9 Old Montauk Highway, deep flag lot Experience the best of Amagansett living in this exquisite classic residence, thoughtfully designed for both refined comfort and effortless entertaining. Encompassing approximately 4, 700 square feet, this 5-bedroom home by John Hummel & Associates seamlessly blends timeless architecture with modern amenities and elevated finishes throughout. Privately sited down a deep, gated flag lot, the property unfolds into a beautifully landscaped setting of lush gardens, mature trees, and an expansive lawn-creating a rare sense of seclusion and a truly magical outdoor oasis. Inside, a dramatic double-height living and dining room anchored by a wood-burning fireplace is bathed in natural light, offering an airy and inviting atmosphere ideal for both intimate gatherings and larger-scale entertaining. The gourmet kitchen is appointed with top-of-the-line appliances, generous counter space, and effortless flow to the main living areas. Just beyond, a screened porch overlooks the pool, offering a seamless extension of indoor-outdoor living-perfect for morning coffee or evening unwinding in every season. The first floor features a luxurious primary suite, along with an additional en-suite guest bedroom, providing both privacy and convenience. Upstairs, two additional bedrooms and a charming balcony overlook the serene backyard, creating a peaceful retreat for family and guests alike. The finished lower level adds exceptional versatility, featuring a spacious playroom, guest bedroom, laundry room with two sets of washers and dryers, a wine cellar, and cedar closet. Outdoors, the property is designed for resort-style living, complete with a gunite pool and spa, outdoor shower, fully equipped outdoor kitchen, and thoughtfully integrated exterior lighting that transforms the grounds into a warm and inviting evening setting. A detached garage provides additional storage and convenience. Whether as a year-round residence or a summer escape, this Amagansett hidden gem is moments from pristine ocean beaches, farm stands, the village, and iconic Amagansett Square-offering a rare opportunity to own in one of the Hamptons' most coveted enclaves.