Inside Tommy Hilfiger’s Grand Greenwich Getaway

While Tommy Hilfiger and his brand are practically synonymous with sophisticated, often sporty, but relentlessly classic American style, the majestic Greenwich compound the acclaimed fashion designer and his wife, Dee, have owned and updated over the last three years is the epitome of Old World elegance and refinement.

Greenwich, Connecticut | Janet MilliganSotheby’s International Realty – Greenwich Brokerage

At the heart of the gated 22-acre estate is a stunning French Normandy-style residence, which dates to the 1930s and has been home to a real estate magnate and a renowned art collector. Beyond a storybook façade of granite and Holland brick clad in impeccably groomed ivy, a roofline of Ludowici tile custom-crafted in Turkey, and a stately turret, rooms are distinctively detailed and generously proportioned—the interiors measure a remarkable 13,344 square feet. The home’s heritage and unique original finishes have been carefully, respectfully retained, while superior modern amenities and conveniences have been discreetly added.

The great hall impresses with eye-catching ceiling treatments, intricately embellished and richly hued woodwork, an ornate oversized fireplace, and a dramatic carved oak staircase set in a leaded-glass bay, its graceful curves connecting each of the home’s three levels. Beyond is a handsome library with a tracery ceiling and a sunny bay window. Suitable for grand banquets, the formal dining room features a fireplace and walls finished in Tudor-style paneling and wool upholstery; in an ideal flow for indoor-outdoor festivities, the room gives way to a terrace. Spacious and open, the kitchen offers an oversized marble-topped island with counter seating for four, furniture-grade cabinetry, zinc counters, and professional-caliber appliances from Wolf, Sub-Zero, Miele, and others. With the airy, light-flooded feeling of a solarium, the family and billiards room—made more inviting by a full-service bar and an 18th-century French fireplace—opens on two sides to terraces and gardens. The luxurious home theater boasts striking hand-painted Turkish-influenced fabric wall treatments.

The chic owner’s suite—one of six bedrooms in the home—features a warming fireside sitting area, cashmere-upholstered walls, a Juliet balcony, a bath with a steamshower and tub, a lavish dressing room, and—secluded at the top of a private en suite stairway—a second dressing area, an office or study, and a morning bar. The estate is a self-sufficient oasis, also offering a wine cellar and tasting room, a mirrored and windowed fitness studio, a whimsical playroom, and a spa-inspired massage room that includes a bath with a steamshower and a sauna. Visitors will appreciate the consummate privacy of the one-bedroom third-level guest apartment, which provides sitting and dining rooms, a kitchenette, and a lovely bath.

Celebrated landscape architect Miranda Brooks created manicured grounds that envelop the home in an alluring expanse of emerald. Nearly every first-floor room of the residence opens to this diverting collection of boxwood and privet hedges, shade trees, tranquil fountains, rose and topiary gardens, wisteria-draped pergolas, a koi pond, and lush lawn. Outdoor enjoyment is effortless thanks to a compelling variety of terraces, an updated tennis court, and a refreshing swimming pool. The home shares the acreage with a two-bedroom guest cottage, a detached four-car garage, and a greenhouse. The property benefits from a coveted prime position at the top of Round Hill Road, which affords it an outlook that stretches across Long Island Sound, at night revealing the dazzling skyline of Manhattan.

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