5 Sold Hilton Head Island Waterfront and Resort-Style Retreats

Along the water’s edge in Spanish Wells on Hilton Head Island, this 2016 custom-built Mediterranean residence is designed for deepwater living, with spectacular views and a fully equipped dock offering large-vessel capability and a boat lift. Inside, attention to detail shows in custom beams and woodwork throughout, anchoring spaces that balance comfort and purpose: a chef’s kitchen, an office, a gym, and a media room for quieter evenings in. The layout includes four bedrooms with an optional fifth, plus six baths, with spacious en suite bedrooms that keep everyday routines feeling unhurried. Set privately on over an acre, the outdoor setting reads like a second home of its own, with a lavish second living area, an entertainer’s pool and spa, and a poolside kitchen and grill—made for long afternoons that drift easily into night.

Price: $5,495,000 (Sold)

Along the water’s edge on Broad Creek, this renovated Hilton Head Island residence pairs deep-water access with a resort-minded outdoor setting. A private dock with boat lift makes time on the water feel effortless, while a stone-lined flowing pool—with slide and waterfall—anchors days spent outside. The layout extends naturally to an outdoor kitchen and a swim-up bar, with ample space for gathering amid a carefully composed landscape. Inside, an open floor plan keeps the mood airy and connected, and the entire home is oriented to capture picturesque water views. Spacious living areas support both quiet mornings and lively evenings. Practical touches include an oversized 3+ garage with generous storage, plus a Tesla Powerwall and solar roof array for on-site power generation and backup protection—an easy fit for modern coastal life.

Price: $4,500,000 (Sold)

On a quiet stretch of Sea Pines, 58 Heritage Road captures the easy rhythm of Hilton Head Island living, with views across the 12th hole of Harbour Town Golf Links. Offered as a short-term rental through The Vacation Company, the residence is spacious and elegantly designed for gatherings, featuring 4 bedrooms and 4 bathrooms alongside a gourmet kitchen that anchors time together. A screened-in porch extends the living space outdoors, inviting slow mornings and unhurried evenings after a day on the island. The setting feels calm and welcoming, well suited to family reunions, friends’ getaways, or a simple reset. Looking ahead, the property is slated for a Spring 2026 upgrade to a 6-bedroom vacation home, adding even more flexibility for larger groups and shared moments.

Price: $2,950,000 (Sold)

Steps from the shoreline on Hilton Head Island, 52 Wicklow Drive is a custom Wexford residence set on an elegant cul-de-sac, with standout curb appeal and a welcoming arrival. Inside, recent updates keep the interiors feeling crisp and cared for, including fresh paint, sanded-and-sealed wood floors, and epoxied garage floors. The spacious plan balances formality and everyday ease, with formal living and dining rooms flowing to an open kitchen, plus an upstairs sitting area and a dedicated bonus/craft room. Four bedrooms are joined by four full and two half baths, along with a home office that can flex as an optional fifth bedroom. For those who value storage and hobbies as much as square footage, the expansive 3,400-square-foot drive-through garage—with space for up to five cars and a golf cart bay—sets the tone for unhurried, well-organized living.

Price: $2,100,000 (Sold)

Steps from the shoreline in Palmetto Dunes, this beautifully renovated 2BR/2BA townhouse in Ocean Cove pairs a relaxed coastal setting with clean, modern finishes. Granite countertops, sleek tile flooring, and stainless steel appliances anchor a kitchen designed for easy family gatherings and effortless everyday cooking. An extension off the back expands the living area into a generous great room—an inviting place to entertain, unwind, or simply settle into the rhythm of island life. Outside your door, natural beauty and the sand and sea are close at hand, with the beach and Dunes House just a short stroll away. Palmetto Dunes rounds out the experience with tennis and pickleball, bike trails, pools, and dining options, making it easy to spend more time outdoors and less time planning.

Price: $809,000 (Sold)