Historic New York Estate with Winery Listed by Former Weight Watchers CEO for $19.95M
June 13, 2025 – Former Weight Watchers CEO Mindy Grossman and her husband Neil Grossman have listed their expansive 60-acre Hudson Valley estate in Millbrook, New York, for $19.95 million.
The property blends American heritage with luxury living, featuring a main home dating back to the 1700s, a working winery, private trails, and over 13,000 square feet of living space. Originally purchased in 1998, the Grossmans lovingly preserved the home’s original stonework, beams, fireplaces, and flooring, while layering in eclectic, themed design touches throughout.
“We’ve never lost the heritage,” said Mindy Grossman. “It was always about honoring the integrity of the home.”
A Private Retreat with Curated Charm
Set half a mile from the road, the residence has a classic New England white façade with shuttered windows and rooms uniquely styled—from Victorian elegance to Parisian whimsy. Among the standout features is the Tartan House, a hidden two-bedroom wing decorated entirely in plaid—an homage to Grossman’s time at Ralph Lauren. It also includes a billiards room, bar, and home theater.
A Boutique Winery in the Heart of New York
Neil Grossman, a hedge fund founder, started Elysabeth Vineyards at Canoe Hill on-site in 2010. Producing 600 cases of wine per year, the vineyard is notable for being the only one in the Hudson Valley to successfully grow Cabernet Sauvignon and Merlot—grapes typically associated with Mediterranean climates.
“Climate changes made it surprisingly viable,” Neil explained. “It’s incredibly fulfilling to walk the land, feel the ripening grapes, and taste the Cabernet.”
The winery operation is fully on-site, including grape growing, bottling, a tasting room, and a prep kitchen for events.
Life, Family, and Legacy
The estate includes additional amenities such as a pool deck with a pizza oven, vegetable gardens, and serene walking trails. Mindy, a self-proclaimed walker and cook, cherishes the kitchen and family lounge area, where she and her daughter—after whom the vineyard is named—spend hours preparing meals together.
“It’s our huddle space,” she shared. “That’s where we connect.”
With their daughter and grandchildren now living in Florida, the Grossmans plan to relocate more permanently there while keeping a home in New York City.
Climate Migration Brings New Buyers to Hudson Valley
The estate originally hit the market in 2023 for $28 million, but was recently repriced to attract wider interest. According to listing agent Jason Karadus of Corcoran Country Living, the property is drawing buyers from places like Montecito and Santa Monica, as part of a growing trend he calls “climate migration.”
“We’re seeing high-end buyers seeking lifestyle and safety beyond traditional hubs,” Karadus noted.
With its unique blend of history, sustainability, and modern luxury, this Hudson Valley estate offers a one-of-a-kind living experience that’s as rooted in the past as it is future-ready.https://www.bizmartassets.com/tag/hudson-valley-real-estate/
