Inside Islamorada's Most Unexpected Waterfront Estate

Lucía Torres · 2026-07-22

Most homes in Islamorada lean into the whole beach-bungalow thing. You know the look: pastel shutters, a bit of driftwood decor, and that laid-back Keys charm. But every once in a while, a property comes along that flips the script entirely. That's exactly what you'll find at 19 Avacado Street. Custom-designed by the celebrated team at Charles Vincent George Architects, this poured-concrete estate is a bold departure from the norm. It's got more in common with coastal modernism than traditional island architecture, and honestly, that's what makes it so compelling. ### A First Impression That Sticks Before you even step inside, the property sets its own tone. Palm and fruit trees line the walkway, creating a path that feels both native to the landscape and distinctly curated. It's a subtle signal that this place is different. Once you're through the door, the scale hits you. A floating staircase anchors the main living area, and those 12-foot doors give the ground floor a genuinely grand feel. Engineered hardwood runs underfoot throughout, but the finishes stay quiet. They let the architecture and those endless bay views do the talking. ### Where the Living Happens The floor plan is wide open, flowing straight from the foyer to the bayside. The kitchen, dining room, and family room all share floor-to-ceiling retractable glass, so the line between indoor and outdoor living basically disappears. In the kitchen, minimalism rules. Quartz countertops, a full Miele and Thermador appliance package, and a hidden walk-in pantry keep the main space clean and clutter-free. It's the kind of kitchen that makes you want to cook, or at least pretend you do. ### The Primary Suite and Guest House Downstairs, the primary suite is designed for both comfort and accessibility. It offers full views of the 50-foot saltwater lap pool and the bay beyond. A large picture window floods the primary bath with natural light, and you'll find a standalone tub and dual sinks in there. A walk-in closet sits just across the hall. One of the smartest design choices? The primary suite shares an outdoor patio with a separate one-bedroom, one-bath guest house. That gives you a fully independent space for family, staff, or overflow guests without stealing any square footage from the main house. ### Upstairs Flexibility Head upstairs, and you'll find three additional ensuite bedrooms, two of which have balcony access. There's also a large bonus room that opens onto a turfed-lawn deck facing the bay. This is a flexible fourth space that can shift roles depending on who's staying. Home office, media room, extra lounge — it's up to you. ### Outdoor Living That Rivals Any Resort The outdoor patio is where modern-tropical design really shines. A sculptural gateway echoes the home's cantilevered architecture, and the amenities list reads like a resort brochure: - 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 ### For the Water Lovers If you've got a boat, you're in luck. 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 of the property, there's an oversized air-conditioned garage with EV charging and a half bath, plus a covered carport adjacent to the main house. ### The Bottom Line 19 Avacado Street isn't just another Islamorada estate. It's a rare combination of exceptional architecture, outstanding construction, and those famous Florida Keys sunsets. For more information or to schedule a showing, reach out to The Agency's Lisa Swanson.