Inside a One-of-a-Kind Islamorada Estate That Redefines Coastal Living

Lucía Torres · 2026-07-22

When you think of Islamorada, you probably picture classic beachside bungalows and laid-back fishing shacks. But at 19 Avacado Street, something completely different rises from the shoreline. Custom-designed by the award-winning Charles Vincent George Architects, this waterfront estate is a bold departure from the norm. It's all poured concrete and floor-to-ceiling glass, with panoramic sunset views over Florida Bay that'll stop you in your tracks. The property sits on 1.27 private acres across two parcels, making it one of the most coveted bayfront addresses in the area. Represented by Lisa Swanson of The Agency, this 5,489-square-foot home feels more like a coastal modernist retreat than anything else in the Keys. It's contemporary design meets the easy-going seaside lifestyle, and the combination is pretty special. ### A First Impression That Sticks As you walk up, palm and fruit trees line the path in a way that feels both native and intentional. It sets the tone before you even reach the door. Inside, a floating staircase anchors the main living area, and those 12-foot doors give the ground floor a grand sense of scale. Engineered hardwood runs underfoot throughout, and the finishes stay quiet. They let the architecture and the views take center stage. ### Open Living, Unobstructed Views The open floor plan flows straight from the foyer to the bayside. The kitchen, dining room, and family room all share floor-to-ceiling retractable glass, so you're never far from the water. The minimalist kitchen is built around quartz countertops and a full Miele and Thermador appliance package. There's even a hidden walk-in pantry tucked out of sight to keep the main space clutter-free. ### First-Floor Primary Suite and Guest House A first-floor primary suite offers comfort and accessibility, with full views of the 50-foot saltwater lap pool and the bay beyond. A large picture window floods the expansive primary bath with natural light, where you'll find a standalone tub and dual sinks. A generous walk-in closet sits just across the hall. The primary suite shares an outdoor patio with a separate 1-bedroom, 1-bath guest house. That gives you a fully private space for family, staff, or overflow guests without borrowing any square footage from the main house. ### Upstairs Flexibility Upstairs, you'll find three additional private ensuite bedrooms (two with balcony access) and a large bonus room that opens onto a turfed-lawn deck facing the bay. This flexible fourth space can shift roles depending on who's staying. It could be a media room, a home office, or an extra lounge. ### Outdoor Living at Its Best The outdoor patio is designed for resort-caliber relaxation. A sculptural gateway echoes the home's cantilevered architecture, and the amenities are seriously impressive: - Elevated heated and chilled saltwater lap pool - Private sandy beach area - Entertaining terraces - Mature tropical fruit trees - Air-conditioned garden shed - Gated entrance for exceptional privacy The protected boat basin features a composite dock and a 12,000-pound boat lift, plus immediate access to world-class fishing and diving. At the front, there's an oversized air-conditioned garage with EV charging and a half bath. A covered carport sits adjacent to the main house. ### The Takeaway 19 Avacado Street is more than just a home. It's a rare chance to own one of the Florida Keys' premier contemporary bayfront estates. The combination of exceptional architecture, outstanding construction, and those spectacular sunsets is hard to beat. For more information or to schedule a showing, reach out to Lisa Swanson at The Agency.