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Hilton Head Island, SC 5 Bedroom Homes

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Hilton Head Island, SC 5 Bedroom Homes for Sale

View every 5 bedroom home for sale in Hilton Head Island, SC below. Sign up to create an account to receive new property email alerts, price change alerts, track your favorite properties & more!

If you like a 5 bedroom home in Hilton Head Island you can add it to your favorites, request more information or set up a showing.

Gearing up to buy or sell a 5 bedroom home soon in Hilton Head Island? Call Group DiNenna at 843-781-6700. Your Hilton Head Island realty team is here to help navigate the Hilton Head Island real estate market.

5 Bedroom Homes for sale in Hilton Head Island, SC

124 Sandcastle Court, Hilton Head Island image
124 Sandcastle Court, Hilton Head Island $1,699,000

Sandcastles by the Sea is a gated community gem centrally located mid-island and a 5-min walk (by direct bike path) to one of Hilton Head Island's most desired public bea...

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  • 5 Beds
  • 4 Baths
  • 3,920 SqFt.
  • HILTONHEAD-511679 MLS
Courtesy of Beach House Boutique

Listing courtesy of Beach House Boutique.

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10 Bald Eagle Road, Hilton Head Island image
10 Bald Eagle Road, Hilton Head Island $5,900,000

Properties of this caliber are increasingly difficult to find in Sea Pines. 7 Bedroom/6.5 Baths PLUS Pool Bath, 2022 construction, designer furnished and just a 3-minute ...

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  • 7 Beds
  • 8 Baths
  • 5,203 SqFt.
  • HILTONHEAD-511606 MLS
Courtesy of Sea Pines Real Estate - Beach Club

Listing courtesy of Sea Pines Real Estate - Beach Club.

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90 Sandcastle Court, Hilton Head Island image
90 Sandcastle Court, Hilton Head Island $1,695,000

Welcome to 90 Sandcastle Court, a spacious, beautifully appointed beach home in the gated Sandcastles by the Sea community. One of the larger homes in the neighborhood, t...

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  • 5 Beds
  • 6 Baths
  • 4,165 SqFt.
  • HILTONHEAD-511552 MLS
Courtesy of Daniel Ravenel Sotheby's International Realty

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

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164 Mooring Buoy, Hilton Head Island image
164 Mooring Buoy, Hilton Head Island $3,499,995 ▲

Welcome to 164 Mooring Buoy-where timeless coastal elegance meets one of Palmetto Dunes' most coveted beachside locations. Perfectly positioned on the second row with dir...

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  • 5 Beds
  • 6 Baths
  • 3,680 SqFt.
  • HILTONHEAD-511517 MLS
Courtesy of Charter One Realty

Listing courtesy of Charter One Realty.

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14 Field Sparrow Road, Hilton Head Island image
14 Field Sparrow Road, Hilton Head Island $1,250,000

Private Golf Course Estate with Guest House, Bonus Suite & Climate-Controlled Workshop - Nestled within the highly sought-after community of Hilton Head Plantation, this ...

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  • 5 Beds
  • 6 Baths
  • 4,083 SqFt.
  • HILTONHEAD-511235 MLS
Courtesy of COAST PROFESSIONALS Brokered by EXP Realty

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

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24 Rum Row, Hilton Head Island image
24 Rum Row, Hilton Head Island $3,450,000

Built in 2018 by May River Custom Homes, 24 Rum Row delivers luxury coastal living in a coveted Palmetto Dunes location, where high-end construction is notably enhanced w...

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  • 5 Beds
  • 5 Baths
  • 4,240 SqFt.
  • HILTONHEAD-511130 MLS
Courtesy of Collins Group Realty

Listing courtesy of Collins Group Realty.

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10 Collier Beach Road, Hilton Head Island image
10 Collier Beach Road, Hilton Head Island $6,295,000

Experience the pinnacle of oceanfront luxury with endless, unobstructed views of the Atlantic Ocean from this spectacular beachfront retreat on Singleton Beach. Perfectly...

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  • 6 Beds
  • 8 Baths
  • 4,247 SqFt.
  • HILTONHEAD-510633 MLS
Courtesy of Berkshire Hathaway HomeServices Hilton Head Bluffton Realty

Listing courtesy of Berkshire Hathaway HomeServices Hilton Head Bluffton Realty.

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9 Man O War, Hilton Head Island image
9 Man O War, Hilton Head Island $8,100,000

Positioned along one of Hilton Head Island's most coveted stretches of coastline, 9 Man O War presents a rare opportunity to own an exceptional beachfront home. Built by ...

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  • 7 Beds
  • 8 Baths
  • 5,800 SqFt.
  • HILTONHEAD-511151 MLS
Courtesy of Dunes Real Estate

Listing courtesy of Dunes Real Estate.

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21 Paddocks Boulevard, Hilton Head Island image
21 Paddocks Boulevard, Hilton Head Island $1,330,000 ▼

Located in the sought-after Paddocks community on Hilton Head Island, this beautifully designed five-bedroom, five-bath residence offers refined coastal living with a lig...

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  • 5 Beds
  • 5 Baths
  • 3,594 SqFt.
  • HILTONHEAD-510858 MLS
Courtesy of Daniel Ravenel Sotheby's International Realty

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

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14 Castlebridge Court, Hilton Head Island image
14 Castlebridge Court, Hilton Head Island $4,500,000

Welcome to 14 Castlebridge Court, a spectacular waterfront residence transformed into a modern masterpiece. Recently remodeled with exceptional craftsmanship and designer...

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  • 5 Beds
  • 5 Baths
  • 4,796 SqFt.
  • HILTONHEAD-511088 MLS
Courtesy of Charter One Realty

Listing courtesy of Charter One Realty.

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34 Hammock Breeze Way, Hilton Head Island image
34 Hammock Breeze Way, Hilton Head Island $2,850,000 ▼

Welcome to your dream coastal retreat on Hilton Head Island. Nestled in the highly sought-after Hammock Breeze community, this stunning like-new waterfront home offers an...

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  • 5 Beds
  • 5 Baths
  • 3,220 SqFt.
  • HILTONHEAD-510715 MLS
Courtesy of Howard Hanna Allen Tate Lowcountry

Listing courtesy of Howard Hanna Allen Tate Lowcountry.

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21 Red Cardinal Road, Hilton Head Island image
21 Red Cardinal Road, Hilton Head Island $7,950,000

One of the finest oceanfront residences in Sea Pines, this custom-built home was thoughtfully designed for multi-generational living and showcases exceptional craftsmansh...

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  • 7 Beds
  • 5 Baths
  • 6,034 SqFt.
  • HILTONHEAD-510860 MLS
Courtesy of Harbour & Home Real Estate

Listing courtesy of Harbour & Home Real Estate.

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10 Wexford Drive, Hilton Head Island image
10 Wexford Drive, Hilton Head Island $3,995,000

Welcome to 10 Wexford Drive, an extraordinary custom-built home completed in 2023, showcasing the very best of luxury living in Wexford. Thoughtfully designed with impecc...

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  • 6 Beds
  • 8 Baths
  • 5,513 SqFt.
  • HILTONHEAD-510828 MLS
Courtesy of Charter One Realty

Listing courtesy of Charter One Realty.

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17 Arthur Hills Court, Hilton Head Island image
17 Arthur Hills Court, Hilton Head Island $2,550,000

Private dock on Leamington's 11-Mile Lagoon. A rare opportunity to own a waterfront property in Leamington, Hilton Head Island's premier private oceanfront community. Tuc...

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  • 5 Beds
  • 5 Baths
  • 3,600 SqFt.
  • HILTONHEAD-509916 MLS
Courtesy of Engel & Volkers

Listing courtesy of Engel & Volkers.

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14 Kings Tree Road, Hilton Head Island image
14 Kings Tree Road, Hilton Head Island $3,195,000

Custom home with completion in August. Beautiful view across the lagoon to the 1st fairway of the Long Cove Golf Club.

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  • 5 Beds
  • 5 Baths
  • 4,447 SqFt.
  • HILTONHEAD-510707 MLS
Courtesy of Charter One Realty

Listing courtesy of Charter One Realty.

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5 Junket, Hilton Head Island image
5 Junket, Hilton Head Island $4,995,000

LOVE AT FIRST SIGHT! Welcome to 5 Junket, a stunning coastal estate nestled on a premier second-row homesite in one of the most coveted locations within Palmetto Dunes, w...

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  • 6 Beds
  • 7 Baths
  • 3,702 SqFt.
  • HILTONHEAD-510711 MLS
Courtesy of Harbour & Home Real Estate

Listing courtesy of Harbour & Home Real Estate.

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19 Parkwood Drive, Hilton Head Island image
19 Parkwood Drive, Hilton Head Island $1,288,000

Lovingly cared for 5 bedroom, 3.5 bath home ideally situated on a desirable cul-de- sac near the front entrance of HHP. Sunlight fills the home through abundant windows, ...

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  • 5 Beds
  • 4 Baths
  • 3,450 SqFt.
  • HILTONHEAD-510561 MLS
Courtesy of Howard Hanna Allen Tate Lowcountry

Listing courtesy of Howard Hanna Allen Tate Lowcountry.

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9 Promontory Court, Hilton Head Island image
9 Promontory Court, Hilton Head Island $3,295,000

Welcome to 9 Promontory Court. This remarkable 5-bedroom, 5-bath residence enjoys a coveted location overlooking multiple holes of the George Fazio Golf Course, complemen...

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  • 5 Beds
  • 5 Baths
  • 5,019 SqFt.
  • HILTONHEAD-510120 MLS
Courtesy of Howard Hanna Allen Tate Lowcountry

Listing courtesy of Howard Hanna Allen Tate Lowcountry.

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5 Heritage Court, Hilton Head Island image
5 Heritage Court, Hilton Head Island $2,625,000

Welcome to 5 Heritage Court! This beautifully designed newer-style home offers an exceptional blend of space, comfort, and privacy in the highly sought-after Heritage Woo...

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  • 5 Beds
  • 5 Baths
  • 3,872 SqFt.
  • HILTONHEAD-510379 MLS
Courtesy of Lighthouse Realty

Listing courtesy of Lighthouse Realty.

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27 Cotesworth Place, Hilton Head Island image
27 Cotesworth Place, Hilton Head Island $2,100,000

A great Indigo Run opportunity located on one of the best streets on the 16th green of the private course. This large 5 BR, 5.5 BA, fully updated home has the popular mai...

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  • 5 Beds
  • 6 Baths
  • 4,494 SqFt.
  • HILTONHEAD-510221 MLS
Courtesy of Dunes Real Estate

Listing courtesy of Dunes 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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Hilton Head Island Homes For Sale By Villas

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Hilton Head Island Homes For Sale By New Development

  • Sunderland Point
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Search By Communities

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HiltonHeadRealtySales.com / Group DiNenna:

Dino DiNenna
Broker, Realtor, GRI, CRS
Certified Negotiation Expert (CNE®)
Southern Lifestyle Properties
PO Box 7725
Hilton Head Island, SC 29938-7725
843.560.9310 Direct
843.781.6700 Team

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Dino DiNenna, Hilton Head Real Estate Broker

 

Southern Lifestyle Properties of SC, LLC
Licensed South Carolina Real Estate Agency
Andria Garbis, Broker-in-Charge
5846 Guilford Place
Bluffton, SC 29910
843.341.9000 Main Office
843.781.6700 Team

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