Most expensive homes for sale in Hilton Head Island
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April 29, 2025
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Most expensive homes for sale in Hilton Head Island
Stacker compiled a list of the most expensive homes in Hilton Head Island listed for sale on realtor.com. Homes are ranked by price with ties broken by price per square foot.
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#30. 85 Plantation Dr, Hilton Head Island
- Price: $4,849,000
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 5,844
- Price per square foot: $829
- Days on market: 20 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 5,844
- Price per square foot: $829
- Days on market: 20 days
- View listing on realtor.com
#29. 58 N Sea Pines Dr, Hilton Head Island
- Price: $4,900,000
- 5 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 6,631
- Price per square foot: $738
- Days on market: 82 days
- View listing on realtor.com
- 5 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 6,631
- Price per square foot: $738
- Days on market: 82 days
- View listing on realtor.com
#28. 29 Baynard Park Rd, Hilton Head Island
- Price: $4,995,000
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 3,742
- Price per square foot: $1,334
- Days on market: 37 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 3,742
- Price per square foot: $1,334
- Days on market: 37 days
- View listing on realtor.com
#27. 9 Armada St, Hilton Head Island
- Price: $5,250,000
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 6,741
- Price per square foot: $778
- Days on market: 53 days
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 6,741
- Price per square foot: $778
- Days on market: 53 days
- View listing on realtor.com
#26. 25 N Calibogue Cay Rd, Hilton Head Island
- Price: $5,500,000
- 6 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 4,146
- Price per square foot: $1,326
- Days on market: 64 days (-$300,000 price reduction since listing)
- View listing on realtor.com
- 6 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 4,146
- Price per square foot: $1,326
- Days on market: 64 days (-$300,000 price reduction since listing)
- View listing on realtor.com
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#25. 12 Cassina Ln, Hilton Head Island
- Price: $5,595,000
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 3,913
- Price per square foot: $1,429
- Days on market: 101 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 3,913
- Price per square foot: $1,429
- Days on market: 101 days
- View listing on realtor.com
#24. 34 W Beach Lagoon Rd, Hilton Head Island
- Price: $5,700,000
- 4 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 2,872
- Price per square foot: $1,984
- Days on market: 51 days (-$250,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 2,872
- Price per square foot: $1,984
- Days on market: 51 days (-$250,000 price reduction since listing)
- View listing on realtor.com
#23. 8 Sea Front Ln, Hilton Head Island
- Price: $5,750,000
- 10 bedrooms, 10 full bathrooms, 2 half bathrooms
- Square feet: 6,771
- Price per square foot: $849
- Days on market: 34 days
- View listing on realtor.com
- 10 bedrooms, 10 full bathrooms, 2 half bathrooms
- Square feet: 6,771
- Price per square foot: $849
- Days on market: 34 days
- View listing on realtor.com
#22. 10 Brams Point Rd, Hilton Head Island
- Price: $5,850,000
- 4 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 5,941
- Price per square foot: $984
- Days on market: 233 days (-$145,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 5,941
- Price per square foot: $984
- Days on market: 233 days (-$145,000 price reduction since listing)
- View listing on realtor.com
#21. 11 N Calibogue Cay Rd, Hilton Head Island
- Price: $5,950,000
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 6,473
- Price per square foot: $919
- Days on market: 450 days (-$300,000 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 6,473
- Price per square foot: $919
- Days on market: 450 days (-$300,000 price reduction since listing)
- View listing on realtor.com
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#20. 34 W Beach Lagoon Dr, Hilton Head Island
- Price: $5,950,000
- 4 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 2,872
- Price per square foot: $2,071
- Lot size: 1.6 acres
- Days on market: 52 days
- View listing on realtor.com
- 4 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 2,872
- Price per square foot: $2,071
- Lot size: 1.6 acres
- Days on market: 52 days
- View listing on realtor.com
#19. 30 W Beach Lagoon Dr, Hilton Head Island
- Price: $6,195,000
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 4,226
- Price per square foot: $1,465
- Lot size: 0.7 acres
- Days on market: 86 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 4,226
- Price per square foot: $1,465
- Lot size: 0.7 acres
- Days on market: 86 days
- View listing on realtor.com
#18. 19 W Beach Lagoon Rd, Hilton Head Island
- Price: $6,295,000
- 7 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 6,523
- Price per square foot: $965
- Days on market: 73 days
- View listing on realtor.com
- 7 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 6,523
- Price per square foot: $965
- Days on market: 73 days
- View listing on realtor.com
#17. 28 Planters Row, Hilton Head Island
- Price: $6,895,000
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 6,346
- Price per square foot: $1,086
- Days on market: 65 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 6,346
- Price per square foot: $1,086
- Days on market: 65 days
- View listing on realtor.com
#16. 206 N Sea Pines Dr, Hilton Head Island
- Price: $6,900,000
- 7 bedrooms, 7 full bathrooms, 1 half bathroom
- Square feet: 8,560
- Price per square foot: $806
- Days on market: 227 days (-$595,000 price reduction since listing)
- View listing on realtor.com
- 7 bedrooms, 7 full bathrooms, 1 half bathroom
- Square feet: 8,560
- Price per square foot: $806
- Days on market: 227 days (-$595,000 price reduction since listing)
- View listing on realtor.com
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#15. 70 Brams Point Rd, Hilton Head Island
- Price: $7,000,000
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 8,000
- Price per square foot: $875
- Days on market: 562 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 8,000
- Price per square foot: $875
- Days on market: 562 days
- View listing on realtor.com
#14. 73 Brams Point Rd, Hilton Head Island
- Price: $7,200,000
- 4 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 7,183
- Price per square foot: $1,002
- Days on market: 53 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 7,183
- Price per square foot: $1,002
- Days on market: 53 days
- View listing on realtor.com
#13. 18 Armada St, Hilton Head Island
- Price: $7,375,000
- 6 bedrooms, 7 full bathrooms
- Square feet: 6,398
- Price per square foot: $1,152
- Days on market: 256 days (-$120,000 price reduction since listing)
- View listing on realtor.com
- 6 bedrooms, 7 full bathrooms
- Square feet: 6,398
- Price per square foot: $1,152
- Days on market: 256 days (-$120,000 price reduction since listing)
- View listing on realtor.com
#12. 16 Oyster Shell Ln, Hilton Head Island
- Price: $7,449,000
- 5 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 9,287
- Price per square foot: $802
- Days on market: 3 days
- View listing on realtor.com
- 5 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 9,287
- Price per square foot: $802
- Days on market: 3 days
- View listing on realtor.com
#11. 67 Baynard Park Rd, Hilton Head Island
- Price: $7,495,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,743
- Price per square foot: $1,580
- Days on market: 62 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,743
- Price per square foot: $1,580
- Days on market: 62 days
- View listing on realtor.com
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#10. 9 Bayberry Ln, Hilton Head Island
- Price: $7,599,000
- 5 bedrooms, 5 full bathrooms
- Square feet: 3,641
- Price per square foot: $2,087
- Days on market: 53 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms
- Square feet: 3,641
- Price per square foot: $2,087
- Days on market: 53 days
- View listing on realtor.com
#9. 15 Dune Ln, Hilton Head Island
- Price: $7,900,000
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 4,677
- Price per square foot: $1,689
- Days on market: 46 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 4,677
- Price per square foot: $1,689
- Days on market: 46 days
- View listing on realtor.com
#8. 34 Brams Point Rd, Hilton Head Island
- Price: $7,995,000
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 6,295
- Price per square foot: $1,270
- Days on market: 23 days
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 6,295
- Price per square foot: $1,270
- Days on market: 23 days
- View listing on realtor.com
#7. 6 Overlook Pl, Hilton Head Island
- Price: $8,200,000
- 6 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 8,661
- Price per square foot: $946
- Days on market: 144 days
- View listing on realtor.com
- 6 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 8,661
- Price per square foot: $946
- Days on market: 144 days
- View listing on realtor.com
#6. 36 Ruddy Turnstone Rd, Hilton Head Island
- Price: $8,999,999
- 5 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 5,386
- Price per square foot: $1,670
- Days on market: 15 days
- View listing on realtor.com
- 5 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 5,386
- Price per square foot: $1,670
- Days on market: 15 days
- View listing on realtor.com
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#5. 90 Tidewater Mnr, Hilton Head Island
- Price: $10,750,000
- 5 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 8,025
- Price per square foot: $1,339
- Days on market: 30 days
- View listing on realtor.com
- 5 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 8,025
- Price per square foot: $1,339
- Days on market: 30 days
- View listing on realtor.com
#4. 15 Bald Eagle Rd, Hilton Head Island
- Price: $13,875,000
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 6,500
- Price per square foot: $2,134
- Days on market: 586 days (-$100,000 price reduction since listing)
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 6,500
- Price per square foot: $2,134
- Days on market: 586 days (-$100,000 price reduction since listing)
- View listing on realtor.com
#3. 9 Brown Pelican Rd, Hilton Head Island
- Price: $15,000,000
- 6 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 7,000
- Price per square foot: $2,142
- Days on market: 64 days
- View listing on realtor.com
- 6 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 7,000
- Price per square foot: $2,142
- Days on market: 64 days
- View listing on realtor.com
#2. 7 S Beach Lagoon Rd, Hilton Head Island
- Price: $15,200,000
- 6 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 6,562
- Price per square foot: $2,316
- Days on market: 12 days
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 6,562
- Price per square foot: $2,316
- Days on market: 12 days
- View listing on realtor.com
#1. 80 Bridgetown Ln, Hilton Head Island
- Price: $18,000,000
- 8 bedrooms, 11 full bathrooms, 4 half bathrooms
- Square feet: 18,083
- Price per square foot: $995
- Days on market: 3 days
- View listing on realtor.com
- 8 bedrooms, 11 full bathrooms, 4 half bathrooms
- Square feet: 18,083
- Price per square foot: $995
- Days on market: 3 days
- View listing on realtor.com
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