Inside the Sears Family’s $6 Million Hudson Valley Estate

Before Walmart and long before anyone dreamed of Amazon’s “Prime Day,” there was Sears, Roebuck & Co. The company’s famous catalog brought everything from washing machines to entire mail-order houses right into American homes. And while millions of families lived with Sears as their de facto department store, the family behind the empire had their own slice of Hudson Valley heaven. And that very estate, a sprawling 106-acre property known as Rolling Stone Farm, has just hit the market for $6 million.

The home was built in the early 1930s for Adele Rosenwald Levy, the daughter of Julius Rosenwald, who transformed Sears into a retail powerhouse and one of the most influential businesses of the 20th century. Adele married Dr. David M. Levy, a pioneering psychiatrist who introduced the Rorschach Inkblot Test to the United States. Together, they built the ultimate countryside retreat in Croton-on-Hudson, just 37 miles north of Manhattan.

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At its center is a European-style stone-and-shingle manor, brimming with architectural details that recall another era: leaded-glass windows, wide-plank floors, bullnose plaster walls, and a slate-tiled foyer. The wood-paneled living room comes with French doors and a fireplace, while the primary suite upstairs includes vaulted ceilings, a marble bath, and a walk-in closet.

But Rolling Stone Farm is more than just a grand home—it’s a patchwork of eccentric, storybook touches. Dr. Levy’s personal octagonal stone library still stands, a whimsical building that feels like something out of a children’s novel. There’s also a two-bedroom cottage with brick floors and a double-height living room, plus a smaller outbuilding that has the unmistakable vibe of “Hagrid’s hut.”

Outside, the grounds are equally enchanting. Formal English gardens and ancient specimen trees give way to riding trails that connect directly to the Croton Aqueduct path. Once home to more than 20 horses, the equestrian facilities remain impressive: an 1800s bank barn, groom’s quarters, paddocks with run-in sheds, and an outdoor arena. Non-riders can take to the tennis court, the 45-foot gunite swimming pool, or one of the many stone terraces.

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The estate has been privately owned for the past 25 years but still retains the sense of grandeur—and privacy—that defined it when the Rosenwalds and Levys were in residence. Rolling Stone Farm last sold in 2000 for $2.25 million. Now, nearly a century after the Sears family first built it, the estate is looking for its next chapter.

“Opportunities like this are incredibly rare… a storied estate of this scale and caliber, just outside New York City,” says Will Stuart of Berkshire Hathaway HomeServices, who holds the listing. “The history, the privacy, the land itself…when you’re out here, standing on the grounds and immersed in that kind of quiet and natural beauty, it really does stop you in your tracks. You feel worlds away.”

Click here to see more photos of this Hudson Valley estate.