Welcome to 45 Whippoorwill, a stunning coastal retreat that perfectly blends indoor luxury with effortless outdoor living. Nestled on a beautifully landscaped, park-like acre, this expansive and light-filled home offers the ultimate in elegance, comfort, and privacy. Once inside you'll discover a bright open-concept layout designed for both entertaining and relaxed everyday living. The expansive great room features soaring ceilings, a large wood-burning fireplace, and multiple sliders that open to an oversized deck with views to the pool and court, creating a seamless transition to the outdoors. With multiple seating areas throughout, this home is thoughtfully designed to host gatherings of any size or to simply unwind in comfort. Outdoors, enjoy resort-style amenities including a heated pool, hot tub, Har-Tru tennis court, and a fabulous built-in outdoor chef's kitchen - all perfect for year-round entertaining. At the heart of the home is a large, fully equipped chef's kitchen featuring extensive counter space, two working islands, and double counter seating - ideal for casual meals or entertaining with ease. The kitchen flows effortlessly into the open dining area, creating a welcoming and connected living space. There are four (convertible to five) spacious bedrooms and six full baths, including two luxurious en-suite primary suites - one conveniently located on the first floor with direct deck access, and another upstairs featuring its own private deck with evergreen sunset views. A full basement offers endless potential for recreation and entertaining. Enjoy west-facing sunset views over the Quogue Wildlife Refuge, along with the benefit of low Quogue taxes - making this property as smart an investment as it is beautiful.