5 Waterfront Estates and Elite Retreats Across South Florida

Along the Atlantic Ocean at Mile Marker 22 in Cudjoe Key, Casa Aqua unfolds across 16 pristine waterfront acres, offering a rare sense of seclusion just 30 minutes from Key West. The Spanish Mediterranean estate is designed for unhurried days framed by turquoise water views and breathtaking sunsets. The main home spans 12 acres and includes five bedrooms and 3.5 baths, paired with a proven 18-year rental history that speaks to its enduring appeal. A separate guest cottage—with a loft suite—sits on two additional acres and opens to panoramic views, creating a natural retreat for visitors or extended stays. With transient rental licenses allowing nightly and weekly rentals, the property carries the quiet flexibility of a private estate with boutique-resort potential.

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Along the water’s edge on Crescent Beach, 11 Sunset Key Drive offers a fully renovated retreat on Sunset Key, a private island in the Florida Keys accessible exclusively by private ferry. Completed in 2018 with over $1.7 million invested, the nearly 3,000-square-foot residence was rebuilt for easy island living, with hurricane-impact doors and windows, an updated roof, all-new electrical, white oak engineered wood flooring, a new interior fire suppression sprinkler system, and fresh interior and exterior paint. In the kitchen, a Sub-Zero refrigerator anchors new stainless appliances, new countertops, and custom cabinetry. Outdoors, a private pool and spa were rebuilt down to the plumbing with handcrafted, hand-painted tile, updated equipment, a heater, LED lighting, and app-controlled features. Fully furnished by Restoration Hardware, life here unfolds between private beaches and Sunset Key’s oceanfront restaurant, spa, fitness center, and tennis courts.

Along the Intracoastal in Fort Lauderdale, this contemporary waterfront estate spans 100 feet of deep water with direct access and no fixed bridges. Inside, Italkraft chef and butler kitchens anchor daily living, equipped with Sub-Zero, Wolf, and Dacor appliances and Level 5 quartz. A 1,000-bottle wine room adds a collected, evening-ready note, while a private gym, Lutron smart home system, 18-speaker audio, four-zone A/C, and a Kohler 38K generator with a 1,000-gallon propane tank support effortless hosting. Porcelain baths and floors downstairs transition to European oak upstairs, connected by a floating walnut staircase and stainless-steel elevator. Eleven- and twelve-foot collapsible sliding doors extend the living areas outdoors to a heated saltwater pool and spa, custom outdoor kitchen, and a concrete dock with power pedestal and dolphin piles—offered fully furnished for an easy arrival.

Along the water’s edge on Islamorada’s iconic Old Highway, Casa Mar Azul unfolds as a one-of-a-kind oceanfront estate with 200 feet of Atlantic shoreline and a private jetty with dockage. Inside, an open floor plan is crowned by soaring vaulted tongue-and-groove ceilings, while floor-to-ceiling windows and doors draw the horizon into the airy living space. An expansive open terrace extends the day outdoors, framing unobstructed ocean views and steady sea breezes. Upstairs, two spacious bedrooms and two full baths are arranged for comfort and ease. A versatile bonus room opens to a covered lanai that leads directly to a sandy beach—an effortless setting for quiet mornings or lingering evenings. Mature tropical landscaping adds a welcome sense of seclusion, with Islamorada’s restaurants, boutiques, and art galleries just a short walk or bike ride away.

Within the heart of Pinecrest along one of its most desirable corridors, this gated estate sits on a lush acre-plus lot, balancing privacy with easy access to top schools, parks, and the best of Miami living. Inside, seven bedrooms plus a private office include a ground-floor primary suite overlooking the pool, finished with soaring ceilings, designer lighting, and two oversized walk-in closets. The marble primary bath pairs a soaking tub with an oversized shower ready for a steam system. At the center, a chef’s kitchen features Thermador refrigeration, a gas range, double ovens, a hidden pantry, and a breakfast nook, flowing into a spacious great room with fully retractable doors for true indoor-outdoor ease. A game room with full bar and cabana bath, temperature-controlled wine cellar, and multiple laundry areas complete the entertaining-ready plan, while a cylindrical elevator adds a sculptural touch. Outdoors, a heated saltwater pool, propane fireplace, twilight landscape lighting, and expansive grounds set the tone for evenings at home.