Luxury Custom Homes in Kiawah, SC

My most vivid—or at least most fraught—memory of my time at Kiawah Island in the 1990s is the grocery store. During my childhood, my family would vacation at Kiawah each summer. At that time, the nearest grocery store—miles from the island—was Piggly Wiggly, affectionately known as the Big Pig. We would get off the plane in Charleston and drive directly to the grocery store, where my father would announce that we must purchase everything we would need for the whole following week, because he was not wasting the vacation driving 45 minutes back and forth to the Piggly Wiggly.

Thank you for signing up!

By clicking submit, you agree to our <a href="http://observermedia.com/terms">terms of service</a> and acknowledge we may use your information to send you emails, product samples, and promotions on this website and other properties. You can opt out anytime.

This gave grocery shopping a bizarre, Supermarket Sweep-style urgency. We invariably forgot something very basic. This was fine. We mostly ate at the ice cream shop Scoopers, anyway.

In addition to ice cream, I associate Kiawah with boogie boarding, collecting sand dollars on the beach, and being wrongly told to run in a serpentine pattern if chased by an alligator. There is an alligator in every lagoon. The summer was very fun. It was not very glamorous.

Now, if people associate Kiawah with anything, it’s PGA Championships at the Ocean Course, influencer weddings at the Sanctuary Hotel and Johnny Hilbrant sketches, the viral bits in which his “PE Guy” lampoons private equity for an audience largely made up of the people he’s mocking. Ask around and you’ll hear about Uber drivers who picked up unassuming couples from dinner in town, got $5,000 cash tips, and only later learned their passengers were early Amazon executives. In 2015, former Comcast Corp. CFO Michael Angelakis paid $20 million for an oceanfront house, a record for the island at the time. Former President Biden even lists the island as one of his favorite vacation spots. The last fact can perhaps be credited to Scoopers, now sadly closed (RIP, little ice cream shop). The rest of the items represent drastic change over the past 30 years. How a buggy, half-built golf development became one of the priciest addresses in the South is a story of foreign money, a hurricane, a bankruptcy and a great many very well-protected trees.

For three centuries, the island in the Lowcountry on the coast of South Carolina was mostly farmland. English settlers arrived in the 1600s, met a Native American tribe known as the Kiawah and began building there in 1670. Afterward, the island passed among prominent families and, at one point, belonged to the pirate Captain George Raynor. Its economy ran on cotton and logging. Then, in 1974, the island was bought from the C.C. Royal family by the Kuwait Investment Corporation, which quickly began developing it into a luxury resort with world-class golf and a residential community. By 1984, the island was estimated to be one-third complete, with 1,500 units built. Villas on the island ranged in price from $100,000 to $400,000 (approximately $321,000 to $1.3 million in today’s dollars). At the time, this seemed fairly luxurious. The Associated Press called the developing resort town “a stately pleasure dome.” The median home price of a home on Kiawah now hovers around $3.6 million, though that figure is skewed by the island’s numerous villas and condos. A single-family home will run you about $14 million to $25 million, depending on the view.

In 1988, the island changed hands and was purchased for $105 million by the Kiawah Resort Associates, which was an inauspicious time to invest, as Hurricane Hugo, which devastated Charleston, struck the next year. Trees came down and communication was non-existent for several days, but rather miraculously, “the hurricane seemed to skip over the island.” Around that time, the assets were sold to Gerald Barton’s Landmark Land Company, which commissioned Pete Dye to build the now-famous Ocean Course, specifically for the 1991 Ryder Cup. That iteration of the Ryder Cup, known most fondly as the “War by the Shore,” got its name from a Golf World cover. An American team still riding Gulf War fervor, down to camouflage caps, played amid rowdy home crowds and open feuding with the Europeans, on a course where the Atlantic wind punished both teams equally. The course is now rated one of the world’s greatest. Landmark did not get to enjoy it. Barton, an Oklahoma lawyer who had never really taken up golf, had rushed the course through a hurricane onto land that was swamp three years earlier. Two weeks after Bernhard Langer’s missed putt handed the Americans the Cup, federal regulators seized Landmark’s bank, a savings and loan the government itself had once asked him to rescue. What followed included a Japanese bidder the regulators left waiting for a year and a Dallas hotel ballroom crowded with Wall Street bidders. Landmark went bankrupt, and in 1993 the resort went to Bill Goodwin, a Richmond, Va., businessman who had never run a luxury hotel. Goodwin, now a billionaire, and his family still own Kiawah Island Golf Resort, along with the Sea Pines Resort on Hilton Head and the Jefferson Hotel in Richmond.

The Chicago Tribune stated that, afterward, “the island limped along largely unnoticed, drawing a steady stream of regional home buyers but not the top executives and celebrities the island’s managers hoped to attract, until the horrors of overdevelopment elsewhere proved enough of a cautionary tale and sales finally took over.”

This was the Kiawah I knew. Overdevelopment was not a problem in 1990s Kiawah. One vacationer noted in 1993 that “the jumbo-sized snake that had disconcerted us by indolently draping itself over a tree branch at the front door of the nearby cottage” was nowhere to be found. (I recall these snakes and being told that they were “probably harmless” and “not a big deal.” As an adult, I still strongly suspect those words to be lies.) The alligators were still common enough that photos of them were part of town-wide scavenger hunts. Residents whose homes back onto the golf course still know not to let children run loose on the hillier holes, where the elevation can hide a row of alligators sunning themselves on the far slope. The island counts roughly 600 to 700 of them, and the local dogs have not always fared well.

In 1994, the Kiawah Island Inn, at that time the only hotel on the island, “prohibited guests from using flashlights at night because it disorients the sea turtles swimming to shore to lay eggs.” To preserve that wildlife, the Kiawah Island Conservancy (now the Conservancy of the Sea Islands) was established in 1997. They protect 2,273 acres of Kiawah’s 10,000 acres. The town also supports the Kiawah Turtle Patrol, a particularly nice tradition in which islanders help safely shepherd turtle hatchlings from their nests to the ocean. As of 2003, properties could only be built if any removed trees were replanted with approved substitutes. Homeowners complained that this requirement could be a real struggle when they tried to build anything. Still, the trees are beautiful. And the rules weren’t purely sentimental. Every protected acre and replanted oak is land that can’t be built on, which is a fairly reliable way to keep an island exclusive.

More golf courses were built on the island, with the Cassique course opening in 2000. Filming for the movie The Legend of Bagger Vance used the Ocean Course as a backdrop and drew even more visitors to the island. This prompted one reviewer from the Daily Mail to declare the vacation spot “one of the best resorts in the South” while also noting, with unhappy confusion, “they have something down there called the palmetto bug [that] can easily pass for one of our biggest cockroaches.” (They still do, and unlike the sea turtles, it has inspired no beloved traditions.)

The Sanctuary at Kiawah Island, Goodwin’s biggest bet on the island, opened in 2004 and is, as the name might suggest, an Audubon-certified bird sanctuary. The Ocean Course hosted the PGA Championship in 2012 and again in 2021, and is slated to host it a third time in 2031. By the first of those, Presidents George H.W. Bush, George W. Bush and Bill Clinton had all vacationed on the island. Homeowners have included David Falk, the agent who turned Michael Jordan into a sneaker empire (and is credited with coining “Air Jordan”), who kept an oceanfront estate on Surfsong Road; Maria Allwin, widow of hedge fund founder James Allwin, whose house on Flyway Drive put up Joe and Hunter Biden in 2022; and Olympic gold medalist Tara Lipinski, who has a Southern Victorian retreat on the beach. The trees, the birds, or perhaps the gators finally seemed to have dragged in the much-hoped-for celebrity tourists.

In 2013, South Street Partners acquired Kiawah Partners, which included the Kiawah Island Club and Freshfields Village—a spotless shopping center (the only shopping center) with rows of Range Rovers parallel-parked bumper to bumper outside restaurants where you can pour your own wine at $35 an ounce. On summer Fridays, an outdoor concert series draws families of a remarkably uniform complexion who arrive in Lilly Pulitzer and Peter Millar, set out their lawn chairs, open the wine coolers and dance, in near-perfect unison, to cover bands running through Motown and Carolina beach music.

Golf people might date Kiawah’s arrival to the Ryder Cup, and real estate agents to the PGA. Freshfields regulars might not date Kiawah at all. To my mind, however, the full transformation came only in 2013, around the time my parents moved to Kiawah full-time. That was the year a Harris Teeter grocery store opened on the island, in the middle of Freshfields. Truly, the height of glamour.

KIAWAH ISLAND — A South Carolina pastry chef known on the show as “Young Kyle” is seemingly the one to beat on the Food Network’s latest cooking show.

Kyle Caulkins, a 22-year-old pastry cook at The Sanctuary, is one of 10 contestants on the Food Network's “Halloween Baking Championship,” which kicked off Sept. 14. The winner with the creepiest confections at the end of Season 12 takes home a $25,000 grand prize.

Caulkins is one of two Kyles on the show and about 10 years younger than a majority of the other constants, who have been whittled down to six as of Oct. 5. But despite being the brunt of jokes, such as judges asking if he has a permission slip to be there and contestants teasing he needs to go to his room for making a mess at his station, Caulkins is blowing the competition away.

“Yes, I’m young, but if I was the (other) bakers, I’d be a little scared,” Caulkins said.

And rightfully so. He went into the show thinking it would be a “monumental achievement” to beat the other nine players, even at his age. And he did.

The first two weeks of the show, his pastries were named the best of the best by the judges, Stephanie Boswell, Aarti Sequeira and Zac Young.

Caulkins won the premiere Sept. 14 episode for his take on Halloween by creating a pillowcase filled with candy — a childhood trick-or-treat memory he shares with his sister. He won again in week two for his rabid taxidermy deer cake that even had edible foam coming out of its mouth.

The judges called his food a “delight” to eat, saying his work was “beautiful,” “magical” and “delicate.”

On the latest episode, which aired Oct. 5, he created a crumbling castle haunted by vampire cookies — a concoction that earned him a “chef’s kiss” praise.

The praise hasn’t won him any friends.

“I want to beat young Kyle,” contestant Lisa Pak, a home bakery owner in New York, joked on the Sept. 28 episode. “I’m getting tired of him sitting up there.”

In a twist of fate, Caulkins ended up among the bottom bakers on that episode. The challenges centered on Disney themes, where he made a cake showcasing a hero and villain and then a seemingly floating magic mirror made of isomalt. His base for the latter was his famous bonfire bars — an “elevated more adult s’mores experience” he said, with a graham sable bottom, brownie and chocolate chip cookie layers, topped with an orange marshmallow.

Caulkins said growing up in Connecticut, where he lived before moving to the Charleston area, his family always knew he loved making pastries.

In 2023, he graduated from Johnson & Wales University and said cooking school “opened up my world to so many classic techniques I didn’t even know about.”

Now at 22, he’s a pastry chef at the Kiawah Island Golf Resort, which has been rooting him on the entire way.

“Starting this competition as the youngest competitor by almost 10 years, I had to stand up for myself and advocate for me first because I know I have what it takes,” he said. “I want to win and I can achieve whatever I want.”

The next episode of the “Halloween Baking Challenge” airs Oct. 12 on Food Network and the following day on HBO Max.

KIAWAH ISLAND, S.C. (WCSC) — Town officials are considering an ordinance that would create a dedicated conservation fund aimed at protecting land and habitats on Kiawah Island.

The Kiawah Island Conservation Fund would work to shield land from overdevelopment, an issue officials say has affected multiple counties across the Lowcountry.

Town Council Member Lance Spencer said conservation is central to the island’s identity.

“Kiawah has a big focus on living with nature,” Spencer said.

Spencer said the fund would be used to pursue conservation easements and remove land from the development market. He said the focus would likely center on a specific area.

“We’ll probably be more in the Kiawah watershed area, which is more focused on southern Johns Island, which will help with quality of life, water quality, wildlife, air quality, traffic, all the things that make life more enjoyable in this part of the country,” Spencer said.

Collie Farah, a land preservation specialist with the Conservancy of the Sea Islands, said conservation provides tangible benefits to the region.

“Clean air, conservation means clean water, it means food sources, local food sources,” Farah said.

Farah also said the Lowcountry’s natural landscape serves a protective function.

“Produce natural infrastructure against hurricanes and natural disasters, so we depend on the land,” Farah said.

Farah added that the fund’s purpose extends beyond environmental protection.

“We’re protecting culture, a way of life,” Farah said.

If the ordinance passes, the town would establish an advisory board to guide the fund’s decisions.

“We’ll start recruiting board members to be part of that, and we’ve delineated some key qualifications we’d like them to have, so we can make some really informed recommendations,” Spencer said.

The ordinance is scheduled for its second reading on Sept. 1.