These are the highest-priced home sales reported in Hilton Head & Daufuskie Islands, South Carolina for the week ending November 1, 2026, and together the five sold for a combined $9.345 million. Every one is a single-family home on Hilton Head Island, with prices running from $1.38 million to $2.745 million. Two of the homes are inside the gates of Hilton Head Plantation, and three of the five have five bedrooms.
No. 1 — $2,745,000 · 155 Mooring Buoy, Hilton Head Island, South Carolina
The home at 155 Mooring Buoy is on the 11-mile lagoon system in Palmetto Dunes, with a lagoon dock of its own and views across the water. It sold for $2.745 million, furnished. The property last sold for $1.995 million in 2021.
Built in 2003, the two-story home has a Southern look from the street, with columns, shutters on the windows and brick accents, and broad verandas across both the front and the back. Outdoor life centers on a private, heated free-form pool, a large deck and a covered deck set up for dining and lounging. There is also an outdoor shower, and the community has beach access.
At 3,860 square feet, it is the largest of the five homes, with five bedrooms, five full baths and a half bath, and a three-car garage. It has two primary suites, one on each floor, and a three-stop elevator connects the levels. The main level has the living room, an eat-in kitchen with a bar area, a powder room, laundry and a dining room that can double as a den, office or extra sleeping space. The second primary suite shares the upper level with three more bedrooms. Inside, there are vaulted and cathedral ceilings, a sunken living room, a fireplace and floors of wood, tile and carpet.
Philip Schembra of Schembra Real Estate Group was the listing agent for the week’s top sale, and Amy Aurelio & Associates of Keller Williams Realty represented the buyer.
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No. 2 — $2,000,000 · 18 Canvasback Road, Hilton Head Island, South Carolina
The oldest of the five homes dates to 1974 and stands at 18 Canvasback Road, in the Canvasback neighborhood. It sold for $2 million.
The two-story, wood-sided home is built around an inverted floor plan, with five bedrooms, four bathrooms and 3,214 square feet. Inside are vaulted ceilings, skylights, built-in bookcases, a fireplace and a dumbwaiter, along with a bright den that can serve as more living space or a home office. The primary suite is on the upper level, floors are bamboo, tile and luxury vinyl plank, and there is a workshop and a two-car garage.
Outside, the private saltwater pool is fenced and heated. The home also has an upper deck and a screened porch, and the community offers beach access, a marina, a clubhouse and trails.
Bobby Blakley of Engel & Volkers was the listing agent, and Brandon Greenplate of Greenplate Group Brokered by eXp Realty represented the buyer.
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No. 3 — $1,670,000 · 9 Cannon Row, Hilton Head Island, South Carolina
At 9 Cannon Row in Heritage Woods, a wall of French doors in the living room fills the home with daylight and opens the view to a lagoon. Past the entry foyer, that living room rises to a tall ceiling. The open kitchen has a large center island with seating, and the dining area is ringed by windows.
The traditional two-story home, built in 1992, sold for $1.67 million. It is the most compact of the five, with 2,414 square feet on an 8,276-square-foot lot, and it has three bedrooms, three full baths and a half bath. The primary suite is on the first floor, along with a dedicated office. Upstairs, each of two guest bedrooms has its own bath. A screened porch, an outdoor shower, wood and tile floors, a workshop and a two-car garage round out the home, and owners have beach access.
Sara Kurtz of Howard Hanna Allen Tate Lowcountry was the listing agent, and Tracey Kersteen of Sea Pines Real Estate – Beach Club represented the buyer.
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No. 4 — $1,550,000 · 21 Ribaut Drive, Hilton Head Island, South Carolina
Ribaut Island is a privately gated section of Hilton Head Plantation with 63 homesites, and it keeps its own community pool, dock, and tennis and pickleball courts. The home at 21 Ribaut Drive sold there for $1.55 million, furnished. The property last sold for $660,000 in 2014.
It is the only one-story home among the five, a 1998 stucco and masonry home of 3,505 square feet on 0.42 acres, the largest lot of the group. The updated floor plan has four bedrooms, four full baths and a half bath. An open kitchen and family room are equipped for cooking with a propane stove and oven, and the primary bath has been renovated with a large soaking tub. An office sits just off the primary suite. Wood floors run through the living areas, with carpet in the bedrooms.
Outside are a courtyard, an outdoor fireplace, a deck, a patio and front and rear porches. The extended two-car garage has room for a workshop, and a walk-in attic with a floor adds storage. Beyond the island’s own gate, Hilton Head Plantation residents have a full-service marina, leisure trails, the Country Club of Hilton Head, four championship golf courses and the Dolphin Head Recreation Area.
The home went under contract 12 days after it was listed. The Reed Team of Charter One Realty was the listing agent, and Bruce Tuttle of Hilton Head Properties represented the buyer.
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No. 5 — $1,380,000 · 24 Angel Wing Drive, Hilton Head Island, South Carolina
Port Royal Sound is a three-minute walk from 24 Angel Wing Drive, and Dolphin Head Beach is a five-minute bike ride away. The home is in Dolphin Head, within Hilton Head Plantation, and it looks out on a golf course.
Built in 1979, the two-story home has five bedrooms, three bathrooms and 3,235 square feet on 0.33 acres. Its kitchen has quartz countertops, a large center island, a roomy pantry and stainless steel appliances, and it opens to a formal dining room and a living area under cathedral ceilings with a gas fireplace. A Carolina room leads out to a paver patio and a heated saltwater pool.
The primary suite is on the main level, with two large walk-in closets, its own bath and a door to a screened porch. Two more bedrooms are also on the first floor. Upstairs, a loft can serve as an office or media room, and two guest bedrooms share a full bath. Plantation residents have private beach access, a marina, tennis, pickleball and bocce courts, leisure trails and a community pool with a lazy river.
The home went under contract 17 days after it was listed and sold for $1.38 million, just above its asking price of $1.375 million. The property last sold for $1.21 million in 2023. BD Coastal Living Team of Keller Williams Realty was the listing agent, and Drew Butler of Charter One Realty represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, November 1, 2026. The report may exclude private, off-market, delayed or nondisclosed transactions. Prices, property details and professional representation are reported as available at publication and may be updated following confirmation from transaction participants.
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