For Donna Lennard, owner of the renowned Il Buco hospitality empire, finding the perfect Hamptons haven was a labor of love that spanned years and millions. But the payoff was a luxurious waterfront oasis tailored to her exacting tastes. When Lennard set her sights on the bucolic hamlet of Springs in 2017, she knew precisely where she wanted to put down roots – the enviable Gerard Drive peninsula jutting into both Gardiners Bay and Accabonac Harbor.

“From one side to the other, you see water,” gushes the entrepreneur over 50. Her gambit paid off when a 1,700 square foot cottage from 1960 hit the market. Swooping in with an all-cash $1.7 million offer, Lennard made the keys her own that August. But for the hospitality magnate behind hotspots like Il Buco Alimentari & Vineria, the dated digs wouldn’t do. A serendipitous reunion with college pal and architect Stuart Basseches set the wheels in motion for a start-to-finish overhaul that snowballed into a head-turning $3 million investment.

Over several years of meticulous planning alongside Basseches, Lennard’s original concept for a bedroom addition morphed into a full-scale transformation. The reimagined floor plan fuses old and new – relocating the light-filled kitchen and living room to the heart of the residence while tacking on a striking 1,100 square foot two-story extension housing a dining room, media lounge and lavish upstairs owner’s suite. No expense was spared in the bespoke finishes. Sun-drenched living spaces boast reclaimed oak floors, vaulted wood-beamed ceilings and artisanal Venetian plaster walls.

The showstopping kitchen island crafted by Sakonnet Furniture Makers tops a slab of repurposed Slovenian wood. And the serene upstairs retreat flaunts an antique Umbrian marble sink alongside a mobile vanity revealing dreamy water vistas. While the splurge surpassed her original budget, for Lennard, the over-the-top transformation was well worth it. “What came out of it was very much the house I’d been dreaming of,” she confides of her ultra-luxe oceanside compound expertly melding modern amenities with an eclectic, lived-in aesthetic reflective of her well-traveled tastemaker persona.