Tucked away on a quiet dead-end street in an executive-style neighborhood in Port Jefferson Station, this Hamptons-inspired contemporary home offers exceptional privacy and resort-style living. Featuring approximately 3,207 sq ft, this 5-bedroom, 3.5-bath residence showcases a dramatic great room with soaring 20-foot ceilings, expansive windows, and skylights that flood the space with natural light. A lofted second-floor media room overlooks the great room and offers potential for a fifth bedroom or additional flexible living space. The first-floor primary suite provides direct access to the deck and backyard oasis, while a dedicated home office off the foyer is ideal for remote or hybrid work. Designed for entertaining, the resort-style backyard features an in-ground pool, cabana, expansive deck, and retractable SunSetter awning. Additional highlights include a fully landscaped 0.59-acre property with specimen trees, three-zone heating and central air conditioning, high-efficiency Andersen windows, central vacuum, six-zone irrigation system, and a full unfinished basement offering future expansion potential. A built-out area offers strong potential for a future accessory apartment (subject to township approvals). This home offers a rare blend of architectural style, flexibility, and everyday luxury.