Waterfront Compound On Nantucket Harbor Sells For $24 Million

Jason Graziadei •

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A nearly century-old waterfront compound on Nantucket Harbor sold Friday for $24 million, placing it among the most expensive real estate transactions in island history.

The property at 42 Shimmo Pond Road, known as "Low Shimmo," was originally built in 1928 and has been owned by the family of the late businessman and naturalist James Stewart since 1988.

On Friday, the trust controlled by Stewart's children sold the 1.58-acre property to ACK Koda LLC, a limited liability company managed by Anastasios Parafestas, of Boston. The owner of record was not listed.

The seven-bedroom, seven-and-a-half bathroom estate was renovated in 1993 by architect D. Neil Parent, and includes a 400-foot private dock, the largest on the island.

Great Point Properties' Greg McKechnie and attorney Sarah Alger represented the family trust that sold the property, while Lee Real Estate's Carolyn Durand and attorney Steven Cohen represented the buyers.

"The buyer intends to update the interior and make other improvements through the ordinary HDC (Historic District Commission) and ConCom (Conservation Commission) permitting process, both of which are very limiting here," Cohen said.

The property had been listed by Great Point Properties and was on the market for $28 million up until Friday's closing. 

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42 Shimmo Pond Road

The $24 million sale is among the highest ever recorded on Nantucket, yet still well below 2023's record-breaking $44 million sale of 72 and 68 Monomoy Road to Barstool Sports founder Dave Portnoy.

It's also located close to another property that briefly held the all-time island sales record: Red Sox owner John Henry's estate at 4 Middle Valley Road and 48 Shimmo Pond Road which were purchased in separate transactions totaling $37 million in 2022.

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