This South of the Highway estate has everything in place for a luxurious and private Hamptons escape. Secluded at the end of a long flag lot drive and set on an expansive 4.6-acre parcel, the property unfolds like your own personal resort. Mature, manicured plantings create natural privacy and a sense of timeless beauty, surrounding a full basketball court, a separate tennis court, and curated outdoor living areas designed for recreation, relaxation, and elegant entertaining. A detached 3-car garage with a turnaround drive offers ample parking for guests, while the garden-lined arrival leads to the traditional home. A welcoming covered front porch leads into bright interiors, with tall ceilings and a stunning curved staircase. The home's formal dining room features rich hardwood floors, ideal for gathering over memorable meals. Just beyond, the great room serves as the central gathering space, with a curated view of the estate's most striking specimen plantings framed by near floor-to-ceiling windows. This generous space includes a built-in bar for effortless entertaining and a wood-burning fireplace for added warmth and ambiance. The eat-in kitchen is designed for both functionality and elevated daily living, outfitted with premium appliances, custom cabinetry, and generous counter space. The kitchen flows seamlessly into a sunlit dining area, perfect for informal meals and morning coffee with views of the lush rear grounds. A first-floor primary suite offers a private retreat, complete with a walkout sitting room that opens directly to the poolside patio. Outside, the patio is a true extension of the living space, perfectly scaled for Hamptons summer living. A covered pergola dining area invites al fresco gatherings, while the freeform pool, with its custom attached spa, is bordered by stonework and garden beds. A stylish pool house with large sliding glass doors provides a secondary indoor-outdoor venue for leisure or entertaining. Upstairs, an additional living room lounge is bathed in natural light beneath skylights. Three well-appointed ensuite bedrooms provide comfort and privacy for loved ones and weekend guests. The exterior grounds are a masterclass in Hamptons landscape design, offering a variety of cultivated vignettes for quiet conversation and athletic pursuits, all with garden views. The full-court basketball court and tennis court are thoughtfully positioned and separated by a pergola viewing pavilion. Located in a premier South of the Highway setting, this estate offers proximity to world-class ocean beaches, renowned farmstands, and the charm of nearby Villages. A private compound with resort-like amenities and a layout designed for elevated indoor-outdoor living, this offering captures the essence of the Hamptons lifestyle.