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The Priciest Home in Shelter Island Chops Off $7 Million

The waterfront estate is now asking $25M

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Jake Rajs
Jake Rajs

The most expensive home ever on the market in Shelter Island, New York, has cut its asking price to $25 million, a $7 million or 22% deduction from when it first came on the market last July.

Despite the large discount offered Tuesday, the 7,000-square-foot waterfront estate on Nostrand Parkway is still twice as expensive as the next priciest property on Shelter Island, a $12.5-million 8,000-square-foot residence on Sylvester Road, according to Realtor.com, which, like Mansion Global, is a subsidiary of News Corp.

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The highest priced single-family sale ever on the island is a 5,100-square-foot home, which changed hands for $9.5 million in 2014, according to the Shelter Island assessor’s office.

Shelter Island is an 8,000-acre island on the tip of Long Island which can only be reached by ferry or private plane.

For its current price tag of $25 million, the estate offers 4.8 acres, more than 400 feet of water frontage and a Queen Anne Victorian-style home built around 1890 and renovated in 2007. The three-story main residence has seven bedrooms, seven full bathrooms and one half bathroom, a living room with two fireplaces and multiple sitting and dining areas, according to the listing with Sotheby’s International Realty.

Adjacent to the main residence is an iconic windmill guest house with an entertainment level, a fully-equipped guest suite, as well as a stairwell leading to the top of the spire with ocean views.

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At the entrance,  a century-old maple tree and a flag pole that was the mast of a vessel Sir Thomas Lipton raced in the 1930s America's Cup, speak to the history of the home. Amenities on the grounds, though, are all about modern conveniences and comfort. Those extras include an 80-foot L-shaped dock, a boat house, a pool, a tennis court and a basketball court.  Listing agent Beate Moore of Sotheby’s didn’t immediately respond to a request for comment.

The owner, Dick Tarlow, a retired advertising executive known for marketing products for Revlon and Ralph Lauren, bought the home in 1983 with his then-wife for $640,000. He couldn’t be immediately reached for comment, but had told The Wall Street Journal when he put the home on the market in 2016 that he planned to split the proceeds from the sale among his three children.

Curbed first reported the price cut.