Real Estate Top 5: North Fork Fabulous

Harvest season on the East End is almost upon us, a time when locals and second-home owners alike immerse themselves in all the area has to offer. Vineyards, beaches, bucolic surroundings—no rhapsodizing about the beauty of the North Fork would be complete without a celebration of the outstanding properties that are part of its bounty, highlighted by this quintet that soar from the superlative to the sublime.

Wine Country Wonderland   Jamesport/Riverhead  $25,000,000
Wine Country Wonderland

Big E Farm and Martha Clara Vineyards from Sheri Winter Clarry

If you’ve always wanted your own home on the range but also wanted to stay within close range of the ocean and New York City, this spread in Long Island Wine Country is your answer. Named Big E Farm after current owner Robert Entenmann, an heir to the Entenmann’s bakery fortune, the property (pictured above) includes its own horse farm as well as the famed Martha Clara Vineyard.  At over 204 acres, this is the largest single parcel currently for sale not just on the North Fork but on all of Long Island. More than 113 of those acres are currently “under vine,” planted in the beautiful rows of wine grapes that give the North Fork its pastoral charm. The grounds are dotted with numerous picturesque barns and other buildings related to the vineyard and horse farm, and Big E Farm’s mansion house, with more than 10,200 square feet of space, boasts 5 bedrooms, 6.5 baths, a heated pool, formal dining room and every imaginable amenity, including a commercial-grade bakery in the main house. Well, it is Entenmann, after all.

Water, Water Everywhere

Location, location, location—that’s one for each of the three waterside decks you could find youself lounging upon at this custom home that takes impeccable advantage of its vistas at every turn. Views of the Long Island Sound and glorious sunsets are to be relished from any of those aforementioned decks, or poolside while sipping a drink prepared at the outdoor bar, or even while strolling along the rolling lawn resting between the house and the horizon. Inside, gorgeous windows and doors offer 180-degree panoramic water views throughout. A personal elevator will take you up to a master bedroom on both the first and second floors, then down to the basement complete with game room. And since this is Long Island Wine Country, after all, the wine room is the perfect perk form making the most of those local vintages.

Love This Landmark


If you’ve ever driven out to Orient Point to catch the ferry or meander around the state park, then you’ve seen the Cedars.  This 1883 landmark sits elevated on 4.8 acres overlooking Long Island Sound and Orient Harbor, presenting its magnificence to visitors coming across the Route 25 causeway from points west. Now after more than 130 years of ownership by the same prominent Brooklyn family that built it, the Cedars is being offered on the open market for the first time. In addition to getting a little piece of local history, the new owner will enjoy a beautifully preserved Victorian mansion with a massive wraparound stone porch, 6 bedrooms, an attached guest house and an in-ground pool, plus 450 feet of private Long Island Sound frontage. With unparalleled vistas of the famed Bug Light lighthouse and Shelter Island, the Cedars provides the perfect orientation for viewing picture-perfect North Fork scenery.

Bay Front Beauty<br>Cutchogue<br>$14,600,000
Bay Front Beauty
5250 Vanston Rd, Cutchogue
Courtesy Daniel Gale/Sotheby’s More info

There’s Cutchogue bay front and then there’s Nassau Point bay front. This estate offers 15-plus pristine acres on Nassau Point, a narrow strip of paradise that extends out into Peconic Bay. In addition to more than 1,000 feet of beach frontage and a boat basin on the bay, the property includes two waterfront lots on exclusive Wunneweta Pond. The 8-bedroom mansion dates to the 1920s and still reflects the simpler aesthetics of its day. There’s an additional guest cottage, boathouse and clay tennis court, but what’s truly unusual here is how much of the property’s acreage appears to be untouched: it remains wooded and park-like, ready for careful, sensitive evolution into a new owner’s personal North Fork dreamland.

Family Time Living<br>Cutchogue<br>$4,750,000<br>
Family Time Living
8871 Oregon Road, Cutchogue
More info

The Hamptons and the North Fork have distinct personalities and feels, but this single-family home in Cutchogue mixes the North Fork location with a Hamptons style. With 22 acres of land, there’s a lot of potential for all kinds of development—maybe you want to start a vineyard or some other kind of creative endeavor that’s unique to the North Fork. This custom-built cedar home has 7 bedrooms, 5 full bathrooms, a finished, full basement, dining room, eat-in kitchen, family room and office space. It’s ready to entertain, too, with a tennis court and in-ground heated infinity pool. And it’s right on the Long Island Sound, so you can look out and watch the sea from the comfort of your home.

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