Top 5 Most Expensive Homes on the Market in the Hamptons

Size matters when it comes to property…or at least a property’s price tag. The higher the cost of a home, the more buzz it seems to generate. It’s not just the dollar signs that inspire interest, but the little extras that those dollars dictate. It could be a football field’s worth of waterfront or a rich history or a Richard Gere. Whatever strikes your fancy, at least one of the five most expensive Hamptons homes on the market must have it.

  • Wooldon Manor.

    Wooldon Manor, Southampton, $98,000,000.
    Photo credit: Chris Foster

    This classic Gin Lane oceanfront estate comes with a history. Built in the 1920s for the Woolworth family (whence the name “Wooldon Manor”), and later owned by Merrill Lynch founding partner Edmund C. Lynch, this Tudor-style mansion boasts 10 bedrooms and 12 full bathrooms. Period details include limestone floors and custom bronze doors, and most of the bedrooms give direct access to exterior terraces and lawns. The grounds feature formal gardens, a magnificent pool and pool house, a picturesque greenhouse, and a tennis court. At 12,800 square feet, Wooldon Manor is not enormous by contemporary standards, but what makes this listing so enviable is not just the house but the land it’s on—15 oceanfront acres in Southampton don’t come along very often. And it’s not just the 15 acres, but the potential they offer. Aside from the 5.25-acre lot that the mansion is on, the remaining acres are subdivided into four buildable lots. One can imagine the possibilities for the right buyer: keep the land undeveloped as a private park, start a family compound…or let the next owner figure it all out. There’s a recent history of that sort—this property was just purchased only last December for $75,000,000.

  • Villa Maria

    Villa Maria, Water Mill. Photo credit: Cully/EEFAS

    Villa Maria is among the more visible estates in the Hamptons, with its wrought iron gates and white stucco walls standing right next to Montauk Highway as it rounds the bend heading into Water Mill. An estate like this one would require an owner who didn’t mind the visibility of such a location, and also might favor a buyer with a taste for history.

    Villa Maria’s past is even more involved than that of Wooldon Manor. The property was originally developed in the late 1800s by a group of businessmen who took the unusual step of moving the Corwith Windmill to sit on their front lawn, in the place where it stands to this day. (The windmill and the land on which it sits are no longer part of the estate, but were sold to the village some time ago.) The mansion itself took on its current shape starting in 1919, when a new owner hired prominent architect Frank Freeman to essentially rebuild the entire property. At that time, the property acquired the nickname “Red Gables,” due to the addition of a red-tile roof.

    Fast-forward to the 1930s, when the Great Depression made estates like Red Gables impossible for many to sustain. The Roman Catholic Church stepped in to buy the property, eventually turning it into a school for aspirants to sisterhood. It was at this time that the estate took on the name “Villa Maria.” Villa Maria was purchased from the church in 2005, and has since been both restored and modernized. With 22,000 square feet of floor space, the mansion houses 11 bedrooms, with a super-luxurious 6-room master suite. Designed to take advantage of its unique location right on Mecox Bay, all of the principal rooms in the mansion—including the 60-foot living room—feature panoramic water views. The house sits on 11 acres with a dock, a waterside pool and cabana, tennis court, and two-story portico. In addition to the main house, the estate also boasts a separate two-room guest cottage.

  • Georgica Pond Compound, East Hampton, $67,500,000.

    Georgica Pond Compound, East Hampton, $67,500,000. Photo credit: Courtesy Sotheby's

    Georgica Pond is more about prestige and privacy than any sort of “hey-look-at-me” prominence. Towering mansions with gilded pedigrees are not really the allure of owning a premium property on Georgica Pond, where instead owners get the quieter glory of location, location, location.

    This impressive offering only confirms that notion, affording the opportunity to create a 6-acre empire in arguably the most exclusive neighborhood in the Hamptons. The property is divided into four separate lots, two of which have preexisting structures: a 7,500 square-foot main house with a pond-side pool on one and a three-bedroom guesthouse on another. The remaining lots, which may also be sold separately, are the stuff upon which dreams, and perhaps dream houses, may be built.

    But let’s face it—this isn’t just about houses.

    This is about two words: Georgica Pond.

    The combined acreage for sale here sports an enviable 481 feet of frontage directly on the legendary East Hampton pond. Does Steven Spielberg have that much?

  • Bayfront Mansion in Mecox Water Mill. On the market for $58,500,000

    Bayfront Mansion in Mecox, Water Mill, $58,500,000

    Water Mill is the center of it all. Situated close enough to East Hampton for a day trip or a night out for dinner, but not so close that you’re going to have to fight traffic on Montauk Highway for hours just to get to your new 20,000 square-foot, 8-bedroom, 10-and-a-half-bath Hamptons pad on the bay.

    Mecox Bay has long been one of the most underrated bodies of water on the East End. When was the last time you drove by and spotted someone on the water? Would that be…never? Correct. This house is perfect for the kayaking, sailing or trendy stand-up paddleboard enthusiast. Come the winter, watch the iceboats—with eight fireplaces, heat won’t likely be a problem.

    You’ve got the property. Now what about the amenities? The history and architecture buff will revel in the 19th Century mantels, coffered ceiling and more than 120 exterior architectural brackets. The grand entrance opens to a cast bronze double staircase and a 19th Century stained-glass skylight. As for creature comforts, enjoy the infinity edge pool, Jacuzzi, tennis court, wine cellar, gym, theater, sauna, dock and koi pond (after all, what are creature comforts without a few creatures?). When you’re not at one of the fab Hamptons restaurants, prepare a world-class meal in a kitchen designed by Mark Stech-Novak, with a separate prep-kitchen, bakery and main kitchen, including a custom-made Molteni range stove.

    Sounds like the kind of place you’d never want to leave. But if you had to, you wouldn’t have to feel homesick—the entire estate can be controlled and monitored from anywhere in the world through a Creston security camera and entertainment system.

  • Strongheart Manor, North Haven, $56,000,000

    Strongheart Manor, North Haven, $56,000,000.
    Photo credit: sothebys.com

    Owner Richard Gere no doubt adds an air of celebrity to this property, but a thespian vibe inhabited the soul of Strongheart long before the Pretty Woman star showed up. Legend has it that the name came from a character that actor Robert Edeson played on Broadway. Of course, the manor sports plenty of star power on its own as it celebrates its 112th birthday.

    Amid the private 6.3 tranquil acres tucked away from the heart of Hamptons hubbub, the same neighborhood Jimmy Buffett calls home, there are views of Peconic Bay and Mashomack Preserve on Shelter Island, 300-plus feet of waterfront and dock permits, an outdoor fireplace pavilion, a half-court basketball court, and a teahouse set in the middle of a pond. The Strongheart Manor house anchors the estate, with two additional guest houses on three single and separate lots, and 12 seems to be the magic number here—12 full bedrooms, 12 full baths, 12,000 square feet. Endless possibilities.

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