30 John Street in Greenwich, CT: Tommy Hilfiger’s $45 Million French Normandy-Style Manor

Set atop one of the most scenic vantage points in Greenwich, CT, with expansive views of the Manhattan skyline and Long Island Sound, Tommy Hilfiger’s former Round Hill estate recently sold for $45 million.

This ivy-clad, 13,344-square-foot French Normandy-style manor spans 22 acres in Greenwich. The residence offers six bedrooms, seven bathrooms, and three powder rooms. Architectural elements include carved oak staircases, intricate plasterwork ceilings, and six antique fireplaces. A Turkish-inspired screening room, adorned with hand-painted fabric walls, draws inspiration from palace tiles in Istanbul. The billiards lounge, featuring limestone and wood inlays, complements the wine cellar and tasting room, creating a refined setting for leisure and entertainment.

But the estate isn’t just about grandeur—it’s designed for entertaining. Outdoors, a grass tennis court, heated pool, and expansive park-like lawns offer an ideal setting to unwind. Landscape architect Miranda Brooks designed a series of gardens, featuring a fountained rose garden, a koi pond, and intricate boxwood hedges. The guesthouse includes a living room, kitchen, and two bedrooms, while additional amenities include a four-bay garage, a greenhouse, and a converted teahouse-turned-security pavilion.

Ownership Through the Decades

Originally built in 1939 by Charles V. Paterno, a New York City real estate developer, Round Hill was designed as a secluded country retreat. Later, the estate became home to financier and art patron Joseph H. Hirshhorn, the namesake of the Hirshhorn Museum in Washington, D.C. Decades later, it was owned by business attorney John V. Holten, who sold it in 2010 to Hilfiger and his wife for $31.4 million.

When Hilfiger and his wife purchased Round Hill, the estate had fallen into significant disrepair. Over the next three years, they restored the home, overhauling its mechanical systems, rewiring the entire estate, and updating the plumbing and ventilation. The original terra-cotta roof tiles, too unique to replace off the shelf, were specially commissioned from a manufacturer in Turkey to match the originals.

The couple preserved the original wide-plank floors, enhanced moldings and ceilings, and added a new chef’s kitchen and modernized baths. The home’s décor incorporates influences from their extensive travels, combining antique fireplaces with Swiss and Austrian hunting lodge motifs, including antler chandeliers and outdoor animal statues—a nod to the estate’s history as a former deer and fox-hunting property.

While Hilfiger is known for buying, restoring, and selling Greenwich estates, his decision to sell Round Hill aligns with a broader lifestyle shift. He and his wife relocated to Palm Beach—a move accelerated by the pandemic and Florida’s tax advantages.