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$3,800,000

Tired of waiting on Uber or Freebee? Why not make this stunning bayfront estate your own private slice of paradise, right in the heart of Islamorada? Just a flip-flop stroll away from local favorites like MEAT Eatery, Shima, Marker 88, and City Hall Café, this property places you at the vibrant core of island living. Behind its private, fully fenced grounds, you'll discover sweeping bay views and a rare tiki hut at the end of the dock—your new go-to spot for toasting unforgettable sunsets. Upstairs, the open-concept living area spills out through sliding glass doors onto a spacious, screened-in terrace, perfect for laid-back evenings or lively gatherings. This level also features three bedrooms and two baths, providing plenty of space for guests or family. Step down from the terrace to your own tropical oasis, complete with a pool, backyard, beach, and dock. The ground floor adds even more flexibility with two additional bedrooms, a bath, and a relaxed living area—ideal for guests or extended family. Whether you're looking for your forever getaway in the Keys or a smart investment when you're not soaking it all in yourself, this property is a rare find. Come see why life really is better by the bay.

5 Beds ⋅ 3 Baths ⋅ 618165 MLS

87950 Overseas Hwy, Islamorada

$18,999,000

The Oasis Islamorada is a waterfront estate of exceptional scale, conceived as a private Florida Keys compound where architecture, land and water come together spanning nearly 3 meticulously landscaped acres. More than 400' of shoreline, sweeping ocean views and a protected deepwater basin create a marine setting rarely available within a single residential offering. Beyond the grand porte-cochère, the single-level main residence unfolds with soaring ceilings, white oak floors and 12-foot retractable glass walls that dissolve the boundary between interior and oceanfront living. At its center, a chef's kitchen pairs a cascading Calacatta marble island with Thermador appliances and a walk-in pantry, opening seamlessly to expansive living and dining spaces. The main residence includes four bedrooms and six full baths, with an impressive primary suite featuring a fireplace, dual walk-in closets, safe room and spa bath with steam shower. Additional suites offer en suite baths, private balconies and ocean views. A detached two-bedroom, two-bath guest residence brings the estate to six bedrooms while preserving privacy between owners and guests, with substantial grounds offering extraordinary flexibility for the future. Outside, the property assumes the scale of a private resort. Two resort-style pools with spas and sun decks are joined by a summer kitchen, alfresco dining and multiple waterfront terraces. A fitness center with sauna, soundproof theater and golf simulator complete the lifestyle offering. For the yachtsman, the protected deepwater basin accommodates substantial vessels with convenient direct Atlantic access. Built with an uncompromising focus on quality, security and enduring construction, The Oasis is more than an oceanfront residence. It is a legacy-scale Florida Keys estate offering the increasingly rare combination of acreage, significant shoreline, protected deepwater dockage, multiple residences and complete privacy within one extraordinary property

6 Beds ⋅ 8 Baths ⋅ 615643 MLS

87429 Old Hwy, Islamorada