LIFE BEYOND FIRST CLASS
ESTATES
A WORLD OF ITS OWN
Spanning more than 8,000 square feet on one acre with 220 feet of Florida Bay frontage, Villa Lago is a private Islamorada
compound of monumental scale, Old World craftsmanship, deep-water access, and resort-level seclusion.
75090 Overseas Highway, Islamorada, Florida
$29,000,000
REBECCA ETORIA
Villa Lago does not present itself as a conventional waterfront residence. It arrives as a fully realized private compound, vast in scale, exacting in craftsmanship, and positioned along 220 feet of Florida Bay with the confidence of an estate intended to endure.
Set behind gates on one acre, the Italian-inspired residence spans 8,194 square feet and brings together the grandeur of a palazzo with the infrastructure of a serious Florida Keys retreat. Deep-water dockage, a private white-sand beach, an infinity-edge pool, extensive entertaining grounds, and a collector’s garage exceeding 4,000 square feet create a property that is not simply impressive in parts. It is complete.
That completeness is its greatest luxury. Few estates can offer this degree of architectural detail, boating access, privacy, recreation, and accommodation within a single walled setting. Villa Lago was not conceived to participate quietly in the Islamorada market. It was created to stand apart from it.
The first impression is unapologetically grand. An imported tile roof, Florentine quatrefoil windows, marble corbels, wrought-iron balconies, and copper rain gutters establish the language of an Old World villa before the interiors are revealed. Fountains, palms, formal landscaping, and the blue expanse of Florida Bay complete an arrival that feels transported from the Mediterranean, yet inseparable from the tropics.
Inside, ceilings rise approximately 30 feet above a grand living space framed by turquoise water views. An arcaded gallery extends through the residence beneath a hand-tiled barrel-vaulted ceiling, creating a sense of procession rarely found in contemporary island architecture. Every turn reveals another layer of craftsmanship, from detailed marblework and Italian finishes to hand-painted frescoes and five fireplaces.
These are not decorative gestures applied to a standard coastal home. They are foundational to the estate’s identity. Villa Lago feels commissioned rather than assembled, with architecture, art, and craftsmanship working together to create rooms of genuine consequence.
The formal dining room is crowned by a painted ceiling fresco, setting the stage for dinners that call for ceremony rather than speed. The adjoining chef ’s kitchen is equipped with Viking, Miele, U-Line, and Sub-Zero appliances, supported by a walk-in pantry and separate preparation kitchen. A pass-through connects directly to the outdoor kitchen, where bar seating, refrigeration, an ice maker, and covered dining allow entertaining to move effortlessly toward the bay.
The home offers four bedrooms and six bathrooms, but the numbers reveal little about the generosity of the plan. Three guest suites are positioned on the main level, each providing privacy within the larger estate. The entire third floor is reserved for the primary retreat, transforming it into a private residence of its own.
Two fireplaces, an office, tea room, sitting room, custom dressing room, private laundry, spa-inspired bathroom, and multiple balconies compose a suite designed for long stays rather than hurried escapes. From above, the owners can look across the interiors, gardens, and bay, enjoying separation from the household without ever feeling removed from the landscape.
An elevator connects all three levels, making the estate’s scale effortless. Elsewhere, a private theater with a wet bar, billiards lounge, wellness room, and sauna create distinct destinations within the home. Mahogany-coffered ceilings and coconut wood flooring reinforce the sense that each room was given its own architectural identity rather than treated as another space to fill.
Yet Villa Lago is at its most extraordinary where the architecture meets the bay.
The infinity-edge pool appears to dissolve into Florida Bay, extending the sightline beyond the estate and toward the horizon. A sunken gazebo with swim-up seating creates a place for afternoons to unfold without interruption, while fountains, terraces, a putting green, covered lounges, and tropical gardens turn the grounds into a private resort reserved for a single household.
The white-sand beach creates a softer threshold to the water, an uncommon luxury among substantial bayfront estates. It allows the property to move between formality and ease, from frescoed dining rooms and marble galleries to bare feet at the water’s edge.
For the serious yachtsman, the estate’s beauty is matched by capability. Its 220 feet of Florida Bay frontage incorporates deep-water dockage, a private skiff ramp, and an air-conditioned boat room. Offshore fishing, flats excursions, diving, snorkeling, and passage toward the Atlantic can begin directly from the property, without dependence on a separate marina.
That immediacy matters in Islamorada, where ownership is often measured by access to the water. Known internationally for sportfishing, the village occupies a coveted position between Florida Bay and the Atlantic, placing backcountry waters, coral reefs, and offshore fishing grounds within reach. Life here is guided by tides, weather, and the possibility of leaving by boat with little notice.
Villa Lago is designed for an owner whose collections extend beyond the water. A garage of more than 4,000 square feet provides substantial space for automobiles, recreational vehicles, boating equipment, and the machinery required to support an estate of this magnitude. It is infrastructure concealed within architecture, allowing the property to function at a level equal to its presentation.
Control4 smart-home technology, integrated Sonos audio, impact-resistant glass, secure walls, and a generator place contemporary capability discreetly behind the residence’s classical detailing. The result is an estate that appears timeless without asking its owner to compromise on modern performance.
Beyond the gates, Islamorada offers a form of luxury defined less by spectacle than access. The Village of Islands stretches through the Upper Keys, surrounded by water and shaped by a longstanding culture of fishing, diving, boating, and conservation. Its small scale and limited development have helped preserve a sense of separation from the mainland, even as private aviation, marinas, resorts, galleries, and notable restaurants serve a sophisticated international audience.
Fine dining retains the island’s connection to the water. Pierre’s at Morada Bay pairs polished service and refined coastal cuisine with one of Islamorada’s most romantic bayfront settings, while newer concepts such as Kindler bring elevated, wood-fired cooking to the Keys. The experience remains unmistakably local, with sunsets, fresh seafood, and the water maintaining as much presence as the menu.
The area’s history adds depth to its beauty. Islamorada was once connected to Henry Flagler’s Overseas Railway and later endured the devastating Labor Day Hurricane of 1935, events that helped shape the resilience and identity of the Upper Keys. Over time, it became synonymous with sportfishing, attracting figures such as Ted Williams and generations of anglers drawn to its surrounding waters.
Villa Lago belongs to that landscape, but it does not resemble anything conventionally associated with it. Its architecture looks toward Italy, its scale rivals that of a private resort, and its boating infrastructure is unmistakably rooted in the Keys. The tension between those worlds is precisely what makes the property so compelling.
A discerning buyer can commission another large home. Materials can be sourced, technologies upgraded, and interiors recreated. What cannot be easily reproduced is the complete composition found here: one acre on Florida Bay, 220 feet of frontage, deep-water access, a private beach, monumental interiors, collected craftsmanship, extensive recreation, and the capacity to house automobiles and vessels within one secure estate.
Villa Lago is not simply a place from which to enjoy Islamorada. It is a world unto itself, created for an owner who understands that true rarity is found not in any single amenity, but in the near-impossible convergence of land, water, architecture, craftsmanship, and scale.
75090 Overseas Highway, Islamorada is offered at $29,000,000.
For more information or to schedule a private viewing, please contact:
Anne Hagen
Real Estate Advisor
T: +1 305.304.1762
T: +1 305.712.8888
E: ahagen@oceansir.com
Leslie Leopold
Real Estate Advisor
T: +1 305.942.0215
T: +1 305.712.8888
E: lleopold@oceansir.com
W: https://75090-overseas-highway.oceansir.com/
Join our mailing list to receive curated updates, special features, and invitations to events that define the world of the discerning few.
Sign up today and never miss what’s next.