Some homes remain frozen in time.
This one kept evolving.
A former HGTV Dream Home, first introduced to television audiences in 2008, has returned to the spotlight after an extraordinary transformation.
Now listed for $14.9 million, the waterfront estate at 139 Gimpy Gulch Drive in Islamorada bears little resemblance to the property viewers first admired nearly two decades ago.
Represented by Brett Newman of Coldwell Banker Schmitt Real Estate Co., the estate has grown from a single showcase residence into a 3.2-acre bayfront compound with multiple homes, resort-style amenities, and one of the most impressive turnkey packages currently available in the Florida Keys.
From television dream to private compound
When HGTV selected the property as its 2008 Dream Home, the estate consisted solely of what is now the central residence.
Since then, it has expanded dramatically.
Today the property encompasses three separate buildings, a sprawling resort-style pool, a new deep-water dock, extensive outdoor entertaining spaces, and additional acreage that has transformed the once-famous television home into a true waterfront compound.
Despite its expansion, the estate still embraces the laid-back architectural style that made the original home so memorable, drawing inspiration from classic Florida Keys design with inviting indoor-outdoor living spaces at every turn.
Three buildings create a flexible family retreat
The compound offers approximately 6,573 square feet of living space spread across three distinct structures.
The main residences include a two-bedroom, two-and-a-half-bath home with convenient ground-floor living and a larger tri-level residence featuring three bedrooms and three-and-a-half baths.
Completing the ensemble is a separate media house with its own bedroom, one-and-a-half bathrooms, and an attached two-car garage, providing flexible accommodations for guests, extended family, or staff.
Altogether, the property includes six bedrooms and nine bathrooms.
The original Dream Home remains the centerpiece
Although the estate has expanded dramatically since its HGTV debut, the original Dream Home continues to anchor the compound.
Designed with the easygoing character of the Florida Keys in mind, the residence is filled with light, breezes, and inviting gathering spaces that flow naturally from one room to the next.
Large windows and generous outdoor connections ensure the surrounding water remains a constant presence throughout the home.
Coastal kitchens with a European twist
The kitchens strike a balance between relaxed island living and serious culinary capability.
Premium Sub-Zero refrigeration is paired with coveted La Cornue cooking appliances, giving both residences the kind of equipment more commonly found in professionally designed chef’s kitchens.
Whether preparing a quiet family dinner or catering a celebration, the spaces were designed to perform while remaining warm and welcoming.
Resort living centered around the pool
At the heart of the estate sits an extraordinary 100-foot swimming pool that stretches dramatically across the grounds.
An oversized spa anchors one end, while expansive terraces, shaded seating areas, and a covered outdoor kitchen with bar create an atmosphere reminiscent of a boutique island resort rather than a private residence.
Whether hosting large gatherings or enjoying a quiet afternoon overlooking the bay, the outdoor spaces were clearly designed to be the centerpiece of daily life.
More than 250 feet of private bayfront
Privacy is one of the estate’s defining luxuries.
Hidden behind mature tropical landscaping and accessed through private gates, the property stretches across more than 250 feet of sandy shoreline overlooking Florida Bay.
The setting combines spectacular sunset views with direct boating access, allowing owners to reach both Florida Bay and the Atlantic Ocean via nearby Snake Creek within minutes.
For boating enthusiasts, it’s difficult to imagine arriving better prepared.
A dock that comes fully stocked
The newly built deep-water dock is only the beginning.
Included in the sale is an impressive collection of recreational equipment valued at more than half a million dollars, turning the property into an instant waterfront playground.
The package includes a 34-foot EdgeWater boat powered by twin 400-horsepower Yamaha engines, a pair of WaveRunners, a UTV tow vehicle, kayaks, paddleboards, bicycles, fishing gear, and other equipment — allowing the next owner to begin exploring the Keys from day one.
Valuable development potential remains
Even after its significant expansion, the estate still offers room for future possibilities.
The sale includes an adjacent vacant parcel along with valuable development rights estimated to be worth approximately $1.2 million — a particularly significant asset in the tightly regulated Florida Keys, where opportunities for new development have become increasingly limited.
Combined with roughly two acres of upland and an additional 1.2 acres of bay bottom, the property offers both exceptional privacy and long-term flexibility.
Steps from one of Islamorada’s favorite parks
Although the estate feels wonderfully secluded, everyday conveniences remain close at hand.
Just a short walk away, Founders Park offers tennis and pickleball courts, sports fields, festivals, playgrounds, waterfront recreation, and community events throughout the year, adding another layer of appeal for families and seasonal residents alike.
A rare second act
Former HGTV Dream Homes don’t land on the market very often.
Former HGTV Dream Homes that have evolved into fully realized waterfront compounds are even rarer.
What began as a nationally televised showcase residence has matured into one of Islamorada’s most distinctive private estates — combining resort amenities, exceptional boating access, and a level of turnkey convenience that’s almost unheard of in the Florida Keys.
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