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Holiday Homes, Hilton Head Island Real Estate

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Holiday Homes, Hilton Head Island, SC Homes for Sale

View every home for sale in Holiday Homes, Hilton Head Island 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 home in Holiday Homes, you can add it to your favorites, request more information or set up a showing.

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

Homes for sale in Holiday Homes, Hilton Head Island, SC

37 Oleander Street, Hilton Head Island image
37 Oleander Street, Hilton Head Island $2,295,000

Brand-new 7-Bedroom, 4.5 Bath Hilton Head Island home with private pool, and elevator to all floors. This spacious luxury home features 10-foot ceilings on the main level...

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  • 7 Beds
  • 5 Baths
  • 3,246 SqFt.
  • HILTONHEAD-509321 MLS
Courtesy of RE/MAX Island Realty

Listing courtesy of RE/MAX Island Realty.

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8 Azalea Street, Hilton Head Island image
8 Azalea Street, Hilton Head Island $955,000 ▼

Nestled just steps from the ocean, this charming beach cottage offers the perfect blend of coastal comfort and relaxed seaside living. Three bedrooms and two full baths p...

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  • 3 Beds
  • 2 Baths
  • 1,545 SqFt.
  • HILTONHEAD-508893 MLS
Courtesy of Charter One Realty

Listing courtesy of Charter One Realty.

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35 Oleander Street, Hilton Head Island image
35 Oleander Street, Hilton Head Island $2,295,000

Brand-new 7-Bedroom, 4.5 Bath Hilton Head Island home with private pool, and elevator to all floors. This spacious luxury home features 10-foot ceilings on the main level...

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  • 7 Beds
  • 5 Baths
  • 3,246 SqFt.
  • HILTONHEAD-506962 MLS
Courtesy of RE/MAX Island Realty

Listing courtesy of RE/MAX Island Realty.

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9 Mimosa St, Hilton Head Island image
9 Mimosa St, Hilton Head Island $1,799,999 ▼

Stunning Custom-Built 4-Bedroom Home in Prime Folly Field, Hilton Head - Steps from the Beach. Discover your dream coastal retreat in the highly desirable Folly Field nei...

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  • 4 Beds
  • 3 Baths
  • 2,523 SqFt.
  • HILTONHEAD-452326 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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Hilton Head Island Homes For Sale By Feature

  • Beachfront Condos
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  • View All Hilton Head Island Feature > > >

Hilton Head Island Homes For Sale By Neighborhood

  • Admirals Row
  • Breakers Villas
  • Broad Creek Landing
  • Calibogue Club
  • Deepwater
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  • Indigo Run
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  • View All Hilton Head Island Neighborhoods > > >

Hilton Head Island Homes For Sale By Price

  • Under $100,000
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  • Over $1,000,000

Hilton Head Island Homes For Sale By Villas

  • Beachwalk
  • Captains Walk
  • Fazio
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  • Ocean Club
  • Ocean One
  • Ocean Walk
  • Sea Cloisters
  • Sea Crest
  • Shorewood
  • Windsor

Hilton Head Island Homes For Sale By New Development

  • Sunderland Point
  • Sandcastles by the Sea
  • Latitude Margaritaville Hilton Head
  • Hilton Head Lakes

Search By Communities

  • Bluffton
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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

Content by HiltonHeadRealtySales.com

&

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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