When you think of the man behind Tony Stark, you probably imagine a world of high-tech gadgets, sleek, minimalist skyscrapers, and cutting-edge industrial design. But if you take a peek behind the curtain of Robert Downey Jr.’s personal life, you’ll find that his taste in architecture is far more whimsical than the futuristic labs of Iron Man. Deep in the heart of East Hampton, New York, sits one of the most eccentric, charming, and historically rich pieces of real estate in the celebrity world: the Edward DeRose Windmill Cottage.
In 2017, Downey Jr. and his producer wife, Susan Downey, made headlines when they dropped $10.5 million on this 141-year-old architectural oddity. It wasn’t just another high-end mansion in the Hamptons; it was a slice of 19th-century history that felt as though it had been plucked directly from a Grimm’s fairy tale.
A Whimsical Investment in East Hampton History
Built in 1885, the Edward DeRose Windmill Cottage is a far cry from the glass-and-steel modernism that defines much of today’s luxury real estate. The property was originally commissioned by wealthy businessman Edward DeRose, who acquired the land from Jeremiah Miller. At the time, the “windmill style” was the height of fashion for Long Island’s elite. DeRose envisioned a Victorian summer home that wasn’t just a place to sleep, but a statement piece on his expansive ‘Millfield’ estate.
The structure is anchored by a faux windmill—a design choice that is as functional as it is aesthetic. In its original heyday, the windmill tower served as the home’s foyer, library, and office. It wasn’t long before the structure became a local landmark, drawing eyes for its unique silhouette. Over the decades, as the property changed hands, it underwent several expansions, ballooning from a quaint cottage into a full-scale residential compound. By the time Downey and his wife set their sights on the property, it had already been transformed into a sophisticated sprawling estate, yet it still retained that quirky, storybook soul that clearly captured the actor’s imagination.
From Silver Screen Star to Real-Life Residence
The cottage isn’t a stranger to the spotlight. In fact, for those who love cinema, the house might look vaguely familiar. In the 1980s, the property gained a certain level of cult fame when director Sidney Lumet chose it as the primary setting for the 1982 mystery thriller Deathtrap. Starring Michael Caine and Christopher Reeve, the film utilized the eerie, eccentric architecture of the windmill to heighten the suspense and atmosphere of the story.
By 1998, the home had undergone significant modernizations. The estate expanded to an impressive 8,500 square feet, sitting on four sprawling acres that boast everything a modern A-lister could desire: manicured gardens, a sparkling pool, a professional-grade tennis court, and a cozy guest house. It was a well-oiled machine of a luxury property by the time the Downeys moved in, but the couple wasn’t interested in living in a museum. They wanted to make it theirs.
A Six-Week Masterclass in Interior Renovation
When you have the resources of an Avenger, you don’t spend years agonizing over paint chips. Shortly after closing the deal in 2017, Downey Jr. enlisted the talents of famed interior designer Joe Nahem to strip away the dust of the past and inject some high-octane personality into the home. What followed was a dizzying, six-week sprint to revitalize the entire interior.
The result is a masterclass in “eccentric chic.” Upon entering, guests are greeted by a bold, rainbow-striped wallpaper that immediately sets a playful tone. The living room, intentionally redesigned to sit lower than the entryway, offers a sunken, intimate feel that contrasts sharply with the soaring verticality of the windmill exterior. The centerpiece of this room is a custom-made, ceramic wraparound fireplace created by artist Peter Lane—a tactile, organic addition that feels both ancient and contemporary.
The bedrooms lean into a more serene, high-end aesthetic, with all-white palettes and ivory-hued accents, but the home never loses its sense of humor. One room features a massive, striking portrait of crashing ocean waves paired with golden-hued sofas and warm, polished wood floors, creating a space that feels like a refined art gallery.
The Exterior: Where Modern Luxury Meets Storybook Charm
If the interior is a curated collection of art, the grounds of the Windmill Cottage are a playground for the imagination. The Downeys have embraced the “eccentric” label in every sense of the word. Beyond the pool—which is equipped with a personal bar and a full outdoor TV setup for those late-night movie marathons—the landscape is dotted with strange and wonderful sculptures.
Perhaps the most famous resident of the garden is the massive green praying mantis statue that stands guard near the entrance. It’s a whimsical, slightly surreal touch that perfectly encapsulates the couple’s approach to their home: it shouldn’t just be expensive; it should be fun.
The outdoor dining area, anchored by a vibrant mosaic table, speaks to a life well-lived. Whether they are hosting A-list friends or enjoying a quiet morning with their children, the space is designed for comfort without ever taking itself too seriously. It’s a home that reflects Robert Downey Jr.’s own career trajectory—full of surprising twists, historical significance, and a whole lot of personality.
In a neighborhood defined by understated, monochromatic Hamptons mansions, the Edward DeRose Windmill Cottage remains a standout. It is a reminder that even at the height of global fame, the best kind of luxury is the kind that makes you smile when you walk through the front door.
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