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Homebuyers and sellers are navigating a slow and expensive housing market, with rising prices and stagnant demand on the sidelines. This comes amid rising and growing . But luxury homes—multimillion-dollar estates, sleek penthouses, and one-of-a-kind custom builds—are , 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 days

124 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

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

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

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

#2. Wexford Plantation (Hilton Head Island, SC)

Median sale price: $2,050,000 | Median days on market: 84 days

15 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

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

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

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

#3. South Beach (Hilton Head Island, SC)

Median sale price: $1,950,000 | Median days on market: 82 days

15 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

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

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

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

#4. Berkeley Hall (Bluffton, SC)

Median sale price: $1,837,500 | Median days on market: 94 days

44 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

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

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

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

#5. Colleton River Plantation (Port Royal, SC)

Median sale price: $1,700,000 | Median days on market: 80 days

16 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

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

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

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