Nestled between the Atlantic Ocean and Georgica Pond lies a storied property synonymous with Hamptons history. The 8.22-acre two parcel compound has changed hands just three times despite being one of the first properties developed in the Georgica Dunes, with each owner treating the estate as a sacred trust - honoring its remarkable legacy while elevating its elegance. The offering comes with the last vacant buildable oceanfront parcel in the Village. Among the landscaped grounds, you'll discover over 500 feet of ocean frontage, unobstructed views, the last working boathouse on the pond, a red clay tennis court, a nearly 9000-square-foot main residence, and room for additional habitable structures. With award-winning design, bespoke craftsmanship, and a provenance that reads like a chapter of American cultural history, this is an unmatched residence ready to greet its next generation of proud stewards. Completed in 1894 by Laura Brevoort Sedgwick James, the residence is thought to be one of the oldest on the Georgica Dunes. In 1935, Juan Trippe, founder of Pan American World Airways, acquired the home and expanded the compound. In 1981, the property was sold to fashion designer Calvin Klein and his wife, Kelly Rector Klein, who launched a meticulous transformation of the home under renowned French architect Thierry Despont. The residence is a classic Shingle Style abode featuring gambrel roofs and over 5,000 square feet of decks, patios, and gardens for seamless indoor-outdoor living. Inside, the showplace expertly pairs glamorous contemporary design with original elements for a timeless aesthetic spanning more than a century of elegant living. Soaring beamed and coffered ceilings rise above original wide-plank pine, new oak, imported French stone, custom millwork and eight fireplaces. A gracious foyer with a two-story metal fireplace makes a dramatic first impression, while the formal dining room sets the stage for lavish entertaining. Linger in the charming tearoom, or gather in a living room topped by a glass catwalk or enjoy all-season enjoyment of the surrounding landscape in the attached screened-in porch. Entertaining is effortless with a main kitchen, prep kitchen and staff kitchen equipped with La Cornue, Viking and Sub-Zero appliances. A chic bar/lounge keeps refreshments within easy reach. Across the deck, the iconic tower is a retreat within a retreat featuring a curved staircase, a dome, a family room with its own wet bar, and a private bedroom suite above. The home's upper level includes a palatial owner's suite featuring a fireplace, two bathrooms with walk-in closets, and access to a large deck. Three secondary suites enjoy water vistas, while a study and wraparound decks complete the top floor. The thoughtfully appointed lower level - complete with a sixth bedroom suite, staff quarters, mudroom, laundry and sauna - ensures the estate runs effortlessly. Extensively updated for modern living, the residence boasts new hurricane-rated windows and doors, geothermal systems, a generator, fully integrated security and smart home automation. Thanks to its unrivaled location, the sanctuary commands virtually unimpeded, 360-degree views from dawn to dusk. Enjoy sunrise strolls on the beach, take a sunset paddle on the pond, and perfect your backhand on the clay tennis court featuring a viewing terrace. Garden paths amble past irrigated landscaping, native plantings and fountains, while the outdoor shower rinses sandy toes and paws. An automated entry, locked garden gates, a four-car garage, and ample parking complete the property. Alongside the tennis court, you'll find the ideal setting for a two-bedroom guest cottage and pool/spa addition. On the adjacent 1.89-acre parcel, architectural plans envision a three-story residence with a garage.