Shelter Island waterfront estate sells for $8.75 million

A waterfront estate on Shelter Island, overlooking Dering Harbor, sold Friday for $8.75 million in one of the most expensive sales on the tiny island in recent years.

The home, which was originally built as a carriage house in 1888, now includes more than 9,000 square feet of living space with six bedrooms, 10 bathrooms, and sun decks on the upper and lower floors. There are four interior fireplaces, a theater with tiered seating, an attached four-car garage, a bar and a wine cellar.

“There are these large separate spaces where family members can go and relax, but there are also a number of large common spaces where everyone could be together, and I think that was a huge factor in the appeal of the property to this particular buyer,” said Deborah Pirro, a real estate agent at Daniel Gale Sotheby’s International Realty in Westhampton Beach, who represented the seller.

Pirro declined to disclose the identity of the buyer and seller, who sold the home through a limited liability company. Angelo Piccozzi, an associate broker at Dering Harbor Real Estate on Shelter Island, represented the buyer. The home had originally been listed for about $9.5 million in late March.

The property, which spans 1.7 acres, includes 600 feet of private shoreline, a 166-foot deepwater dock and a heated saltwater gunite pool. Nearly all its rooms have water views of the harbor. It is located on the northern side of the island about a mile from the North Ferry to Greenport. The South Ferry to North Haven, near Sag Harbor, is a short drive away.

“You step off the ferry, and you're in another world,” Pirro said of the island, which is only accessible by ferry. “There are buyers that will avoid Shelter Island because of the ferry, but then you have people saying, ‘You know what, I’d rather take the ferry to Shelter Island than sit in traffic to East Hampton.’ ”

It was the fourth-most expensive sale on Shelter Island since 2021 among homes that were publicly listed, according to Judi Desiderio, CEO of Town & Country Real Estate, who tracks sales on the East End. The priciest deal on the island was a nearly $11.6 million sale in September 2021 for a compound with multiple dwellings, including a 10,000-square-foot house, on Coecles Harbor.

The sale this month was unusual for a luxury listing in that it didn’t stay on the market long, with Pirro showing the house to its eventual buyer within a week of listing, she said. The property, which underwent a major renovation in 2010, previously sold in 2007 for $3.5 million, according to Zillow.

There were 13 properties for sale on Shelter Island listed as of Tuesday, according to OneKey MLS. Prices ranged from about $625,000 for a three-bedroom Cape to $13.25 million for a 4-acre, two-lot property with a 6,000-square-foot farmhouse and permits to build an additional guest house.  

By Jonathan LaMantia

jonathan.lamantia@newsday.com@jonlamantia

Jonathan LaMantia covers residential real estate and other business news on Long Island. He previously covered the business of health care for Crain's New York Business.