The highest-value homes in Hilton Head Island

Every city has its showpiece homes — the ones that define luxury living. And as prices continue to rise across the U.S., the most valuable properties showcase just how high local markets can go. The high-end housing market in particular has reached new heights in 2025, with the typical luxury home selling for a record $1.35 million in March. The million-dollar price tag no longer even qualifies as "luxury" in most places.

So, what do Hilton Head Island's most glamorous homes look like? To find out, Redfin Real Estate found the city's highest-value homes based on their Redfin Estimate.

#1. 80 Bridgetown Ln, Hilton Head Island, SC 29928
- Approximate home value: $16,356,904
- Beds: 8
- Baths: 13
- Square feet: 18,056
- See 80 Bridgetown Ln, Hilton Head Island, SC 29928 on Redfin.com

#2. 38 Surf Scoter Rd, Hilton Head Island, SC 29928
- Approximate home value: $15,498,544
- Beds: 6
- Baths: 8
- Square feet: 10,628
- See 38 Surf Scoter Rd, Hilton Head Island, SC 29928 on Redfin.com

#3. 7 S Beach Lagoon Rd, Hilton Head Island, SC 29928
- Approximate home value: $14,292,266
- Beds: 6
- Baths: 6.5
- Square feet: 8,123
- See 7 S Beach Lagoon Rd, Hilton Head Island, SC 29928 on Redfin.com

#4. 14 Painted Bunting Rd, Hilton Head Island, SC 29928
- Approximate home value: $14,270,918
- Beds: 5
- Baths: not available
- Square feet: 7,314
- See 14 Painted Bunting Rd, Hilton Head Island, SC 29928 on Redfin.com

#5. 9 Brown Pelican Rd, Hilton Head Island, SC 29928
- Approximate home value: $13,927,913
- Beds: 6
- Baths: 8
- Square feet: 7,000
- See 9 Brown Pelican Rd, Hilton Head Island, SC 29928 on Redfin.com

#6. 24 Oyster Catcher Rd, Hilton Head Island, SC 29928
- Approximate home value: $13,185,169
- Beds: 4
- Baths: 12
- Square feet: 5,995
- See 24 Oyster Catcher Rd, Hilton Head Island, SC 29928 on Redfin.com

#7. 14 Laughing Gull Rd, Hilton Head Island, SC 29928
- Approximate home value: $13,168,925
- Beds: 1
- Baths: not available
- Square feet: 10,698
- See 14 Laughing Gull Rd, Hilton Head Island, SC 29928 on Redfin.com

#8. 15 Bald Eagle Rd, Hilton Head Island, SC 29928
- Approximate home value: $12,352,856
- Beds: 1
- Baths: not available
- Square feet: 3,958
- See 15 Bald Eagle Rd, Hilton Head Island, SC 29928 on Redfin.com

#9. 14 Whistling Swan Rd, Hilton Head Island, SC 29928
- Approximate home value: $12,237,551
- Beds: 4
- Baths: 8
- Square feet: 5,855
- See 14 Whistling Swan Rd, Hilton Head Island, SC 29928 on Redfin.com

#10. 14 Seaside Sparrow Rd, Hilton Head Island, SC 29928
- Approximate home value: $12,175,435
- Beds: 6
- Baths: not available
- Square feet: 5,407
- See 14 Seaside Sparrow Rd, Hilton Head Island, SC 29928 on Redfin.com

#11. 37 S Beach Lagoon Rd, Hilton Head Island, SC 29928
- Approximate home value: $12,160,993
- Beds: 4
- Baths: not available
- Square feet: 6,253
- See 37 S Beach Lagoon Rd, Hilton Head Island, SC 29928 on Redfin.com

#12. 19 Red Cardinal Rd, Hilton Head Island, SC 29928
- Approximate home value: $11,649,760
- Beds: 5
- Baths: not available
- Square feet: 6,007
- See 19 Red Cardinal Rd, Hilton Head Island, SC 29928 on Redfin.com

#13. 19 S Beach Lagoon Rd, Hilton Head Island, SC 29928
- Approximate home value: $11,362,607
- Beds: 6
- Baths: 8
- Square feet: 5,948
- See 19 S Beach Lagoon Rd, Hilton Head Island, SC 29928 on Redfin.com

#14. 15 Laughing Gull Rd, Hilton Head Island, SC 29928
- Approximate home value: $11,184,670
- Beds: 7
- Baths: 9
- Square feet: 9,320
- See 15 Laughing Gull Rd, Hilton Head Island, SC 29928 on Redfin.com

#15. 25 Sandhill Crane Rd, Hilton Head Island, SC 29928
- Approximate home value: $11,128,391
- Beds: 6
- Baths: not available
- Square feet: 6,309
- See 25 Sandhill Crane Rd, Hilton Head Island, SC 29928 on Redfin.com

#16. 31 S Beach Lagoon Rd, Hilton Head Island, SC 29928
- Approximate home value: $10,970,046
- Beds: 4
- Baths: 8
- Square feet: 6,752
- See 31 S Beach Lagoon Rd, Hilton Head Island, SC 29928 on Redfin.com

#17. 43 S Beach Lagoon Rd, Hilton Head Island, SC 29928
- Approximate home value: $10,950,501
- Beds: 2
- Baths: not available
- Square feet: 8,017
- See 43 S Beach Lagoon Rd, Hilton Head Island, SC 29928 on Redfin.com

Methodology

Redfin Estimate data as of September 11, 2025. Bedroom, bathroom, and square footage data may not be available or accurate. Secondary addresses may not be included. Value estimates may not reflect what the house could actually sell for.