South Carolina · as of September 2026

The best luxury home agents in Hilton Head Island

12 agents who close Hilton Head Island's high end, ranked by what they sell for, how much of it is on record, and what their clients say afterward.

No. 1
J

James Wedgeworth

Charter One Realty

5.0 · 612 reviews

Avg sale
$1.2M
Top sale
$7.1M
Closed
2,655
No. 2
H

Herman and Davis Properties

Charter One Realty

5.0 · 79 reviews

Avg sale
$1.5M
Top sale
$6.5M
Closed
431
No. 3
R

Robbie Bunting

Hilton Head Properties Realty

5.0 · 143 reviews

Avg sale
$1.1M
Top sale
$6.0M
Closed
593
No. 4
J

Jeff Hunt

Jeff Hunt & Associates

5.0 · 210 reviews

Avg sale
$1.1M
Top sale
$7.9M
Closed
315
No. 5
T

The Prud'homme Team

William Raveis

5.0 · 315 reviews

Avg sale
$858K
Top sale
$8.4M
Closed
1,346
No. 6
B

Beth Drake

Keller Williams Realty

4.9 · 202 reviews

Avg sale
$892K
Top sale
$4.3M
Closed
723
No. 7
C

Collins Group Realty

Collins Group Realty

5.0 · 268 reviews

Avg sale
$763K
Top sale
$6.5M
Closed
2,177
No. 8
D

Dunes Real Estate

Dunes Real Estate

5.0 · 454 reviews

Avg sale
$800K
Top sale
$7.9M
Closed
1,143
No. 9
D

Drew Butler

Charter One Realty

5.0 · 70 reviews

Avg sale
$1.1M
Top sale
$4.6M
Closed
295
No. 10
K

Ken and Clay Oliver

Dunes Real Estate

5.0 · 142 reviews

Avg sale
$1.1M
Top sale
$5.3M
Closed
232
No. 11
R

Richard MacDonald

Charter One Realty North

5.0 · 95 reviews

Avg sale
$909K
Top sale
$2.9M
Closed
283
No. 12
L

Lea Smith

RE/MAX Island Realty

5.0 · 154 reviews

Avg sale
$880K
Top sale
$3.2M
Closed
227
Hilton Head Island represents South Carolina's premium resort and retirement real estate market, with gated plantation communities like Sea Pines, Palmetto Dunes, and Hilton Head Plantation offering world-class golf, beach access, and a resort lifestyle. The market is driven by full-time retirees, second-home buyers, and short-term rental investors. Median prices are among the highest in the state, reflecting limited land supply and lifestyle premium. Buyers should be prepared for additional costs including POA fees, flood insurance, and short-term rental regulations that vary by community. An experienced Hilton Head agent who understands plantation-specific rules is essential.

Frequently Asked Questions — Hilton Head Island Real Estate