Fashion entrepreneur Kenneth Cole is once again testing the luxury real estate market, relisting his longtime Westchester County estate for $16 million after temporarily pulling it from sale while actor George Clooney rented the property during his acclaimed Broadway run in Good Night, and Good Luck.
The listing marks another chapter in the remarkable history of one of Purchase, New York’s most distinguished private estates—a property Cole has owned since 1991, when he acquired it for approximately $2.8 million. For more than three decades, the sprawling compound served as the primary family residence for the designer, whose eponymous fashion brand became one of the most recognizable names in American retail.
Located about an hour north of Midtown Manhattan in the affluent hamlet of Purchase, the estate combines the privacy of a country retreat with convenient access to New York City, making it particularly attractive to high-profile executives, entertainers, and business leaders seeking a discreet primary or secondary residence.
From Family Estate to Hollywood Rental
Cole first brought the property to market in 2024 with a $22 million asking price, explaining in interviews that the timing felt right after his children had grown and moved on.
However, plans to sell were temporarily put on hold when George Clooney leased the estate while starring in the Broadway adaptation of Good Night, and Good Luck. The Oscar-winning actor reportedly sought a private retreat within commuting distance of Manhattan, making the Purchase estate an ideal fit.
Now back on the market at a revised $16 million asking price, the property presents a rare opportunity to acquire a celebrity-owned estate with both architectural pedigree and cultural significance.
A Private Country Manor on More Than 11 Acres
Hidden behind gates at the end of a winding driveway, the estate spans approximately 11.35 acres of meticulously maintained grounds.
The property is marketed as an exceptionally private country manor, surrounded by rolling lawns, mature specimen trees, and gardens cultivated over more than three decades. Seasonal plantings ensure year-round color, while carefully planned landscaping creates a sense of serenity rarely found so close to New York City.
Among the outdoor amenities are:
- A fenced saltwater swimming pool and terrace
- A multi-hole practice golf green
- A meditation garden
- A one-acre freshwater pond stocked with koi and carp
- Multiple outdoor entertaining areas
- Extensive walking paths and landscaped lawns
The setting evokes the atmosphere of a luxury country estate rather than a typical suburban residence.
Nearly 12,000 Square Feet of Refined Living Space
The three-story residence encompasses approximately 11,792 square feet and contains seven bedrooms, multiple entertaining spaces, and expansive garden views from nearly every room.
Visitors enter through a grand foyer highlighted by an elegant curved staircase that establishes the home’s classic aesthetic. Formal and informal living areas feature fireplaces, oversized windows, and detailed millwork that create a balance between sophistication and comfort.
One of the home’s standout spaces is its impressive formal dining room, which can reportedly accommodate up to 80 guests, making it ideal for large-scale entertaining, charitable events, and family celebrations.
The residence also includes dual living rooms, one opening directly onto a covered veranda overlooking the grounds.
A Chef’s Kitchen Designed for Entertaining
The heart of the home is an extraordinary chef’s kitchen anchored by a custom hammered copper-and-wood island.
Luxury features include:
- Two La Cornue ranges
- Premium professional-grade appliances
- Custom cabinetry
- Sunlit breakfast area
- Adjacent family room
- Direct patio access
The kitchen was clearly designed to support both everyday family living and large-scale entertaining.
A Luxurious Primary Suite
Occupying a privileged position within the residence, the primary suite offers a level of privacy typically found in boutique luxury hotels.
Features include:
- Two private balconies
- Dual walk-in closets
- Two spa-like ensuite bathrooms
- Fireplace
- Garden views
The primary bath showcases elegant wood detailing, marble vanities, and a freestanding soaking tub designed as a centerpiece of the space.
Space for Car Collectors and Guests
The estate also appeals to automotive enthusiasts, offering multiple garage structures including:
- Attached two-car garage
- Dedicated golf cart garage
- Detached four-car garage
- Additional covered parking
Combined, the facilities provide ample room for vehicle collections, guest parking, and recreational equipment.
A Home With Hollywood History
Long before George Clooney became a temporary resident, the property had already earned a place in cinematic history.
The estate served as a filming location for the 1969 romantic comedy-drama Goodbye, Columbus, adding another layer of cultural significance to an already notable residence.
Its combination of privacy, architectural character, and proximity to New York City has made it attractive to filmmakers and high-profile residents for decades.
Kenneth Cole’s Legacy Beyond Fashion
The home reflects the success story of Kenneth Cole himself. After founding Kenneth Cole Productions in 1982, the designer transformed the company into a global fashion brand. The business went public in 1994 and eventually achieved a valuation approaching $1 billion before Cole took it private in 2012 to pursue a more entrepreneurial vision.
Today, as Cole prepares to part with a property that has been part of his life for more than thirty years, the estate stands as both a personal legacy and a unique offering within the New York luxury housing market.
A Rare Opportunity in Westchester County
Luxury inventory of this scale and quality remains relatively scarce in Westchester County, particularly within the Purchase market, where large parcels, privacy, and proximity to Manhattan continue to command strong demand among affluent buyers.
With celebrity provenance, a history that spans fashion, film, and Broadway, and more than 11 acres of curated grounds, Kenneth Cole’s former family estate represents far more than a luxury home—it is a legacy property that blends country living, architectural elegance, and cultural significance in one of New York’s most sought-after enclaves.