Former Weight Watchers CEO Puts Historic Upstate New York Home up for Sale

Former Weight Watchers CEO Mindy Grossman, and her husband, Neil Grossman, are looking to sell their estate in New York’s Hudson Valley for $19.95 million. 

The 60-acre spread in Millbrook comes with a main home that dates to the 1700s, a functioning vineyard and tasting room, wooded acres, and over 13,000 square feet of living space.

The Grossmans bought the property in 1998 and have expanded and personalized it over the years. The five-bedroom main home is built around an 18th-century structure and the core of it still remains, including the flooring, stonework beams and fireplaces. 

“We kept the integrity of the original home,” Mindy Grossman said. “We’ve never ever lost the heritage.”

Set a half-mile back from the road, the classic New England-style features a white facade and shutter windows. Every room is curated with its own theme, from antique Victorian, to Paris-inspired to plush pinks and a library-slash-dining room with “ultimate dinner guest” decor.  

One area, hidden behind a painting that masks a doorway, is decorated entirely in plaid. Known as “Tartan House,” the space is a callback to Grossman’s time at Ralph Lauren, one of the various fashion companies where she worked in an executive role. It contains a full bar and billiards area, as well as two bedrooms and a theater. 

In 2010, Neil Grossman, who founded two hedge funds, embarked on a personal project of starting a winery, called Elysabeth Vineyards at Canoe Hill, which now grows seven kinds of grapes and produces 600 cases of wine a year. It’s unique because it’s the only Hudson Valley winery to produce a Cabernet Sauvignon or Merlot, which are traditionally grown in more Mediterranean climates. That’s likely due to the changing climate, Neil Grossman said. 

“I felt that there was a really reasonable chance that the temperature would be a little bit more conducive to those grapes, and it turned out to be that way,” he said. “There’s no doubt that the ability to ripen these grapes has been surprisingly good.”

The winery is in-house from start to finish, from growing the grapes to packaging the boxes. It also includes a tasting room, an entertainment pavilion, and another residence with a prep kitchen, so it’s all set up for entertaining, Neil Grossman said. 

The winery, and the property in general, are very different from where Neil Grossman grew up, so he appreciates nature and the privacy it offers. 

“I grew up in the Bronx. I grew up on concrete,” he said. “To wander across our property during the summer time, feel the grapes as they’re ripening, taste the cabernet sauvignon…It’s just that sort of enveloping property.”

Other parts of the property include a pool deck with an outdoor kitchen and pizza oven, several ponds where Neil likes to golf, vegetable gardens the family picks for cooking, and a walking trail that Mindy Grossman likes to use. “I love to walk,” she said. “That’s my release.”

In general, her favorite parts of the home are the ones that bring family and community together, particularly the kitchen area where she and her daughter, whom the winery is named after, love to cook and the adjacent family area. “That’s our huddle space,” she said. “We’re big cooks.”

The Grossmans plan to spend more time in Florida, where their daughter and grandchildren live, and still have a home in New York City. 

The property initially came to market in 2023 for $28 million, and the new price is designed to bring more interest, said listing agent Jason Karadus of Corcoran Country Living, who will be listing the property in the coming week. These days, he’s seeing buyers from further afield, such as the Hamptons or California, who may be moving due to climate concerns. 

“We are seeing an incredible uptick and what I call climate migration,” he said. “The last couple deals we’ve done over $10 million that we’ll be closing this month were people moving from California, one from Montecito and one from Santa Monica.”

At least they’ll find some familiar grapes so far from home.

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