Welcome to a rare offering in the heart of the Florida Keys—this 1.65-acre gated bayfront compound in Islamorada combines timeless island luxury with modern amenities and endless water views. With 150 feet of private waterfront, dockage, boat ramp, private beach, two pools, and lush, mature tropical landscaping, this estate is a true Keys sanctuary. The 7,562 sq ft main residence boasts 5 spacious bedrooms, 6 full bathrooms, an office, and exquisite finishes throughout. The gourmet kitchen features marble and dolomite countertops, a custom mosaic tile backsplash, a built-in Miele coffee system, a wine tap, a 36'' Wolf gas cooktop, four Sub-Zero refrigerators, and two laundry rooms. A stunning 180-bottle glass wine cellar, a handmade wood bar with a wood sink, a Sonos sound system, and a media-ready living room with blackout shades enhance the entertaining potential. Additional highlights include an elevator, Lutron lighting system, Toto toilets, expansive covered porches with panoramic open bay views, an outdoor kitchen complete with Italian brick pizza oven, flat grill, and smoker, as well as a tackle room and 4-car garage. The 2,666 sq ft guest house offers a private gated drive, 3 bedrooms, 4 bathrooms, a private pool, and a fully equipped kitchen with JennAir appliances, making it ideal for hosting guests or extended family in complete privacy. With two gated driveways, serene lawns, and a high-end tropical ambiance, this estate seamlessly blends privacy, prestige, and paradise. A one-of-a-kind legacy property - experience the ultimate Florida Keys lifestyle.