At the southern-most tip of Rhode Island, on a peninsula jutting out to Long Island Sound, sits the quiet hamlet of Watch Hill, an idyllic enclave within the borders of Westerly. Like Newport on the other side of the state, Watch Hill once attracted Hollywood and American royalty of the Gilded Age, who took up seasonal residency in summer cottages and grand hotels here, including the iconic Ocean House — today, a luxury hotel with a private beach, croquet grounds, bars and terraces overlooking the Sound, and fine dining, including a renowned, decadent Sunday brunch.

Nearly as iconic to Watch Hill’s coastline as Ocean House is the “High Watch” estate, aptly named for its elevated position high above a private beach and protected by a formidable sea wall that looks like it could ward off an assault by Poseidon himself.

Known as “Holiday House” when it debuted in 1930, the grand and stark-white colonial was built by the Harkness family, heirs to the Standard Oil empire, and for nearly 30 years was one of the homes of philanthropist Rebekah Harkness. Harkness was somewhat notorious for having spectacular parties at the mansion, with guests lists that included the rich, famous and wildly eccentric.

Musician Taylor Swift bought the property in 2013, reportedly paying $17.75 million in cash. And the singer has held her share of celebrity-brimming affairs at High Watch, including 4th of July festivities.

Locals refer to the house as Holiday House, High Watch or the Harkness House. Swift gave a nod to its original name in her song “The Last Great American Dynasty,” from the album Folklore. The song pays tribute to the house and to Rebekah Harkness, with whom Swift feels a sense of kinship. Both of the women “made waves” with the neighbors.

In a March 2021 interview with People Magazine, Swift said she was particularly proud of the song, especially the lyrics: She had a marvelous time ruining everything.

“Because it’s about what happens when women step out of their cages and run,” she explained.

“It can be a real pearl-clutching moment for society when a woman owns her desires and wildness,” the Grammy-awarded megastar told the magazine. “And I love the idea. That the woman in question would be too joyful in her freedom to even care that she’s ruffling feathers, raising eyebrows or becoming the talk of the town. The idea that she decided there were marvelous times to be had, and that was more important.”

In 2019, during an appearance The Ellen Show, Swift told the host that her favorite place to holiday is Rhode Island.

WATCH HILL’S LEGACY CARRIES ON

Holly Powell knows Watch Hill from two perspectives: She grew up in Watch Hill, and today, she’s a Realtor with the Westerly office of Berkshire Hathaway’s New England Properties, licensed in both Rhode Island and Connecticut. Powell describes Watch Hill as “an exclusive, but understated waterfront community.”

Many of the homes are fashioned in “quintessential New England architectural styles,” Powell said. When they come to market, single-family homes can sell for up to $10 million, depending on the setting and amenities. The 2010 census estimated Watch Hill’s population at just 154 full-time residents.

Watch Hill is a private community, not by gates and guards, but by geography. “There’s one road in and one road out,” Realtor Holly Powell pointed out. It has an eternally charming historic district recognized by the U.S. National Register of Historic Places.

Watch Hill’s legacy is one of summer cottages and generational homes. There are residents who live there year-round, of course, but many of residents who come to Watch Hill for weekend or summer getaways now stay longer, especially in the wake of COVID-19, when telecommuting and teleconferencing became “the new normal.” Besides, it’s just two hours from Boston, three hours to New York City, and less than an hour and half to Hartford.

“Being able to work from home today changes the landscape of what a buyer is looking for,” Powell said. “They want a comfortable office space and a view. They also want comfortable spaces to enjoy with family and friends.”

“Gads of money” has come into the neighborhood in recent years, to acquire homes when they come to market, and to renovate them according to the new homeowners’ design preferences, the Realtor said.

“They want to create their own bespoke home to leave to their heirs,” she suggested. “Watch Hill has some of the most magnificent beaches. That is what’s drawn people here for centuries.”