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The 10 most expensive homes available on the North Fork right now

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Most of which are on Shelter Island


25 Nostrand Parkway, Shelter Island

At the number one spot, this seven-bedroom, seven-and a-half bath house is for sale in Shelter Island for $32,000,000. It’s been featured in Curbed Hamptons several times, mostly among the most expensive homes listings, appropriately. The 7,000-square-foot home was built in 1880. And though it’s the most expensive currently for sale on the North Fork, it’s still far behind the most expensive Hamptons home right now. Though a home on Gin Lane that’s listed as most expensive doesn’t show the price, the next highest one is for sale in East Hampton at $75,000,000, just to give some perspective.

Big E Farm, Jamesport

Quite a jump from $32 million, this home in Jamesport is listed at $20,000,000. For being over 10,000-square-feet, the home only has five bedrooms and six-and a-half bathrooms—but that’s because this is a farm, and the future owner will enjoy a whopping 200 acres of land. There are 17 buildings, including nine barns. The beautiful estate was built in 1994. The listing claims that there’s “room for tennis.” Very much agreed.

Oregon Road, Cutchogue

At $19,500,000, this home overlooks the Long Island Sound from Oregon Road. The structure itself is only 2,200-square-feet, with three beds and three baths. So why is it so expensive? Well, like the last home, this property sits on a huge piece of land—147.5-acres, to be exact. About 111 of those acres have development rights in tact, 26 of the acres are planted with varietal vines, and about 10 acres of the land has the home and pool that’s shown in the listing photos.

3 $ 4 Sylvester Road, Shelter Island

This $13,995,000 home was recently featured on Curbed Hamptons for its library and office. But the 8,000-square-foot home has a lot more to offer than just a killer library. The home, built in 1930, has eight bedrooms, eight baths, docking rights, screened-in porch, four-car garage, and a grand foyer. Emphasis on the grand. As with many homes built around this time, the home has maintained a classic architectural style, with renovations throughout to modernize appropriately.

27 Shore Road, Shelter Island

This Shelter Island home is going for $11,995,000. At 4,700-square-feet on 4 acres of land, this home includes seven bedrooms, eight baths, and panoramic views of the water in Dering Harbor. Particularly notable is the view of the water from the pool. Shore Road is certainly an appropriate name for the location. There’s both a main residence and a guest cottage, which is 1,200-square-feet and has four bedrooms. The kitchen has been renovated, and features designed appliances.

108 Ram Island Drive, Shelter Island

Though this home is tied with the previous listing at $11,995,000, this traditional style home seems to have a bit more of everything—or at least some things. The home is about 15,000-square-feet on a 4.3-acre lot, with 12 bedrooms and 14.5 bathrooms. It was built in 1929, and doesn’t have a pool or a guest cottage. But it does come with a dock, docking rights, and beach rights. Oh, and the dining room can seat 180.

7 Apple Orchard Lane, Shelter Island

Yet another Shelter Island estate tied for $11,995,000. One might recognize this home from being featured on Curbed Hamptons earlier this month for being one of the best waterfront rentals available on the North Fork. This Gambrel style home is 8,000-square-feet, with six bedrooms, seven-and a-half bathrooms, a heated pool, eat-in kitchen, exercise room, office, and outdoor shower. This property has a separate guest house, unlike the previous listing. It was built more recently as well, in 2007.

Dering Harbor, Shelter Island Heights

This list has officially dropped below the $10 million mark—this Shelter Island Heights home is for sale at $7,950,000. The 9,230-square-foot home has six bedrooms, six full baths, four half baths, a grand entrance foyer, a professional bar (seriously, there’s even a TV in there), wine cellar, movie theatre, and library. The home doesn’t have a pool, but according to the listing there are permits in place for one.

Undisclosed Address, Cutchogue

This 3,242-square-foot Cutchogue home is for sale at $7,500,000 with four bedrooms and two-and a-half bathrooms. But, similar to the last Cutchogue listing, this home sits on a very large property of 47 acres. Of that land, 32 acres is preserved farmland, and about five acres is part a vineyard. According to the listing, the Chardonnay and Riesling vines on the property are managed by a North Fork winery. The 1860s home is waterfront, with 460 feet of beach frontage.

4518 Sound Avenue, Riverhead

Tied with the previous listing at $7,500,000, this is the first Riverhead home on the list—making it the most expensive home in Riverhead on the market right now. And with 93 acres of land, there’s no wonder it’s priced where it is.