There Once Was a House in Nantucket: Massachusetts’ Most Expensive

A captivating compound that was a former beach club on Nantucket now holds the title of the most expensive listing in Massachusetts.

On the market for $39 million, the 1-acre waterfront property was originally a private beach club in the 1930s. Today, it’s a “versatile property” anchored by a four-unit beach house and two cottages.

“One of the free-standing beach cottages has been kept [in] its original 1930s style,” says listing agent Allison Mazer, of Compass. The property also comes with two garages, a lovely courtyard, and a large parking area.

The compound’s location on Cliff Beach feels “very secluded” even though it’s less than a mile from town, adds Mazer. It sits next to the Cliffside Beach Club, a luxury hotel.

Aerial view


Open floor plan


Oceanfront view




Dining area




All told, the current configuration offers 10 bedrooms, 10 bathrooms, and over 7,200 square feet of living space.

The versatile property, which has become a Nantucket landmark, was built to last. Many waterfront properties on Nantucket have either erosion or flood issues—or both, says Mazer. But this property doesn’t have those concerns “due to protections afforded by the west jetty and [the property’s] high elevation.”

For an entrepreneurial buyer with development experience looking to cash in on the island’s bustling tourism, this pricey property could prove tempting. It’s the only property on the island’s north shore that’s zoned for residential and commercial use.

“It’s a great portfolio for a hotel, extended stay, or residential compound,” says Mazer. “It would also be a great opportunity for a boutique hotel.”

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