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If you’re looking for a poster child for the notion that America is the land of opportunity, and Hilton Head Island offers more fertile soil than most for the growth of the American Dream, you could do far worse than Tristan O’Grady.

Born in the U.K. and raised in the extremely British-sounding Buckinghamshire, O’Grady spent his formative years traveling from place to place. His father, a resort developer, kept his family constantly on the move, and before he was rown the younger O’Grady had called England, Australia and South Africa home.
His wandering days ended when his father’s business in the U.S. led him to a golf vacation here on the island.

And while the life of an island nightspot operator proved too at odds with the life of a loving father of four, O’Grady launched a successful real estate career while still running Bamboo with his brother. A realtor has to be able to really sell the island, and O’Grady has a killer elevator pitch.

“When I sell real estate, I say after living on other continents, Hilton Head Island offers a better lifestyle and place to live than anywhere else in the world,” he said. “You can find bluer water or a better bar scene or a sandier beach, but when you put it all together, Hilton Head comes out on top.”

And apparently it’s not a bad place to chase down the American Dream, either.

Featured Properties

Properties

Results 1 - 9 of 9
54 Brams Point
Updated
54 Brams Point
Hilton Head Island, South Carolina, United States
Beds: 4   Baths: 5   Ft2: 6,671   Lot Size: 1   Lot Acres: 1.25   County: Beaufort   Region: Spanish Wells   

$4,699,000 $4,574,000

Multiple Listing Service of Hilton Head Island, Inc
2106 The Sea Crest Villas
2106 The Sea Crest Villas
Hilton Head Island, South Carolina, United States
Beds: 2   Baths: 2   County: Beaufort   Region: Forest Beach   

$586,500

Multiple Listing Service of Hilton Head Island, Inc
4 Hickory Lane
Updated
4 Hickory Lane
Hilton Head Island, South Carolina, United States
Beds: 3   Baths: 2   County: Beaufort   Region: Forest Beach   

$514,000

Multiple Listing Service of Hilton Head Island, Inc
32 Percheron Lane
32 Percheron Lane
Hilton Head Island, South Carolina, United States
County: Beaufort   Region: Hh/off Plantation   

$249,000

Multiple Listing Service of Hilton Head Island, Inc
3238 Seascape Villas
Updated
Pending
3238 Seascape Villas
Hilton Head Island, South Carolina, United States
Beds: 3   Baths: 3   County: Beaufort   Region: Forest Beach   

$199,000

Multiple Listing Service of Hilton Head Island, Inc
41 Shear Water Drive
41 Shear Water Drive
Hilton Head Island, South Carolina, United States
County: Beaufort   Region: Hh/off Plantation   

$199,000

Multiple Listing Service of Hilton Head Island, Inc
12 Clyde Lane
Pending
12 Clyde Lane
Hilton Head Island, South Carolina, United States
County: Beaufort   Region: Palmetto Hall   

$129,000

Multiple Listing Service of Hilton Head Island, Inc
21 Drummond Lane
21 Drummond Lane
Hilton Head Island, South Carolina, United States
County: Beaufort   Region: Indigo Run   

$79,000

Multiple Listing Service of Hilton Head Island, Inc
85 Bermuda Pointe Circle
Pending
85 Bermuda Pointe Circle
Hilton Head Island, South Carolina, United States
County: Beaufort   Region: Hh/off Plantation   

$59,000

Multiple Listing Service of Hilton Head Island, Inc

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