Most expensive homes for sale in Hilton Head Island
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November 17, 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.
#30. 25 N Calibogue Cay Rd, Hilton Head Island
- Price: $4,750,000
- 6 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 4,146
- Price per square foot: $1,145
- Days on market: 281 days (-$150,000 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: $1,145
- Days on market: 281 days (-$150,000 price reduction since listing)
- View listing on realtor.com
#29. 29 Baynard Park Rd, Hilton Head Island
- Price: $4,800,000
- 4 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 3,742
- Price per square foot: $1,282
- Days on market: 254 days (-$195,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 3,742
- Price per square foot: $1,282
- Days on market: 254 days (-$195,000 price reduction since listing)
- View listing on realtor.com
#28. 170 Dillon Rd, Hilton Head Island
- Price: $4,900,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 2,216
- Price per square foot: $2,211
- Lot size: 0.7 acres
- Days on market: 111 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 2,216
- Price per square foot: $2,211
- Lot size: 0.7 acres
- Days on market: 111 days
- View listing on realtor.com
#27. 34 W Beach Lagoon Rd, Hilton Head Island
- Price: $4,950,000
- 4 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 2,872
- Price per square foot: $1,723
- Lot size: 1.6 acres
- Days on market: 269 days (-$445,000 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: $1,723
- Lot size: 1.6 acres
- Days on market: 269 days (-$445,000 price reduction since listing)
- View listing on realtor.com
#26. 9 Armada St, Hilton Head Island
- Price: $4,995,000
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 6,741
- Price per square foot: $740
- Days on market: 270 days (-$255,000 price reduction since listing)
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 6,741
- Price per square foot: $740
- Days on market: 270 days (-$255,000 price reduction since listing)
- View listing on realtor.com
#25. 9 Royal Tern Rd, Hilton Head Island
- Price: $5,100,000
- 6 bedrooms, 6 full bathrooms
- Square feet: 4,344
- Price per square foot: $1,174
- Days on market: 58 days
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- 6 bedrooms, 6 full bathrooms
- Square feet: 4,344
- Price per square foot: $1,174
- Days on market: 58 days
- View listing on realtor.com
#24. 134 Dune Ln, Hilton Head Island
- Price: $5,250,000
- 7 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 4,395
- Price per square foot: $1,194
- Lot size: 0.2 acres
- Days on market: 93 days (-$50,000 price reduction since listing)
- View listing on realtor.com
- 7 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 4,395
- Price per square foot: $1,194
- Lot size: 0.2 acres
- Days on market: 93 days (-$50,000 price reduction since listing)
- View listing on realtor.com
#23. 11 Marsh Dr, Hilton Head Island
- Price: $5,500,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,071
- Price per square foot: $1,084
- Days on market: 128 days (-$250,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,071
- Price per square foot: $1,084
- Days on market: 128 days (-$250,000 price reduction since listing)
- View listing on realtor.com
#22. 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: 318 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: 318 days
- View listing on realtor.com
#21. 116 Mooring Buoy, Hilton Head Island
- Price: $5,600,000
- 5 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 4,803
- Price per square foot: $1,165
- Days on market: 51 days (-$200,000 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 4,803
- Price per square foot: $1,165
- Days on market: 51 days (-$200,000 price reduction since listing)
- View listing on realtor.com
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#20. 10 Brams Point Rd, Hilton Head Island
- Price: $5,725,000
- 4 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 5,941
- Price per square foot: $963
- Days on market: 178 days (-$125,000 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: $963
- Days on market: 178 days (-$125,000 price reduction since listing)
- View listing on realtor.com
#19. 11 N Calibogue Cay Rd, Hilton Head Island
- Price: $5,750,000
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 6,473
- Price per square foot: $888
- Days on market: 667 days (-$200,000 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: $888
- Days on market: 667 days (-$200,000 price reduction since listing)
- View listing on realtor.com
#18. 30 E Beach Lagoon Rd, Hilton Head Island
- Price: $6,100,000
- 5 bedrooms, 5 full bathrooms
- Square feet: 4,449
- Price per square foot: $1,371
- Days on market: 132 days (-$400,000 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms
- Square feet: 4,449
- Price per square foot: $1,371
- Days on market: 132 days (-$400,000 price reduction since listing)
- View listing on realtor.com
#17. 73 Brams Point Rd, Hilton Head Island
- Price: $6,500,000
- 4 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 7,183
- Price per square foot: $904
- Days on market: 270 days (-$250,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 2 half bathrooms
- Square feet: 7,183
- Price per square foot: $904
- Days on market: 270 days (-$250,000 price reduction since listing)
- View listing on realtor.com
#16. 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: 75 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: 75 days
- View listing on realtor.com
#15. 18 Armada St, Hilton Head Island
- Price: $7,149,995
- 6 bedrooms, 7 full bathrooms
- Square feet: 6,398
- Price per square foot: $1,117
- Days on market: 473 days (-$149,005 price reduction since listing)
- View listing on realtor.com
- 6 bedrooms, 7 full bathrooms
- Square feet: 6,398
- Price per square foot: $1,117
- Days on market: 473 days (-$149,005 price reduction since listing)
- View listing on realtor.com
#14. 9 Bayberry Ln, Hilton Head Island
- Price: $7,300,000
- 5 bedrooms, 5 full bathrooms
- Square feet: 3,641
- Price per square foot: $2,004
- Days on market: 270 days (-$100,000 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms
- Square feet: 3,641
- Price per square foot: $2,004
- Days on market: 270 days (-$100,000 price reduction since listing)
- View listing on realtor.com
#13. 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: 220 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: 220 days
- View listing on realtor.com
#12. 11 Armada St, Hilton Head Island
- Price: $7,500,000
- 6 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 5,736
- Price per square foot: $1,307
- Days on market: 187 days
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 5,736
- Price per square foot: $1,307
- Days on market: 187 days
- View listing on realtor.com
#11. 34 Brams Point Rd, Hilton Head Island
- Price: $7,595,000
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 6,295
- Price per square foot: $1,206
- Lot size: 1.6 acres
- Days on market: 47 days
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 6,295
- Price per square foot: $1,206
- Lot size: 1.6 acres
- Days on market: 47 days
- View listing on realtor.com
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#10. 37 Dune Ln, Hilton Head Island
- Price: $7,700,000
- 7 bedrooms, 7 full bathrooms, 1 half bathroom
- Square feet: 5,918
- Price per square foot: $1,301
- Days on market: 60 days
- View listing on realtor.com
- 7 bedrooms, 7 full bathrooms, 1 half bathroom
- Square feet: 5,918
- Price per square foot: $1,301
- Days on market: 60 days
- View listing on realtor.com
#9. 10 Collier Beach Rd, Hilton Head Island
- Price: $7,950,000
- 6 bedrooms, 7 full bathrooms, 1 half bathroom
- Square feet: 3,274
- Price per square foot: $2,428
- Days on market: 4 days
- View listing on realtor.com
- 6 bedrooms, 7 full bathrooms, 1 half bathroom
- Square feet: 3,274
- Price per square foot: $2,428
- Days on market: 4 days
- View listing on realtor.com
#8. 16 Juniper Ln, Hilton Head Island
- Price: $8,400,000
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 4,097
- Price per square foot: $2,050
- Days on market: 110 days
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 4,097
- Price per square foot: $2,050
- Days on market: 110 days
- View listing on realtor.com
#7. 3 Stella Del Mare Mnr, Hilton Head Island
- Price: $8,500,000
- 4 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 5,831
- Price per square foot: $1,457
- Lot size: 0.5 acres
- Days on market: 165 days
- View listing on realtor.com
- 4 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 5,831
- Price per square foot: $1,457
- Lot size: 0.5 acres
- Days on market: 165 days
- View listing on realtor.com
#6. 5 Marsh Dr, Hilton Head Island
- Price: $8,900,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,926
- Price per square foot: $2,266
- Days on market: 86 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 3,926
- Price per square foot: $2,266
- Days on market: 86 days
- View listing on realtor.com
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#5. 28 Green Heron Rd, Hilton Head Island
- Price: $9,975,000
- 5 bedrooms, 5 full bathrooms
- Square feet: 3,962
- Price per square foot: $2,517
- Lot size: 0.5 acres
- Days on market: 144 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms
- Square feet: 3,962
- Price per square foot: $2,517
- Lot size: 0.5 acres
- Days on market: 144 days
- View listing on realtor.com
#4. 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: 247 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: 247 days
- View listing on realtor.com
#3. 15 Grey Widgeon Rd, Hilton Head Island
- Price: $10,995,000
- 7 bedrooms, 8 full bathrooms, 1 half bathroom
- Square feet: 6,200
- Price per square foot: $1,773
- Days on market: 133 days (-$500,000 price reduction since listing)
- View listing on realtor.com
- 7 bedrooms, 8 full bathrooms, 1 half bathroom
- Square feet: 6,200
- Price per square foot: $1,773
- Days on market: 133 days (-$500,000 price reduction since listing)
- View listing on realtor.com
#2. 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: 281 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: 281 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: 220 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: 220 days
- View listing on realtor.com
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