Drew Barrymore Lists 280-Year-Old Westchester Estate for $5 Million—Just 2 Years After Buying It

Actress-turned-talk show host Drew Barrymore is parting ways with her historical Westchester retreat after putting the sprawling abode on the market for $4.99 million—just two years after she bought it.

Barrymore, 51, snapped up the six-bedroom, nine-bathroom property for $4.4 million in 2024, according to property records. She then spent more than a year pouring even more money into an extensive renovation of the abode, which she admits to the Wall Street Journal was in much rougher shape than she had initially anticipated.

What began as a cosmetic overhaul soon turned into a “complete internal gut,” during which the actress had to replace a majority of the key systems in the home, which was originally built in the 1740s. They included the heating, the plumbing, and the air conditioning.

The main level of the home also received a drastic transformation, thanks in large part to Barrymore’s desire to open up the kitchen and fill it with light, a feat that she confessed “took a year of engineering to figure out.”

While she didn’t share specific details about the cost of the work, Barrymore joked that her experience was much like that of “The Money Pit” character Anna, played by Shelley Long, who—along with her husband, Walter—ends up purchasing a home that they quickly realize is close to falling apart.

Drew Barrymore Lists 280-Year-Old Westchester Estate for $5 Million—Just 2 Years After Buying It
Actress-turned-talk show host Drew Barrymore is parting ways with her historical Westchester retreat after putting the sprawling abode on the market for $4.99 million—just two years after she bought it. (Modern Angles )
Drew Barrymore Lists 280-Year-Old Westchester Estate for $5 Million—Just 2 Years After Buying It
Barrymore, 51, snapped up the six-bedroom, nine-bathroom property for $4.4 million in 2024, according to property records. (Modern Angles )
Drew Barrymore Lists 280-Year-Old Westchester Estate for $5 Million—Just 2 Years After Buying It
She then spent more than a year on an extensive renovation of the abode. (Modern Angles )
Drew Barrymore Lists 280-Year-Old Westchester Estate for $5 Million—Just 2 Years After Buying It
What began as a cosmetic overhaul turned into a “complete internal gut” of the home, which was originally built in the 1740s. (Modern Angles )
Drew Barrymore Lists 280-Year-Old Westchester Estate for $5 Million—Just 2 Years After Buying It
Barrymore, who has a strong passion for home design, did much of the interior decor herself. (Modern Angles )

However, Barrymore came through the renovation relatively unscathed, transforming the property into a true sanctuary that she believed would serve as her family’s escape from the city, where she shoots her popular talk show.

Indeed, she said she initially purchased the 12-acre estate because it was located in a much more convenient and easily-accessible location than the Hamptons, where she had previously owned a home, but found herself too busy to really visit thanks to her kids’ increasingly hectic schedules.

But Harrison, NY, where her Westchester home is located, offered a much easier retreat for the star—accessible within an hour by car, whereas Sagaponack, where her Hamptons property was located, can take closer to three hours to reach.

Having invested so much time, energy, and money in renovating the dwelling, many might wonder why Barrymore is choosing to sell, less than a year after that work was finally completed.

The answer, she noted, is simple: Because the overhaul took much longer than she had anticipated, she could not have foreseen how the needs of her family would change during that time, leaving her without a real need for the countryside sanctuary.

That being said, the project did give the on-screen star an opportunity to indulge in one of her greatest personal passions—interior design, something that she has long said is one of her favorite creative outlets.

While many A-list stars might leave the work to the professionals, preferring instead to oversee the progress from the comfort of their fully renovated primary residence, Barrymore did the exact opposite, even living at the property when it was in the most basic of states.

Drew Barrymore Lists 280-Year-Old Westchester Estate for $5 Million—Just 2 Years After Buying It
She noted in a new interview that she filled the home with much of the furniture that she had used in her California dwelling. (Modern Angles )
Drew Barrymore Lists 280-Year-Old Westchester Estate for $5 Million—Just 2 Years After Buying It
One of the most labor-intensive parts of the renovation was opening up the kitchen to make it feel more spacious. (Modern Angles )
Drew Barrymore Lists 280-Year-Old Westchester Estate for $5 Million—Just 2 Years After Buying It
She noted that one of the key reasons she purchased the home was her desire to spend more time in nature. (Modern Angles)
Drew Barrymore Lists 280-Year-Old Westchester Estate for $5 Million—Just 2 Years After Buying It
Having invested so much time and money in the renovation of the property, Barrymore said that she had chosen to sell it because her family’s circumstances had changed in the time it took to complete that work. (Modern Angles)
Drew Barrymore Lists 280-Year-Old Westchester Estate for $5 Million—Just 2 Years After Buying It
The listing for her Westchester dwelling describes it as “a rare legacy estate where every room has been thoughtfully reimagined for the perfect moment.” (Modern Angles)

“I lived in the house in the most primitive of scenarios,” she revealed. “It’s some of my favorite times and memories.”

And when it came to the design choices in the property, Barrymore led the charge, selecting a majority of the furniture, finishes, and even the paint colors, which can be seen in the listing photos.

Before putting the property on the market—where it is listed with Kori Sassower and Brian K. Lewis of Compass—Barrymore seized the opportunity to make at least one more core memory there, when she celebrated her 51st birthday with some of her closest friends.

Despite the bitter February weather, the “Charlie’s Angels” star admitted that she couldn’t resist the chance to enjoy the stunning landscape that surrounds the property—or the opportunity to relive her earliest days living at the home when it had no real amenities, or even a real kitchen.

So, they braved the freezing temperatures and, while wearing “parkas, hoodies, gloves, and face masks,” spent the evening grilling.

The great outdoors is what originally drew Barrymore to the house, she revealed earlier this month, when she explained to Rue Magazine that she had wanted to find a dwelling that would allow her to connect with nature—and her California roots.

“I had desperately wanted a place outside the city because I had been working for years at this point inside of a studio with no windows,” she said. “I’m from California, and I just had this urge to find nature.”

After finding a listing for the Westchester house online, the actress said she was immediately drawn to the home in a “spiritual” way.

“I came here and I walked around and I was like, I swear my family has been in this house,” she said. “I don’t think I’m super woo-woo, but I had this really strong sense and feeling.”

Drew Barrymore Lists 280-Year-Old Westchester Estate for $5 Million—Just 2 Years After Buying It
There are a total of six bedrooms spread across the main residence and the guesthouse. (Modern Angles)
Drew Barrymore Lists 280-Year-Old Westchester Estate for $5 Million—Just 2 Years After Buying It
The primary suite comes with two bathrooms, as well as an expansive walk-in closet. (Modern Angles)
Drew Barrymore Lists 280-Year-Old Westchester Estate for $5 Million—Just 2 Years After Buying It
There is also a beautiful conservatory, which offers stunning views of the 12-acre property. (Modern Angles)
Drew Barrymore Lists 280-Year-Old Westchester Estate for $5 Million—Just 2 Years After Buying It
The detached guesthouse offers a loft, living room, full bath, and kitchen. (Modern Angles)
Drew Barrymore Lists 280-Year-Old Westchester Estate for $5 Million—Just 2 Years After Buying It
The grounds are home to a gunite swimming pool and a wildflower garden. (Modern Angles)

Barrymore has not revealed whether she has found herself another fixer-upper to tackle—or if she has decided to take a break from DIY projects and focus on life at her New York City apartment, which serves as her primary residence.

However, the listing for her Westchester dwelling makes no secret of the vast amount of work that was put into the property, describing it as “a rare legacy estate where every room has been thoughtfully reimagined for the perfect moment.”

For those seeking their own weekend retreat, the property—which spans more than 7,200 square feet—offers ample room to relax in the beauty of the natural landscape, boasting a sizable main house, a finished pool house, and a separate guest cottage

Inside the primary structure, visitors will find bright open spaces, elegant design details, and many communal living areas, ideal for those with a fondness for entertaining.

“The floor plan offers exceptional flexibility as the open spaces flow between the kitchen, dining room, sitting room, sunlit conservatory, cozy family room, expansive living room, and additional gracious entertaining spaces, all of which are enhanced by the multiple fireplaces, creating a sense of warmth, comfort and connection throughout,” the listing says.

Among its more impressive features are an extraordinary great room with a 30-foot ceiling, as well as an expansive primary suite that boasts a sitting room, balcony, enormous walk-in closet, and two bathrooms.

While much of the grounds surrounding the home are filled with trees—creating a true sense of solitude and privacy—there is also plenty of room for entertaining, whether on the side of the gunite pool or in the wildflower gardens.

But for those with more of a business focus in mind, the estate could also be viewed as a potentially lucrative investment for one savvy buyer, with the listing noting that its 12 acres of land have “already been subdivided into five lots, creating a unique opportunity to enjoy the estate as one spectacular compound or the ability to sell off additional parcels in the future.”