Custom-designed by renowned Charles Vincent George Architects, the waterfront estate at 19 Avacado Street is a standout departure from the beachside bungalows more common in Islamorada. The 5,489-square-foot poured concrete estate reads more coastal Modernism, with panoramic sunset-facing bay views through floor-to-ceiling continuous glass windows—offering a unique combination of contemporary design paired with the renowned seaside lifestyle of the Florida Keys. Located at one of Islamorada’s premier and most sought-after bayfront streets, the property, represented by The Agency’s Lisa Swanson, encompasses 1.27 private acres covering a two-parcel lot.

Palm and fruit trees line a walkway that feels both native to the landscape and distinct from it, setting the tone before you reach the door. Inside, a floating staircase anchors the main living area, 12-foot doors lend the ground floor a grand sense of scale, and engineered hardwood runs underfoot throughout. The finishes stay quiet, allowing the architecture and views take the lead.

An open floor plan carries straight from the foyer to the bayside, where the kitchen, dining room, and family room all share floor-to-ceiling retractable glass and unobstructed water views. The minimalist kitchen is built around quartz countertops and a full Miele and Thermador appliance package, with a hidden walk-in pantry tucked out of sight to keep the main cooking space clear of clutter.

A first-floor primary suite offers comfort and accessibility, with full views of the sparkling 50-foot saltwater lap pool and bay beyond. A large picture window brings natural light into the expansive primary bath, outfitted with a standalone tub and dual sinks. A large walk-in closet is just across the hall.

The primary suite shares an outdoor patio with a separate 1-bedroom, 1-bath guest house, giving the property a fully separate space for family, staff, or overflow guests without borrowing square footage from the main house.

Upstairs, three additional private ensuite bedrooms (two with balcony access), and a large bonus room open onto a turfed-lawn deck facing the bay—a flexible fourth space that can shift roles depending on who’s staying.

The outdoor patio presents modern-tropical design to deliver resort-caliber relaxation, with a sculptural gateway that echoes the home’s cantilevered architecture.

Outdoor amenities include an elevated heated and chilled saltwater lap pool, private sandy beach area, entertaining terraces, mature tropical fruit trees, an air-conditioned garden shed, and a gated entrance ensuring 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 is an oversized air-conditioned garage with EV charging and a half bath. A covered carport is adjacent to the main house.

19 Avacado Street offers a distinctive opportunity to acquire one of the Florida Keys’ premier contemporary bayfront estates, combining exceptional architecture, outstanding construction, and spectacular sunsets. For more information or to schedule a showing, contact The Agency’s Lisa Swanson.