000

Rare opportunity to own one of Wexford's most distinctive residences, perfectly situated on an oversized corner double lot with picturesque harbor and Broad Creek water v...

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  • 4 Beds
  • 6 Baths
  • 6,366 SqFt.
  • HILTONHEAD-511890 MLS
Courtesy of BESTNEST By Beverly Serral

Listing courtesy of BESTNEST By Beverly Serral.

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77 Ocean Lane Unit 113, Hilton Head Island image
77 Ocean Lane Unit 113, Hilton Head Island $1,890,000

Located in the heart of Hilton Head Island, inside Palmetto Dunes Resort and across from the Shelter Cove Area. Experience the best of Hilton Head Island at 113 Barringt...

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  • 3 Beds
  • 3 Baths
  • 1,520 SqFt.
  • HILTONHEAD-511734 MLS
Courtesy of Schembra Real Estate Group

Listing courtesy of Schembra Real Estate Group.

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4 Village North Drive Unit 43, Hilton Head Island image
4 Village North Drive Unit 43, Hilton Head Island $1,595,000 ▼

Extremely rare opportunity! No expense spared in this 100% remodeled luxury penthouse villa with sweeping Skull Creek & ICW views. Top of the line, curated finishes by aw...

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  • 4 Beds
  • 4 Baths
  • 3,374 SqFt.
  • HILTONHEAD-511697 MLS
Courtesy of Charter One Realty

Listing courtesy of Charter One Realty.

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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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the ocean broker

Hilton Head Island Real Estate

843.785.7215

markdevers@theoceanbroker.com

2 Corpus Christi Place, Ste. 200
Hilton Head Island, SC 29928

   

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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. © 2019 Multiple Listing Service of Hilton Head Island, Inc. All rights reserved. Certain information contained herein is derived from information which is the licensed property of, and copyrighted by, Multiple Listing Service of Hilton Head Island, Inc. Web design by Blue Dream Creative.

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