The most expensive neighborhoods in Hilton Head Island
The most expensive neighborhoods in Hilton Head Island
Homebuyers and sellers are navigating a slow and expensive housing market, with rising prices and stagnant demand keeping many on the sidelines. This comes amid rising economic uncertainty and growing wealth concentration. But luxury homes—multimillion-dollar estates, sleek penthouses, and one-of-a-kind custom builds—are still selling, even as most buyers pull back.
Most people can't afford high-end homes, although they're still fun to dream about. So, to highlight where luxury real estate is commanding the highest prices, Redfin analyzed the most expensive neighborhoods in the Hilton Head Island metro area—and showcased a few of the area's standout listings (when possible).
Note: Redfin's analysis focused on metro areas, meaning some neighborhoods fell within smaller nearby cities. Listings and data were gathered on October 15, 2025.
#1. Oceanside (Hilton Head Island, SC)
Median sale price: $3,042,500 | Median days on market: 109 days124 N Sea Pines Dr, Hilton Head Island, SC 29928
- List price: $1,750
- Beds: 2 | Baths: 2 | Square feet: not available
- See 124 N Sea Pines Dr, Hilton Head Island, SC 29928 on Redfin.com
30 Ruddy Turnstone Rd, Hilton Head Island, SC 29928
- List price: $3,999,000
- Beds: 5 | Baths: 6 | Square feet: 3,880
- See 30 Ruddy Turnstone Rd, Hilton Head Island, SC 29928 on Redfin.com
30 E Beach Lagoon Rd, Hilton Head Island, SC 29928
- List price: $6,100,000
- Beds: 5 | Baths: 5 | Square feet: 4,449
- See 30 E Beach Lagoon Rd, Hilton Head Island, SC 29928 on Redfin.com
34 W Beach Lagoon Rd, Hilton Head Island, SC 29928
- List price: $4,950,000
- Beds: 4 | Baths: 5.5 | Square feet: 2,872
- See 34 W Beach Lagoon Rd, Hilton Head Island, SC 29928 on Redfin.com
#2. Wexford Plantation (Hilton Head Island, SC)
Median sale price: $2,050,000 | Median days on market: 84 days15 Harrogate Dr, Hilton Head Island, SC 29928
- List price: $3,295,000
- Beds: 4 | Baths: 3.5 | Square feet: 6,828
- See 15 Harrogate Dr, Hilton Head Island, SC 29928 on Redfin.com
27 Wexford Dr, Hilton Head Island, SC 29928
- List price: $3,495,000
- Beds: 5 | Baths: 5.5 | Square feet: 4,200
- See 27 Wexford Dr, Hilton Head Island, SC 29928 on Redfin.com
8 Fairfax Ln, Hilton Head Island, SC 29928
- List price: $2,449,000
- Beds: 5 | Baths: 5.5 | Square feet: 3,618
- See 8 Fairfax Ln, Hilton Head Island, SC 29928 on Redfin.com
80 Bridgetown Ln, Hilton Head Island, SC 29928
- List price: $18,000,000
- Beds: 8 | Baths: 13 | Square feet: 18,056
- See 80 Bridgetown Ln, Hilton Head Island, SC 29928 on Redfin.com
#3. South Beach (Hilton Head Island, SC)
Median sale price: $1,950,000 | Median days on market: 82 days15 Grey Widgeon Rd, Hilton Head Island, SC 29928
- List price: $10,995,000
- Beds: 7 | Baths: 8.5 | Square feet: 6,200
- See 15 Grey Widgeon Rd, Hilton Head Island, SC 29928 on Redfin.com
226 S Sea Pines Dr, Hilton Head Island, SC 29928
- List price: $950,000
- Beds: 2 | Baths: 2 | Square feet: 1,086
- See 226 S Sea Pines Dr, Hilton Head Island, SC 29928 on Redfin.com
4 Gadwall Rd, Hilton Head Island, SC 29928
- List price: $3,490,000
- Beds: 4 | Baths: 4.5 | Square feet: 3,100
- See 4 Gadwall Rd, Hilton Head Island, SC 29928 on Redfin.com
9 Royal Tern Rd, Hilton Head Island, SC 29928
- List price: $5,100,000
- Beds: 6 | Baths: 6 | Square feet: 4,344
- See 9 Royal Tern Rd, Hilton Head Island, SC 29928 on Redfin.com
#4. Berkeley Hall (Bluffton, SC)
Median sale price: $1,837,500 | Median days on market: 94 days44 Lancaster Blvd, Okatie, SC 29909
- List price: $1,963,995
- Beds: 4 | Baths: 4.5 | Square feet: 3,936
- See 44 Lancaster Blvd, Okatie, SC 29909 on Redfin.com
50 Clifton Dr, Okatie, SC 29909
- List price: $1,849,000
- Beds: 6 | Baths: 7.5 | Square feet: 5,166
- See 50 Clifton Dr, Okatie, SC 29909 on Redfin.com
6 Litchfield Ct, Okatie, SC 29909
- List price: $1,199,000
- Beds: 4 | Baths: 4 | Square feet: 3,215
- See 6 Litchfield Ct, Okatie, SC 29909 on Redfin.com
80 Clifton Dr, Okatie, SC 29909
- List price: $1,495,000
- Beds: 4 | Baths: 4.5 | Square feet: 3,761
- See 80 Clifton Dr, Okatie, SC 29909 on Redfin.com
#5. Colleton River Plantation (Port Royal, SC)
Median sale price: $1,700,000 | Median days on market: 80 days16 Hampton Ln, Bluffton, SC 29910
- List price: $8,850,000
- Beds: 5 | Baths: 7.5 | Square feet: 8,038
- See 16 Hampton Ln, Bluffton, SC 29910 on Redfin.com
3 Mackays Pt, Bluffton, SC 29910
- List price: $1,525,000
- Beds: 4 | Baths: 4.5 | Square feet: 4,323
- See 3 Mackays Pt, Bluffton, SC 29910 on Redfin.com
4 Wedgewood Cir, Bluffton, SC 29910
- List price: $1,675,000
- Beds: 4 | Baths: 4.5 | Square feet: 3,815
- See 4 Wedgewood Cir, Bluffton, SC 29910 on Redfin.com
6 Brenton Ct, Bluffton, SC 29910
- List price: $2,295,000
- Beds: 5 | Baths: 5.5 | Square feet: 4,820
- See 6 Brenton Ct, Bluffton, SC 29910 on Redfin.com
