One of the oldest estates in Greenwich, tied to a well-known reality TV personality, has quietly changed hands in a private $7.8 million transaction.
Applejack Farm, a historic compound dating back to 1743, was recently sold by Real Housewives star Bethenny Frankel. The founder of Skinnygirl Cocktails originally purchased the estate in August 2021 for $4.25 million and made substantial upgrades to the three-acre property, which includes a five-bedroom main house, a two-bedroom guest cottage, a detached studio, and a renovated barn.
Frankel had already hinted at a relocation earlier this year. In April, she told followers on TikTok that she and her daughter, Bryn Hoppy, were moving to Florida for both personal and professional reasons. As it turns out, she had purchased a Miami Beach condo in June 2024 for $1.67 million, marking yet another addition to her evolving real estate portfolio, which has included a nearly $7 million loft in Manhattan and a luxurious estate in the Hamptons.
Jeff Jackson of Corcoran Centric Realty, who represented Frankel in the off-market deal, described the home as “a rare blend of historic pedigree and modern luxury nestled in the heart of the Golden Triangle of Greenwich.” That enclave, once regarded as the wealthiest neighborhood in the U.S. according to past analysis, is renowned for its grand homes and old-money prestige. Representing the buyer were Martha Z. Jeffrey and Anne Ogilvy of Sotheby’s International Realty’s Greenwich office.
Inside the main home, floral wallpaper decorates the foyer, where a classic arched entryway guides visitors into a wood-paneled living room anchored by a brick fireplace. Nearby, a sun-filled TV room boasts a white lacquered ceiling and walls of windows. The formal dining area features a gleaming wood floor bathed in natural light, while the updated chef’s kitchen showcases a La Cornue range, marble surfaces, and a built-in breakfast nook designed for bright morning meals.
The first floor also features a refined family room and a library, which stands out thanks to a green faux-crocodile ceiling and French doors opening onto a covered porch with views of the landscaped grounds. A pair of beverage bars are tucked throughout the house, including one in the lower level near a media room, gym space, and office. All five bedrooms are upstairs, including a primary suite with a fireplace and dual bathrooms that evoke spa-like luxury.
The grounds themselves offer just as much appeal. The new owner now holds manicured gardens, stone patios ideal for outdoor dining, and the aforementioned guest cottage with two beds and baths. The estate also includes a freestanding studio, a three-car garage, and a converted barn ready for entertaining.
