4 US Islands With the Most Expensive Homes

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In America, life surrounded by water truly is a something-for-every-budget experience. For example, Zillow lists homes for sale on Smith Island, Maryland, for less than $100,000.

On the other end of the archipelago price spectrum is 10 Tarpon Isle, the only private island in Palm Beach, Florida. Its developers bought it for $85 million in 2021, turned the existing structure into a guest house, built a giant mansion as the main house and added amenities like tennis courts and a supersized pool. According to CNBC, its $218 million asking price makes it the most expensive home in Florida.

While that’s an outlier, even by Palm Beach standards, the U.S. is home to some extravagant exclusive islands where real estate prices are always at high tide. These U.S. islands have some of the most expensive homes.

Nantucket, Massachusetts

According to The Times, some of the most expensive real estate in the world is packed into the 14-mile by 3.5-mile stretch of land that is Nantucket, an isolated island off Cape Cod that is the southeasternmost town in Massachusetts and the New England region. 

The publication reported that President Biden had been vacationing there for 40 years and was a frequent guest of billionaire David Rubenstein at his $30 million-plus estate.

In the 1980s, homes were still available in the low six figures, but now the average price is $4.1 million. Prices in the famous summer playground of America’s elite soared by 40% between 2019 and 2024 as the monied class began to perceive the island as a safe haven in post-pandemic America. 

Recently, a seven-bedroom waterfront home sold for $24 million, but without an update since 1993, it was essentially a fixer-upper. In 2022, the owner of the Boston Red Sox sold his Nantucket home for $37 million. Small cottages and one-bedrooms have recently fetched millions, and rents can reach $85,000 a week.

Fisher Island, Florida

According to Mother Jones, Miami-adjacent Fisher Island is a 216-acre island with an official population of just 684 — but all 684 of those people are somebody. 

A perennial contender for the title of America’s wealthiest ZIP code, Fisher Island’s average resident declares $3 million in annual income, 10-figure wealth is the norm and famous inhabitants include or have included Oprah Winfrey, Julia Roberts, Mel Brooks, Andre Agassi, Boris Becker and Viktor Vekselberg, a sanctioned Russian oligarch who had three Fisher Island properties seized by the feds. 

The average condo sells for $9 million, but in 2023, a 10,200-square-foot, seven-bedroom property listed for $36 million. New residents have to part with a $350,000 initiation fee and ongoing costs of $23,005 per year to access the island’s world-class resort amenities.

The Real Deal recently reported that French perfume mogul Jean Madar is planning a half-dozen Fisher Island spec mansions ranging from $31 million to $55 million each.

San Juan Island, Washington

According to Realtor.com, the most expensive home in America is an 87-acre estate known as Halftide Farms on San Juan Island, just north of Seattle and south of Vancouver Island. Surrounded by 650 feet of private beach frontage, it consists of three separate luxury homes along with guest cottages, a caretaker’s home and amenities like tennis courts, two pools and four ponds.

It recently listed for $75 million, although the seller has since slashed the asking price to $58 million.

With a median sale price of $868,000, the island has options that don’t involve 11-figure, triple-mansion compounds. However, Redfin data shows the median sale price on the island is 99% higher than the national average and the cost of living is 80% higher, and Realtor.com reports that tech giants like Paul Allen and Bill Gates have homes there.

Maui, Hawaii

When you think of expensive island homes in the United States, Hawaii probably comes to mind before Massachusetts or Washington — and Maui is part of the reason. 

Maui is pricey even by the standards of tropical paradise, consistently ranking as one of the most expensive Hawaiian islands. According to Realtor.com, the median home on Maui lists for $1.2 million — but you can spend much, much more if you like.

Sotheby’s International Realty currently lists 119 properties for sale in Maui County, 19 of which are selling for less than $1 million. Nine cost $10 million or more — one is asking $18 million — with the other 91 falling between $1 million and $9.9 million.

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