Hilton Head Island

In Sea Pines, no building breaks the tree line, street signs blend with nature and uniform mailboxes decorate the streets. "That green that you see on every mailbox is what we like to call 'Sea Pines' green," says local broker Maria Skrip, co-owner of RE/MAX Dream. Skrip lives in Bluffton but has sold homes on the Island for nearly 15 years. "When you move in, you have to go to the Sea Pines POA office, and they'll give you this little thing of paint so you can paint your mailbox. It helps keep the community pretty." Championship golf courses, a vibrant yacht basin and a New England-style shopping quarter help bring Sea Pines to life, but small touches like those classic Sea Pines mailboxes are what leave Skrip calling the community the "gem of the Island." Founding Sea Pines developer Charles Fraser wanted to create a community that mirrored Mediterranean port villages like Portofino, Italy while also preserving the land. Fraser's main goal was to set aside protected land for preserves and parks and for all development to complement the environment instead of obstructing it. "There are height and sign restrictions, and you won't see high-rise condos or a neon sign anywhere in Sea Pines or on the Island," Skrip says. "When my office was over here on the Island, the reds, whites and blues of my sign had to be toned down so it could blend in more with nature." Golf courses hug the marshes, mansions sit along the beaches and shopping districts overlook the Calibogue Sound. And while over 2 million residents visit Sea Pines annually, the resort retains a quiet feel with an uninterrupted oceanfront setting. Sea Pines features several sub-communities home to a mix of permanent residents, second homeowners and investment properties that folks rent out for vacation. Housing styles vary, but a few older homes followed a trend. "We actually have a thing where we go 'You know, it's like those Sea Pines Homes,' which are the original homes here," Skrip says, "And when they say that, I immediately picture a ranch, usually from the 1970s." Many of these homes still stand today, but buyers are purchasing them to renovate. "What we are starting to see in Sea Pines is people buying the older ones and tearing them down," Skrip says. "They have built beautiful homes." Central Plantation features single-family homes and villas with direct access to golf courses, while homes in Calibogue Cay offer deep water views and have private docks so boaters can reach the Intracoastal Waterway. Club Course is one of the few sub-communities with primarily full-time residents. Along the beach, 5,000-square-foot custom mini-mansions cost between $5 and $10 million, with a couple of homes priced close to $16 million. Homes a few rows back from the beach cost between $1 and $5 million, and a couple of villas cost between $600,000 and $900,000. The Beaufort County School District scores an overall A-minus on Niche and serves nearly 22,000 students. Hilton Head Island Elementary School scores an overall B-plus on Niche, while Hilton Head Island Middle School earns a B and Hilton Head Island High School scores an A-minus. The high school has various clubs, including book, debate and pep clubs. Sea Pines is also home to the oldest Montessori school in the state, Sea Pines Montessori Academy. The school serves students through eighth grade, offering robust art, music, Spanish and fitness programs. And since it's so close, locals often bike their kids to school. "I remember when I lived in Sea Pines and my daughter was little, we would take her to school on the bike," Iredell says. Some of the land that Fraser preserved when planning the community included the Sea Pines Forest Preserve. The preserve has 8 miles of hiking trails that cut through and around dense forests, marshland and wildflower meadows. "The forest preserve is one of the most underrated and underutilized things in this whole neighborhood; it's one of my favorite things," Skrip says. "There's never anyone down there. It has beautiful lakes, places to sit and you can walk for days." Plus, the preserve's pavilion is available to rent. "I've got a friend that rents the pavilion every year and hosts an oyster roast for her clients." A lot of locals spend their time on the water. The South Beach Marina juts into Braddock Cove, where kayakers and local anglers explore the water or cast a line. From the marina, locals can quickly access the beach. At Tower Beach Club, only Sea Pines residents have access. "You'll hear people call it Owner's Beach," Skrip. "It's nice when other beaches are busy on days like the Fourth of July. You can come here, and it won't be as busy." Harbour Town is another popular spot to access the water. The Harbour Town Yacht Basin offers watersports from parasailing to paddleboarding, and locals can hop on a year-round cruise or a private fishing charter. The Harbour Town Pier stretches into the Sound and offers panoramic views of the Yacht Basin and the iconic red and white lighthouse. Harbour Town also features the Harbour Town Golf Links, home of the RBC Heritage Tournament. The PGA Tour signature event is one of the biggest on the Island, bringing over 100,000 folks to Sea Pines. The charity event has been a community hit since it started in 1969. "My husband and I would always ride bikes over to the Heritage event when we lived here," says local Realtor Debbie Iredell of RE/MAX Island Realty. Each game culminates at the 18th hole, where the Calibogue Sound and flanking marshes are most visible. Heron Point and Atlantic Dunes offer additional golfing options. Racquet courts are available across Sea Pines. In South Beach Racquet Club, pickleball and tennis courts are filled with people throughout the day. Adult tennis programs, clinics and drills are available to club members. Harbour Town is the hub of all things dining and shopping. Locally owned shops and boutiques surround the Yacht Basin, from Fresh Produce and Coastal Treasures to Radiance Women's Boutique. Music from restaurant patios pours into corridors, and ukelele players strum on the sidelines by the water. Bright red Adirondack and rocking chairs scatter the shopping quarter, often picked up by those looking to rest their feet. And vacationing families walk around with melting ice cream cones in hand. Local Ginevra Boyes co-owns a Harbour Town business, Honey and Thistle, and enjoys getting to live and work in the area. "It's like living on vacation here," Boyes says. "I have a villa right on the harbor, and several bars are within crawling distance." Quarterdeck sits right by the pier, offering views of the Sound while locals enjoy oysters and a beer or glass of wine. The Crazy Crab provides seafood favorites, from lobsters and crab legs to grilled salmon and a classic Lowcountry shrimp boil. The Salty Dog at South Beach offers seafood pot pie, shrimp and grits and a crab cake platter. A Harris Teeter sits just outside the gates in Park Plaza. Hilton Head is a barrier island, so flood risk is high. According to Risk Factor, Sea Pines has extreme flood and air factors based on the presence of hurricanes. Since it's located along the water, most locals have or are required to have flood insurance. Evacuation routes are in place, and the community comes together in cases of emergencies. Locals primarily use bikes and golf carts to shuttle across the resort. The community also offers a trolley service that operates until one in the morning. It reaches areas like South Beach and Harbor Town. When leaving the Island, Business 278 is the only way off. The highway can get congested occasionally, and locals mostly avoid crossing the bridge on Saturdays. Hilton Head Island Airport is about 10 miles from Sea Pines, serving American Airlines, Delta and United. Hilton Head Hospital is about 6 miles away.

Windmill Harbour's luxury townhomes and million-dollar estates center around the largest inland marina on Hilton Head Island. Lined with 70-foot yachts and 30-foot sailboats, the 15-acre yacht basin is well-protected by one of the East Coast's only three harbor lock systems. "It's obviously a great place if you love yachts and boating, but you don't have to own one to live in Windmill Harbour," Maria Skrip says. Local broker and co-owner of RE/MAX Dream, Skrip, says, "It's home to the South Carolina Yacht Club; let's just say you're not a boater, that's okay, you can just utilize the pool and clubhouse." "They actually have a pretty good mix of people there," Skrip adds. "You have some younger single people, families with young kids and some retirees."   Driving through the gates, "you're going to first hit a stop sign and either go right or left," Skrip says. "If you go right, that'll take you to the yacht club and all the amenities," and "If you take a left, you're winding around the harbor and out towards the lock system." Tree-canopied streets wind around the neighborhood, showcasing an array of grand homes, most of which feature Charlestonian-style architecture. There are pastel-colored villas, waterfront single-family homes and townhomes "the size of houses," Skrip says. "I mean, basically, the townhomes are 3 stories tall with stucco exteriors; most even have elevators." These go for around $1 million to $2 million. "The villas or little condos are right where the yacht club is," she says. They can range from $425,000 to $650,000. The single-family homes "have all been custom built," she adds, "so you get a variety of styles." There are contemporary farmhouses, craftsman-style bungalows and cape cods, too. The homes further inland typically range between $700,000 to $900,000, while the waterfront estates can list over $2.5 million. Tree-covered brick walking paths loop around the whole neighborhood, connecting to all the resort-style amenities. While a membership isn’t required for property ownership, the South Carolina Yacht Club serves as a central part of the community where neighbors meet up for weekly tennis practice and catch up by the Olympic-sized pool. It offers a few youth programs too, including Hilton Head Island’s premier junior sailing course. Residents launch kayaks, cast fishing lines and watch the sunset off the community fishing pier. Thanks to a new heating and cooling system, the community pool stays open all year long. There might not be a golf course in Windmill Harbour, but all residents have access to 6 top-tier courses across the island. Each May, Windmill Harbour hosts the Hilton Head Island Boat Show. A variety of marine-themed vendors surround the large yachts, colorful sailboats and decked-out motorboats displayed around the marina. Windmill Harbour gives each resident two free tickets to the Island’s most exclusive Boat Show. At the South Carolina Yacht Club, locals can eat lunch poolside, spend happy hours at the bar and head to the dining room afterwards for a steak dinner. A homestyle brunch is served every Sunday, too. Leaving the marina, boaters can turn left to order the Southern seafood boil at The Crazy Crab or make a right to enjoy a more upscale meal with a view at Sunset Grille. A Publix Supermarket, Walmart and other chain retailers are less than 5 miles down the road. Windmill Harbour is zoned for the Beaufort County School District. Hilton Head Island Early Childhood Center scores a B on Niche. Hilton Head Island Elementary scores a B-plus and Hilton Head Island Middle gets a solid B. Hilton Head Island High receives an A-minus and offers an International Baccalaureate Diploma Programme. Windmill Harbour sits immediately across the J. Wilton Graves Bridge at the gateway to Hilton Head Island. US Route 278, otherwise known as William Hilton Parkway, runs along the neighborhoods north border. The highway takes residents about 10 miles south to the coastal beaches and 7 miles north to Downtown Bluffton. Travelers can easily get to the Hilton Head Island Airport or drive 40 miles south to arrive at Savannah/Hilton Head International Airport. Besides boats, cars are the most common form of transportation here. While beach parking can be expensive and hard to find during the summers, locals can head to the Island’s website and apply for a resident beach parking permit.

Indigo Run is central to everything Hilton Head Island has to offer. The gated community sits right in the middle of the Island between U.S. Highway 278 and Marshland Road, just 10 miles from both the mainland and oceanfront beaches. Although it's one of the only communities without a coastline, Indigo Run still offers covetable Lowcountry views. John Robinson, a local Realtor of 17 years with Dunes Real Estate, says, "It's a big deal to have a nice view in Hilton Head," and Indigo Run offers "some of the best on the Island." While they're not oceanfront, "most of the homes have a pretty view from the backyard – lakes, ponds, lagoons and lots of golf course views," he says. Hilton Head Island's newest golf course weaves through the southern half of Indigo Run. Built by Jack Nicklaus and his son in 1995, The Golf Club at Indigo Run spans 6,700 yards of Lowcountry landscape lined with tall pines to protect homes from flying golf balls. The course is only open to residents with full Golf Club memberships. Those with the required social membership can use The Club's Har-Tru tennis and pickleball courts or relax by the Junior Olympic-sized pool. There's also a 2,300-square-foot fitness center available in the central Clubhouse. Anyone can pay to play at the Golden Bear Golf Club. "It's a public course that's well taken care of and really a pleasure to play," Robinson says. A wooden boardwalk loops around the man-made lake at Jarvis Creek Park, winding through a canopy of Carolina pines. At the park, residents can fish for largemouth bass off the pier or visit the shaded playground. Coligny Beach is only 6 miles away via the back gate along Marshland Road. The homes in Indigo Run typically feature new traditional ranch-style architecture with protruding two- to three-car garages and modern interiors reminiscent of the early 2000s. The properties on the community's south end back up to The Golf Club's private course, while the north side borders the public Golden Bear Golf Club. Regardless of location, most single-family homes cost between $1 million and $1.7 million in Indigo Run. However, those off the private golf course can go for around $800,000. Some two-bedroom condos are available on either end of the community in the Summer House and Avalon Villas subdivisions. These listings range from $300,000 to $475,000. Indigo Run's mid-Island location makes it easy for residents to find groceries, local shops and restaurants. Publix Supermarket anchors the Festival Centre at Indigo Run. Shoppers can walk to Corner Perk, order a latte, or pick up an easy dinner from New York City Pizza. Household essentials are just across the parking lot at Walmart Supercenter. Immediately north of the community, Port Royal Plaza features a variety of local restaurants. There's crab Rangoon at OKKO Japanese, house-made noodles at JINYA Ramen Bar and classic Southern-style breakfast platters at Plantation Café & Deli. Residents head to Frankie Bones for brunch on Sundays after church. Next door, Main Street Village is packed with over 30 upscale boutiques and more local restaurants. Indigo Run is just across the highway from some of the best public schools in Beaufort County. Hilton Head Island Early Childhood Center offers a preschool through kindergarten program that earns a B on Niche. Hilton Head Island Elementary scores a B-plus, Hilton Head Island Middle gets a B and Hilton Head Island High receives an A-minus. The high school broke ground on a new three-story classroom wing in May 2024. Indigo Run sits in the mid-Island region between U.S. Highway 278 and Marshland Road.  Also known as William Hilton Parkway, Highway 278 loops around the Island and connects to the mainland in about 5 miles. Hilton Head Hospital and the local airport are only a few miles north of the community, and the oceanfront is less than 6 miles southeast. Every neighborhood on Hilton Head Island is at a higher risk of flooding than its mainland neighbors, but Robinson says Indigo Run is a bit more protected than some of the other Island communities. "It's further inland, so it's not like you're on the coastline. Although even if you're in an oceanfront community, I've lived here for 34 years, and I've never seen any problems with storms really affecting the coastal neighborhoods." He adds, "We're just off the Gulf Stream, so we get pretty lucky with hurricanes here."

Port Royal Plantation isn’t just a neighborhood, it’s a lifestyle. Residents can walk out their back door and step onto one, maybe even two, of the highest rated golf courses in the South. After a sunny morning on the fairways, golfers ride over to the clubhouse for lunch. Interlocking bike trails connect to the new community beach house, where residents can lay by the pool or follow the private boardwalk down to the ocean. While large resorts and tourist destination are just around the corner, Port Royal Plantation maintains it’s quiet, sophisticated charm year-round. A local broker and co-owner of RE/MAX Dream, Maria Skrip says, “It’s one of the only gated oceanfront communities on Hilton Head Island that doesn’t allow short-term rentals, so it’s not a place for vacationers – this is where the locals live.” A gated entrance with 24/7 security staff ensures that Port Royal Plantation’s single-family homes remain secure, even when homeowners are away. Most of the residences date back to the 1970s, ‘80s and ‘90s, but there are some New Traditional Victorians from the early- to mid-2000s. One-story prairie and ranch-style homes feature low-pitched roofs with defined horizontal lines. Full front porches invite residents into Cape Cod-style cottages while the New Traditional Craftsman homes offer paved pathways leading straight to the front door. Tall Carolina pines and sturdy live oaks form a natural wall around most homes. This creates a peaceful sense of seclusion while at the same time protects homes from flying golf balls. These listings begin around $900,000 for an older three bedroom and go up to $2.25 million for a five-bedroom built in 2022. Similar-style homes with oceanfront views and private beach access fall within the $3 million to $5 million range. Port Royal Village has condo-style villas and two-story townhomes for $450,00 to $725,000. As of 2024, Port Royal Plantation’s annual POA dues totaled around $3,800. “When you’re paying that fee, you’re paying for the 24/7 security gate, the pool area, the gorgeous restaurant and all those kinds of amenities,” Skrip says. The golf course is open to the public for membership, “so that’s why your annual fees aren’t as high here.” Though anyone can become members of The Port Royal Golf and Racquet Club, one of the two 18-hole golf courses is reserved every morning for member-residents only. Locals meet up for regular practices at the clay tennis and pickleball courts just outside the central clubhouse. A fenced-in community garden with 78 individual plots rests along the inland marshes. In 2020, neighborhood residents came together to fund a community Beach House located right on the oceanfront. It features an Olympic-sized pool, a small playground and a private boardwalk leading down to the beach. After a morning on the golf course, Club members stop by Robber's Row Grille to eat fresh tacos under the shade of a veranda. Port Royal Plaza is packed with all types of restaurants right across the highway. There’s classic American bar food at Street Meet, specialty pasta at Bella Italia Pizza and made-to-order hibachi at OKKO Japanese. Residents regularly stop by Plantation Café & Deli to order their signature crab cake eggs benedict. About 5 miles down the road, Shelter Cove Towne Center has clothing boutiques, more independent restaurants and the local Kroger, too. Port Royal Plantation is only 5 miles away from some of the best schools in Beaufort County. Hilton Head Island Early Childhood Center offers a preschool through kindergarten program that scores a B on Niche. Hilton Head Island Elementary earns a B-plus, while Hilton Head Island Middle receives a solid B. Hilton Head Island High School gets an A-minus and offers the International Baccalaureate Diploma Programme. Coggins Point Road cuts through the center of Port Royal Plantation and connects to US Highway 278 just past the gates. Locally known as William Hilton Parkway, Highway 278 links to the central oceanfront in fewer than 10 miles. Residents can follow the road about 10 miles northwest to reach the mainland. Hilton Head Hospital and the Hilton Head Island Airport sit fewer than 5 miles away from the neighborhood. The airport “is bigger than a commuter airport, but it’s mostly smaller planes so there’s not a lot of noise,” says Christopher Skrip, a local broker and co-owner of RE/MAX Dream. Port Royal Plantation sits at the northeast point of Hilton Head Island, where the Port Royal Sound meets the Atlantic Ocean. This makes the community especially vulnerable during hurricanes and other large storms. According to Risk Factor, Port Royal Plantation is at extreme risk of flooding and wind damage. The neighborhood’s email blast system alerts residents of any potential storm threat and provides evacuation route details.

Artfully designed homes, top-rated Lowcountry recreation and a central location make Wexford "one of the premier private club communities on the East Coast," Steve Timperman says. A current Wexford resident and Realtor with Charter One Realty, Timperman says its 37-acre central harbor is a huge selling point for homebuyers. "We have one of the only two locked marinas on the Island, and it's completely tidal-controlled, so you don't have to worry about hurricanes really ever here." The iconic golfer and course architect Arnold Palmer designed the world-class golf course winding through the neighborhood. "We also have around 40 or 50 great shops and restaurants within a mile of our gate," Timperman adds. Plus, Hilton Head Island's sugar-sand beaches are only a 3-mile bike ride away. Most of the homes in Wexford sit on well-maintained half-acre lots behind a gate with 24/7 security on staff. These houses feature New Traditional architecture with "British West Indies and Colonial influences," Timperman says. Grand staircases lead to front porches lined with stately columns, while backyard verandas overlook the marina, marsh or golf course. Inside, Cathedral ceilings and long windows allow natural light to flood the breezy open floor plans. As one of the most sought-after gated communities on the Island, Wexford homes typically don't sell for anything less than $1.5 million. Some with over 7,000 square feet can get up to $3.75 million. Along with the listing price, homebuyers must pay a $50,000 initiation fee and $20,560 in annual POA fees. Half acre RV lots and some two-bedroom villas list between $250,000 and $350,000 just outside the gates. Wexford is home to some of the Lowcountry's finest outdoor recreation. Residents can walk out their back door and sail into deep water canals leading into the Intracoastal waterway. The Harbour Center has kayaks and paddleboards for the community. Whether it's a humid day in July or a mild winter day, members of Wexford Yacht Club can swim in one of the two temperature-controlled pools. Local professionals hold regular clinics and one-on-one training sessions on the Club's Har-Tru clay racquet courts. Wexford's golf course features fairways lined with moss-draped oaks and holes overlooking saltwater marshes, perfectly demonstrating Arnold Palmer's philosophy of preserving the natural landscape. Residents can bike to Crossings Park and ride through dirt trails shaded by tall pines. Its three ballfields host community youth baseball league practices in the spring. Next door, Bristol Sports Arena has a skate park and an outdoor hockey rink. The annual Yacht Hop is one of the most anticipated events of the year in Wexford. Each May, residents and guests dressed in white and gold walk from boat to boat, eating hors d'oeuvres and sipping cocktails along the way. The event concludes with a live auction where attendees can bid on exclusive experiences and vacations. All the funds raised are donated to the local non-profit Hospice Care of the Lowcountry. Wexford is just a bike ride away from some of the hottest restaurants and retailers on Hilton Head Island. Residents head outside the gates and immediately arrive at The Village of Wexford. The walkable, upscale shopping center features classy coastal wear at boutiques like Evelyn & Arthur and one-of-a-kind kid's clothes at the Island Child. Locals rave about the specialty coffee and casual Mexican fare at the Java Burrito Company. For a special occasion, they book reservations for dinner and a show at The Jazz Corner, but most Friday nights are spent catching up with neighbors at the British Open Pub. Hinoki Japanese serves sushi and sake, and Nunzio Restaurant + Bar offers locally sourced Italian cuisine along New Orleans Road. Around the corner, residents can order moonshine flights or try the award-winning shrimp and grits from A Lowcountry Backyard Restaurant. The local Publix is right across the street. Wexford is fewer than 8 miles from some of the best public schools in Beaufort County. Hilton Head Island Early Childhood Center offers a preschool through kindergarten program that earns a B on Niche. Hilton Head Island Elementary scores a B-plus, Hilton Head Island Middle gets a B and Hilton Head Island High receives an A-minus. The high school broke ground on a new three-story classroom wing in May 2024. Locally known as William Hilton Parkway, U.S. Highway 278 wraps around Wexford's south and east sides. Its loop shape makes it easy to get anywhere on Hilton Head Island. Residents can follow Highway 278 about 7 miles north to access the local hospital and the Hilton Head Island Airport. Across the J. Wilton Graves Bridge, the route continues onto the mainland and links to Historic Bluffton in around 15 miles.