The Most Unusual Private Islands Ever Sold
Private islands have always represented the ultimate luxury purchase, but some sales stand out for reasons that go far beyond pristine beaches and crystal-clear waters. From abandoned castles with murky wartime rumors to properties won in poker games, these islands come with stories that sound too wild to be real.
Over the years, the global private-island market has seen some extraordinary transactions — each with its own peculiar twist.
Darby Island (Bahamas)
Sitting in the Exuma Cays, this 554-acre paradise comes with an 8,000-square-foot abandoned castle and one of the strangest backstories in real-estate history. Before and during World War II, the island belonged to Sir Guy H. Baxter, a British hotelier allegedly sympathetic to the Nazis.
According to local legend, he may have used the castle’s rooftop to signal German submarines prowling the Atlantic. Elderly residents recall seeing strange flashes of light from the building during the war, and the island’s cave network supposedly provided refuge for subs. The property later hit the market for $39 million, complete with 14 beaches and a disused airstrip now reclaimed by nature.
Skorpios Island (Greece)
This 74-acre Greek paradise became world-famous after shipping magnate Aristotle Onassis married Jackie Kennedy there in 1968. Its fame drew attention from Bill Gates, Giorgio Armani, and Madonna — none of whom succeeded in buying it.
In 2013, Ekaterina Rybolovleva, daughter of Russian billionaire Dmitry Rybolovlev, leased the island (and nearby Sparti) for about €100 million (~$131 million). Under Greek law, ownership remains with the Onassis family trust, making this one of the most high-profile long-term leases in island history.
Red Rock Island (USA)
The only privately owned island in San Francisco Bay, this reddish rock near the Richmond–San Rafael Bridge has a backstory fit for a Western. Legend says it was won in a bet in the 1800s, and no one has lived there since the 1850s.
The 5.8-acre outcrop offers panoramic views of the Bay Area but is legally undevelopable due to environmental restrictions. It was last listed in 2024 for $25 million, attracting interest from buyers as far as Miami and New York.
Lanai (Hawaii, USA)
Oracle co-founder Larry Ellison didn’t just buy a private island — he bought 98% of Hawaii’s sixth-largest island, Lanai, from Castle & Cooke’s David Murdock in 2012 for an estimated $300–$500 million. Home to roughly 3,200 residents, two Four Seasons resorts, and miles of pineapple fields, Ellison’s purchase aimed to revitalize the island’s economy through sustainable infrastructure rather than create a personal playground.
Necker Island (British Virgin Islands)
Richard Branson’s famous retreat started as a bargain buy that turned into a global icon. The Virgin Group founder purchased the 74-acre island in 1979 for just £180,000 and transformed it into a Balinese-style luxury resort now valued at around $100 million.
Guests have included Princess Diana, Barack and Michelle Obama, and countless celebrities, paying hundreds of thousands per week for exclusivity.
Little Saint James (U.S. Virgin Islands)
Few islands carry as much infamy as this 70-to-78-acre property once owned by Jeffrey Epstein, who bought it in 1998 for $7.95 million. By 2019, it was worth nearly $64 million and had become notorious as the site of his criminal activities.
After Epstein’s death, both Little Saint James and neighboring Great Saint James were listed for $125 million. In 2023, billionaire Stephen Deckoff purchased both for $60 million, reportedly with plans to convert them into luxury resorts.
Sanda Island (Scotland)
Off the southern tip of Scotland’s Kintyre Peninsula lies a 453-acre island complete with seven houses, a lighthouse, a pub, and a thriving seal colony. It was sold in 2010 for around £2.5 million to new private owners.
The estate also includes two smaller islets, Sheep Island and Glunimore Island, and is one of the few private islands that functions as a small community rather than just a retreat.
Shuna Island (Scotland)
At 1,100 acres, Shuna Island is both tragic and romantic. New Zealand explorer George Buckley, fresh from Ernest Shackleton’s Nimrod expedition, built Shuna House — often mistaken for a castle — in the early 1900s.
According to local lore, the architect he hired died on the Titanic in 1912 while en route to sell similar designs in America. The grand house was occupied until the 1980s and now sits in atmospheric ruins, awaiting restoration.
James Island (Canada)
Off the coast near Sidney, British Columbia, billionaire Craig McCaw turned this 780-acre former explosives-plant site into an exclusive, eco-friendly haven. After buying it for $19 million in 1994, he added a 5,000-square-foot main house, six guest cottages, and an 18-pit Jack Nicklaus-designed golf course.
Gas vehicles and hunting were banned, and power lines buried underground. When the dot-com crash dented McCaw’s fortune, he listed it for $75.1 million.
Osea Island (England)
Located in the Blackwater Estuary, Essex, this 380-acre tidal island is reachable only four hours a day via a 2-mile Roman causeway. Once owned by music producer Nigel Frieda, it spans 90 bedrooms and 61 bathrooms across multiple period buildings.
Osea has hosted Stormzy during album production and served as a filming site for The Woman in Black, Jesus Christ Superstar, and HBO’s The Third Day (2020). It was listed for £25 million, among the UK’s most expensive island properties.
Bond’s Cay (Bahamas)
Pop star Shakira, Pink Floyd’s Roger Waters, and Spanish singer Alejandro Sanz reportedly paid $16 million for this 700-acre island about 120 miles off Florida’s east coast. Their vision — an eco-luxury artist’s retreat — captured headlines, but plans have since stalled.
With five beaches and three salt ponds, Bond’s Cay remains an untouched Caribbean dream awaiting its creative rebirth.
Table Rock Islands (Canada)
In Ontario’s Georgian Bay, architect William Grierson designed a solar-powered round house with a central open-air courtyard and 360-degree water views. Anchored into Precambrian rock with 24 concrete columns, the property includes the main island plus five smaller undeveloped islets.
It was listed for CA$2.2 million, a rare fusion of modernist design and rugged wilderness.
Innocence Island (Bahamas)
At 681 acres, this is the largest privately owned island in the Bahamas and one of the few with its own airstrip bearing a unique ICAO code — MYEY. Located in the Exumas, it features 15 miles of nature trails and has had only four owners throughout its history.
When auctioned with a $10 million reserve, that quirky pilot call sign became a surprising selling point for privacy-minded aviators.
Celine Dion’s Île Gagnon (Quebec, Canada)
Not every dream island has palm trees. The legendary singer built a French-Norman-style mansion on Île Gagnon in Laval, set amid the Rivière des Mille Îles.
The gated bridge entrance added fair-tale charm to the wintery setting. Dion sold the property in 2016 for C$25.5 million (≈ US$19 million), proving that even superstar retreats evolve with time.
From Wartime Secrets to Modern Escapes
The private-island market has evolved from vacation hideaways into showcases of ambition, eccentricity, and occasional folly. These 14 sales prove that the most fascinating properties aren’t always the biggest or most expensive — sometimes it’s the rumored spy castle, the Titanic-linked architect, or the celebrity art colony that makes an island unforgettable.
Whether driven by privacy, investment potential, or pure bragging rights, buyers continue to spend millions for their own slice of paradise — each adding another chapter to the bizarre history of private-island ownership.
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