The Billionaire's Hideaway: 10 Famous People Who Own Homes On Nantucket Island

Nantucket Island, Massachusetts, remains the ultimate symbol of quiet, old-money luxury on the East Coast, and as of late 2024, its roster of high-profile residents is more star-studded than ever. Unlike the flashier Hamptons, Nantucket is a haven known for its strict architectural preservation, cobblestone streets, and a fiercely guarded culture of privacy, making it the perfect retreat for A-list celebrities, political heavyweights, and Wall Street titans looking to escape the spotlight. The island’s appeal lies in its understated elegance, where multi-million dollar shingle-style estates are tucked away in secluded neighborhoods, allowing famous residents to enjoy the coastal lifestyle without the constant presence of paparazzi. The recent surge in record-breaking real estate deals, including the sale of the state's most expensive residential property, solidifies Nantucket's status as a billionaire's playground.

A-List Owners and Frequent Visitors: A Nantucket Celebrity Roster

The list of notable figures who own property or are frequent summer visitors to Nantucket is extensive, often blending Hollywood stars with political and business magnates. These individuals typically seek the island for its seclusion and the casual, low-key atmosphere that New Englanders are known for, where celebrities are often treated with polite indifference.

Notable Nantucket Homeowners and Frequent Guests:

• Dave Portnoy: Founder of Barstool Sports. Known for purchasing the island's most expensive residential property.
• Kourtney Kardashian: Reality television star and media personality. Owns a highly desirable vacation home in the Pocomo neighborhood.
• Tommy Hilfiger: Iconic American fashion designer. A long-time and prominent homeowner on the island.
• Ben Stiller: Emmy-winning actor, comedian, and filmmaker. Has been a long-standing property owner, often spotted on the island with his family.
• Amy Poehler: Acclaimed actress and comedian. Known to own property and spend summers on the island.
• John Kerry: Former U.S. Secretary of State and Senator. A long-time political figure with deep ties to the island.
• Joe Biden: Current U.S. President. Has a history of visiting and vacationing on the island, often staying in high-profile rental properties.
• Meghan Trainor: Grammy-winning singer-songwriter. A native of Nantucket, she maintains strong ties to the island.
• Bill Gates: Co-founder of Microsoft and one of the world's richest individuals. Reported to own property on the island.
• Max Weinberg: Long-time drummer for Bruce Springsteen's E Street Band and former bandleader for Conan O'Brien. A known property owner.
• Steven Cohen: Billionaire hedge fund manager. Owns lavish property in the Pocomo area.

The Record-Breaking Real Estate Transactions That Define Nantucket Luxury

Nantucket’s real estate market is notoriously exclusive, with median home prices soaring well into the multi-million dollar range. In recent years, high-profile transactions have cemented the island's status as the most expensive residential market in Massachusetts, driven primarily by the desire for waterfront access and unparalleled seclusion.

Dave Portnoy's Historic $42 Million Purchase

The most talked-about celebrity real estate deal in recent Nantucket history was the acquisition by Barstool Sports founder Dave Portnoy. Portnoy reportedly purchased a massive waterfront estate along Nantucket Harbor for an astonishing $42 million (some reports cite $44 million), setting a new residential real estate record for the entire state of Massachusetts. The property is a sprawling 1.2-acre harborfront home, epitomizing the scale of wealth now pouring into the island. This purchase signifies a shift, with new-media moguls joining the ranks of established Wall Street and fashion magnates who have traditionally dominated the island's high-end property ownership.

The Kardashian Family’s Pocomo Peninsula Retreat

Another significant celebrity presence is the Kardashian family, specifically Kourtney Kardashian, who owns a spectacular vacation home. Her property is situated in the highly desirable Pocomo neighborhood, a secluded peninsula on the eastern side of the island known for its privacy and stunning water views. The home is described as a classic New England shingle-style estate, reflecting the island’s commitment to traditional architecture, despite its massive reported value. The presence of such a high-profile reality TV star underscores the growing appeal of Nantucket's quiet luxury to a younger generation of media celebrities.

Other Notable Nantucket Real Estate Movements

The island's real estate market is constantly shifting, even for the famous. In recent news, former New England Patriots coach Bill Belichick sold his charming Nantucket beach cottage. The sale, which occurred at a hefty discount, highlights the dynamic nature of luxury property ownership on the island. Furthermore, an equestrian estate that once hosted global superstars Beyonce and Jay-Z was recently listed, demonstrating that even rental properties on Nantucket command A-list attention and prices, often becoming the most expensive listings in the tony area.

The Nantucket Lifestyle: Why Celebrities Choose Seclusion Over Spotlight

What truly sets Nantucket apart from other luxury destinations like Martha’s Vineyard or the Hamptons is its deep-rooted culture of privacy and discretion. This is, in fact, the primary reason why so many famous people, from actors like Ben Stiller and Amy Poehler to political figures like John Kerry and Joe Biden, choose to spend their summers here.

The Value of Discretion

On Nantucket, the prevailing attitude among locals and long-time residents is one of casual respect for personal space. New Englanders are renowned for treating celebrities more casually and politely, meaning there is minimal paparazzi presence and little public fuss over a sighting. This allows people like Ben Stiller to walk the streets of downtown without being constantly swarmed, or for billionaires like Steven Cohen to manage property renovations without excessive public scrutiny from outside the local Historic District Commission.

A Haven of Old-World Charm

The island is dedicated to preserving its historic charm. The architecture, dominated by gray-shingled homes and manicured hedges, provides a natural barrier to the outside world. Neighborhoods like Sconset and the secluded areas near Wauwinet offer vast estates with private beaches and deep-water moorings, ensuring that high-net-worth individuals can truly "get away." The island's focus on its summer tourist economy and its centuries-old history—with famous visitors dating back to Herman Melville—means the local infrastructure is built to cater to an elite, yet discerning, clientele. The constant flow of Wall Street CEOs, tech founders, and media personalities ensures that Nantucket remains a discreet power hub. It is a place where wealth and fame converge not to be seen, but to simply *be*, enjoying the coastal ease and the quiet luxury that only this 14-mile-long island can offer.