Hilton Head Plantation

Hilton Head Plantation spans approximately 4,000 acres at the north end of Hilton Head Island, nestled between Port Royal Sound and the Intracoastal Waterway/Skull Creek. It is one of the island's largest and most established master-planned communities, home to roughly 10,000 residents across more than 4,000 single-family homes and around 500 villas and townhomes spread throughout distinct neighborhoods like Oyster Reef, The Headlands, Crooked Pond, Hickory Forest, Seabrook Landing, The Rookery, and Big Woods — each with its own character ranging from wooded interior lots to golf-course frontage to deep-water Port Royal Sound estates. The golf scene is central to the lifestyle. Four 18-hole championship courses sit inside the gates: the Country Club of Hilton Head (private, full-service ClubCorp club designed by Rees Jones with tennis, fitness center, indoor and outdoor pools, and a restaurant), Bear Creek (private, Rees Jones, capped at ~250 members), Oyster Reef (semi-private, Rees Jones, award-winning), and Dolphin Head (semi-private, designed by Gary Player and Ron Kirby). Club memberships are entirely optional — unusual on Hilton Head — so residents can golf as much or as little as they want without a mandatory buy-in. Beyond golf, the plantation is built around several POA-run amenity hubs. The Dolphin Head Recreation Area on Port Royal Sound is the crown jewel: a recently renovated complex with a boardwalk to Pine Island's private beach access (with roughly 2 miles of walking beach), a custom playground, an event lawn, and a multi-use court that converts from basketball to three pickleball courts. The adjacent 0.9-mile Bluff Walk offers deep-water sound views. The Spring Lake Recreation Area anchors the community's interior with a pool complex, tennis courts, the Spring Lake Racquet Club, and a clubhouse. The Plantation House hosts social events, club meetings, and year-round programming. Skull Creek Marina — a full-service commercial marina inside the gates — provides slips, fuel, storage, and direct Intracoastal Waterway access, with the Old Fort Pub restaurant on site. Social life is unusually rich for a community this size. The POA recognizes somewhere between 30 and 50+ resident clubs and organizations depending on how you count, including the HHP Yacht Club, Farmers Club (with its own 300-member Seabrook Farm garden plots), Newcomers & Neighbors Club, Women's Club, Corvette Club, Plantation Paddlers Kayak Club, Artists Club, Avid Gardeners, Woodcarvers, and an active pickleball club with 200+ members. The community also includes two nature conservancies — the 50-acre Cypress Conservancy and the 127-acre Whooping Crane Conservancy — with boardwalks and nature trails through preserved wetlands and forests. The plantation has three staffed gates (Main Gate, Cypress Gate, and the Squire Pope back gate) with 24-hour security, 72 miles of internal roadway, and more than 10 miles of leisure paths connecting neighborhoods to amenities. Although the gates are staffed and residential areas are private, golf courses, the marina, and restaurants are open to the public. Hilton Head Plantation is not age-restricted — it's intentionally age-diverse and home to year-round families, professionals, and retirees alike — but its emphasis on walkable amenities, clubs, golf, and waterfront living makes it a longtime favorite of retirees and second-home owners. Homes range from interior single-family properties around $600K to golf-course homes in the $800K–$1.5M range and waterfront estates on Skull Creek and Port Royal Sound reaching $3M–$7M+.