$29 Million Villa Lago Is One of the Florida Keys’ Most Extraordinary Waterfront Estates

Known as Villa Lago, this extraordinary Islamorada estate blends authentic Italian craftsmanship with 220 feet of Florida Bay frontage, a private white-sand beach, and one of the most architecturally distinctive waterfront homes ever offered in the Florida Keys.

Few waterfront homes in the Florida Keys aspire to become architectural landmarks.

Villa Lago does exactly that.

Positioned on approximately 220 feet of pristine Florida Bay shoreline in Islamorada, the Italian-inspired estate is unlike anything typically found in the Keys. Rather than embracing contemporary coastal minimalism, the residence transports owners to the villas of Tuscany and Florence through authentic European craftsmanship, imported materials, and extraordinary attention to architectural detail—all while overlooking some of the clearest waters in North America.

Now offered for $29 million, Villa Lago encompasses more than 8,100 square feet of living space on a secluded one-acre bayfront property, pairing Old World artistry with the effortless waterfront lifestyle that has made Islamorada one of Florida’s most coveted luxury destinations.

“Villa Lago is one of those properties that simply cannot be compared to anything else in the Keys,” said Leslie Leopold of Ocean Sotheby’s International Realty. “It’s an authentic Italian villa placed on one of the most spectacular waterfront settings in Florida.”

A European Villa Hidden in the Florida Keys

The arrival immediately sets Villa Lago apart.

Passing through private gates, visitors enter a residence where 30-foot ceilings, dramatic proportions, and handcrafted architectural elements create an atmosphere more reminiscent of an Italian palazzo than a tropical waterfront home.

A remarkable arcaded hallway capped by a hand-tiled barrel-vaulted ceiling guides visitors through the residence, introducing an extraordinary collection of imported materials and artisan craftsmanship.

Hand-painted ceiling frescoes, carved marble corbels, Florentine quatrefoil windows, wrought-iron balconies, copper rain gutters, and a custom-imported Italian tile roof establish an architectural authenticity rarely achieved outside Europe.

“This wasn’t designed to imitate an Italian villa,” Leopold explained. “It was created using the same level of craftsmanship and artistic detail you would expect to find in Italy itself.”

Every Room Framed by Florida Bay

While the architecture recalls Europe, the views remain unmistakably Florida.

Expansive living spaces overlook the turquoise waters of Florida Bay, creating a dramatic contrast between timeless Italian interiors and the tropical landscape beyond.

Natural light floods the residence throughout the day, while carefully positioned balconies and terraces strengthen the relationship between the home and its extraordinary waterfront setting.

Five fireplaces distributed throughout the estate reinforce its warm residential character despite its impressive scale.

A Kitchen Built for Entertaining

Luxury entertaining begins in the heart of the home.

The chef’s kitchen combines professional performance with elegant design, featuring premium Viking, Sub-Zero, Miele, and U-Line appliances together with a spacious walk-in pantry and dedicated preparation kitchen.

A pass-through serving window connects directly to the outdoor entertaining pavilion, where a second kitchen equipped with a Viking grill, refrigeration, ice maker, bar seating, and covered dining area overlooks the swimming pool and bay.

“The indoor and outdoor kitchens work together beautifully,” Leopold said. “It’s an ideal setup for waterfront entertaining.”

A Primary Suite Occupying an Entire Floor

Unlike conventional luxury homes, Villa Lago dedicates its entire third floor to the owner’s private retreat.

The suite combines remarkable scale with intimate living spaces, including a private office, tea room, sitting room, custom dressing room, dedicated laundry, and multiple balconies overlooking both the great room and Florida Bay.

Two fireplaces add warmth throughout the suite, while the spa-inspired primary bathroom transforms daily routines into a resort experience.

Every aspect of the retreat has been designed to create complete separation from the guest accommodations located on the main level.

A Home Built Around Leisure

Beyond its architectural beauty, Villa Lago offers an exceptional collection of lifestyle amenities.

A richly detailed billiards lounge features mahogany coffered ceilings and rare coconut wood flooring, while a private theater complete with wet bar provides an immersive entertainment experience.

A dedicated wellness room and private sauna further enhance the home’s emphasis on relaxation and well-being.

Throughout the residence, luxury is expressed not through excess but through thoughtful experiences.

Resort Living on the Water

The outdoor environment rivals many of the world’s finest boutique resorts.

An elegant infinity-edge swimming pool flows toward Florida Bay, complemented by a distinctive sunken gazebo with integrated swim-up seating.

Professionally landscaped tropical gardens surround fountains, entertaining terraces, and a private putting green, while a white-sand beach creates effortless access to the crystal-clear waters beyond.

For boating enthusiasts, the estate’s deep-water dockage provides immediate access to some of the world’s finest offshore fishing, diving, snorkeling, and cruising destinations.

An air-conditioned boat room and dedicated skiff ramp further distinguish the property from traditional waterfront homes.

“This estate was designed to celebrate life on the water,” said Annie Hagen of Ocean Sotheby’s International Realty. “Every outdoor space connects naturally to Florida Bay.”

Modern Technology Behind Timeless Design

Although inspired by centuries-old European architecture, Villa Lago incorporates the infrastructure expected of a contemporary luxury residence.

A private elevator services all three floors, while Control4 automation and Sonos audio integrate lighting, entertainment, and comfort throughout the estate.

A remarkable 4,000-square-foot climate-controlled collector’s garage accommodates extensive vehicle collections while maintaining the same architectural standards found throughout the residence.

Secure perimeter walls and private gates complete the property’s comprehensive approach to luxury living.

One of Islamorada’s Most Distinctive Waterfront Estates

Luxury inventory throughout the Florida Keys remains exceptionally limited, particularly for architecturally significant waterfront compounds.

Villa Lago distinguishes itself not only through its exceptional location, but through its commitment to authentic European craftsmanship—a combination virtually impossible to duplicate today.

According to Leopold, Villa Lago represents something increasingly uncommon.

“It’s a home that offers two extraordinary lifestyles at once—the romance of an authentic Italian villa and the unparalleled boating, fishing, and waterfront living that only Islamorada can provide.”

Prospective buyers can also explore additional photography, floor plans, pricing history, and current availability on Zillow.

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Property Overview

• Address: 75090 Overseas Highway, Islamorada, Florida 33036
• Property Name: Villa Lago
• Price: $29,000,000
• Bedrooms: 4
• Bathrooms: 6
• Living Area: 8,194 square feet
• Lot Size: Approximately 1 acre
• Year Built: 2011
• Highlights: 220 feet of Florida Bay frontage, private white-sand beach, two-story boat dock, infinity-edge pool, sunken swim-up gazebo, 4,000+ square-foot collector’s garage, elevator, private theater, billiards lounge, wellness room, authentic Italian craftsmanship.

Listing Representation

The property is represented by Leslie Leopold and Annie Hagen of Ocean Sotheby’s International Realty.
For additional information or to arrange a private showing, interested buyers may contact Leslie Leopold at (305) 942-0215 or Annie Hagen at (305) 304-1762.