This extensive and exquisitely crafted multi-home estate is steeped in Sagaponack's rich history and comes equipped with full approvals and plans from a renowned Hamptons designer. Originally named the Greenridge Cottage, this is truly a statement property epitomizing the Hamptons' past, present, and future. With generous acreage, there is ample room for expansion and tennis, and recent renovations have expertly expanded the property to offer 9 bedrooms across the 3 stunning structures-a handsome main home, a large guest home, and a guest cottage. Originally constructed in 1899 by the renowned NY architectural firm of James E Ware & Sons for John G. Deshler's family, one of the area's earliest summer residents, this desirable estate is now available for only the second time in its long history. With 4.5 +/- bucolic acres, privately secluded on the iconic Sagg Main Street, this compound's approach includes a teak-gated entrance leading to a half-circle driveway and a charming porte-cochère set in front of the house. The estate boasts unparalleled charm and features a gambrel-roofed main home with a front foyer that leads to a sun-filled open living space complete with a wood-burning fireplace and views of a rolling green lawn bringing the outdoors in. The first floor includes an eat-in kitchen with an open floor plan boasting premium appliances, custom cabinetry, and an inviting breakfast nook with built-in bench seating. Adjacent, a formal dining room is ready for elegant entertaining with convenient service from a rustic, Manhattan-style built-in bar and butler's pantry. The sunroom beams with light and open agricultural views from a striking wall of windows and opening to a large patio bookended by two magnificent mature planted Norwegian oaks. A graceful staircase leads to the second floor, where the spacious ensuite primary bedroom and den feature a fireplace and fully renovated luxe bathroom. Additional bedrooms, a home office, artisan-crafted built-ins, walk-in closets, another fireplace, and a renovated bathroom complete the second floor. The third floor is highlighted by a white wood-paneled living space with two additional bedrooms and a bathroom. The compound is surrounded by mature landscaping, complemented by a dining gazebo, covered patio, potting shed, cottage, and guest house. The gracefully appointed guest house is highlighted by a charming living room wrapped in built-ins and cathedral ceilings, plus 2 bright bedrooms and a full bath, kitchen, ample living space, fireplaces, patios overlooking the lush grounds, and an attached 2-car garage. The separate cozy guest cottage adds another bedroom, full bath, and attached studio space. A gardener's dream, the property is complete with an abundance of perennial flowers, manicured hydrangea beds, and a vegetable garden. The expansive estate is conveniently located near farm stands, Bridgehampton Village, and pristine ocean beaches. Ready for immediate move-in, you'll have the opportunity to live in the luxurious guest home while expanding the main home. Honoring the home's contribution to Hamptons' history, designs by Michael Davis are an extension of the property's character and charm, elegantly evolving the home into a masterclass of Hamptons luxurious lifestyle.