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New York's Shelter Island: Not Quite The Hamptons and Loving It

This summer, our brethren over at Curbed Hamptons conducted several surveys to determine just where regular, ol' Long Island ends and "The Hamptons" begins. Even with all the numbers tallied, there's still plenty of disagreement along the South Fork, but one maxim saw no contention: Shelter Island is not part of the Hamptons. Accessible by ferry from both the North and South Forks, the island maintains a culture and appearance distinct from either. That's not to say that their aren't some Hamptons-esque mansions on this independent island, as it's been a wealthy getaway since the turn of the century. This $3.5M Tudor-style estate has quite the tony history. The six-bedroom waterfront home was allegedly built for President McKinley, who was assassinated before he could enjoy it, and later hosted baseball legend Babe Ruth and Peter Pan creator J.M. Barrie. Primrose, as the house is known, is a little short on listing photos, but is said to retain many of the original features, like an Art Nouveau sun room, moldings, oak floors, walnut wainscoting, and six unique tiled fireplaces.

? This sprawling stone-and-stucco manor, completed in 2007 to cap a 5.6-acre property in the "heart of the Village," is being a bit shy about its asking price, but it has recently fetched a seasonal monthly rent of $45K, so it's surely a multimillion-dollar property. That's none too surprising, considering the 7,000 square feet, six bedrooms, 1,000-bottle wine cellar, swimming pool, and a 1940s Lord & Burnham greenhouse.

? With roughly half the land and half the square footage of the last place, Little Ram isn't nearly as tight-lipped about the asking price: $6.8M. Before you get to thinking that means the previous one is an eight-figure mansion, keep in mind that Little Ram's three acres are waterfront and include a dock and mooring. Plus, the architects managed to squeeze seven bedrooms into the 3,800-square-foot spread when the place was built back in 2005.

? Let's get back to the history with the Griffing House, built in 1911. Built by the operator of the island's North Ferry Company, this house is set on six acres of lawn and woods and, despite a couple of misguided renovations, retains much of the original detail. The massive old barn has been converted into an expansive entertaining space—with upstairs bar, kitschy details, and rustic kitchen—but could also be used as a guest house. The Griffing House is asking $2.45M.

? For simpler country living at a much lower price, this petite waterfront cottage could be just the ticket at $650K. Built in the 1930s, the four-bedroom house measures just 1,400 square feet, but sits on a spacious 1.1-acre lot with sunset views over the water. As an added bonus, there's a detached two-car garage.

· It's Official: The Hamptons Begins At The Shinnecock Canal [Curbed National]
· Historic Waterfront Tudor Manor [M. Wein Realty]
· Oriole Farm - Dering Harbor [M. Wein Realty]
· Oriole Farm - Rental [M. Wein Realty]
· Little Ram [M. Wein Realty]
· Griffing House [M. Wein Realty]
· Bungalow [M. Wein Realty]