New Cliff Road Mansion Hits The Market At $45 Million

A Nantucket property on Cliff Road hit the market last week with an astounding asking price of $45 million.

The recently completed estate at 33 Cliff Road features a main residence, a guest house that can be accessed through an underground tunnel, a swimming pool, a two-car garage with a studio, gym, movie theater, and billiard room. 

If sold at its asking price, the Cliff Road compound would set a new Massachusetts record for a residential property. Nantucket had held the record for several years following Barstool Sports founder Dave Portnoy's $42 million purchase of a compound in Monomoy in 2023. But Martha's Vineyard just claimed the distinction with a $43 million sale in September 2026.

The Cliff Road compound was built by Hehir Group Custom Builders and designed by Botticelli & Pohl Architects. According to property records, it was most recently sold in September 2024 for $13.9 million to 33 Cliff Road LLC.

According to its listing with Great Point Properties, the property is being sold fully furnished and "features a spectacular main residence and substantial guest house with nine bedrooms in total, complemented by a swimming pool, two-car garage with studio, gym, movie theatre, billiard room, and expansive outdoor living and entertaining spaces. A private tunnel connects the main residence to the guest house, while a widow’s walk provides an elevated vantage point for taking in sweeping views across the Cliff landscape and Nantucket Sound."