HGTV’s 2008 Dream Home Returns to the Market—as Part of $15 Million Private Islamorada Resort With 100-Foot Pool

A former HGTV Dream Home in the Florida Keys has been transformed into an astonishing waterfront compound and placed back on the market for $14.9 million—nearly double the price it was last sold for in 2021.

The property, which is located in Islamorada, began as a single dwelling that was overhauled by HGTV experts and then unveiled as the Dream Home in 2008, when it was won by Iowa couple Stephanie and Tommy Dee.

At the time, the house was valued at around $2.2 million. However, the winners opted not to keep the dwelling, instead choosing a cash prize. Soon after, the home was placed on the market and sold for $2 million.

It has since changed hands on just a few occasions, in 2009 and then again in 2021, when it was sold for $8 million to a buyer who has now transformed the property into what listing agent Brett Newman with the Newman Team at Coldwell Banker Schmitt Real Estate Co. describes as a kind of private resort.

“It started out years ago, in 2008, as the HGTV Dream Home Giveaway, and it has evolved since then,” Newman explains. “Space is at a premium here in the Keys, and this is like having literally your very own resort to hang out.”

The 3.2-acre property in Islamorada now includes three structures, with the center one being the 2008 HGTV Dream Home. Linda Woodrum designed the approximately 3,200-square-foot home back then, and it hasn’t been changed much since.

“It's like a time capsule. It's exactly the same decor. You could lay the pictures over one another, and it would be the same,” Newman says. “All of the owners have decided to keep it that way, and everyone has improved" the property.

Now used as a guesthouse, this three-story home has three bedrooms and three bathrooms and was designed with a bright blue and yellow palate to blend with the surroundings.

On one side of the HGTV house is what the sellers call the main house, a two-bedroom, two-bathroom home, which was built in 2014 and updated within the past five years.

“They just made it very comfortable for themselves. They did an amazing kitchen and an amazing bathroom that opens out into the garden with the bathtub out in the garden.”

A third structure, what the sellers call the media house, is on the other side of the former dream home and has a two-car garage with a bedroom, bathroom, and kitchenette.

All three structures look out on to the expansive backyard with its huge 100-foot pool.

“I've never seen a pool like that on any residential property. It's probably one of the largest ones in the Keys if I had to take a guess,” Newman says, with “a giant hot tub you could probably fit 10 people in easily.”

The nearby cabana has all kinds of little extra touches.

“They were hot outside, so they put air conditioning in the pool cabana. It has a nicer kitchen than a lot of high-end houses,” he says, adding it’s the kind of place you see at a resort. “You expect to see a bartender sitting behind the cabana.”

Then there’s the 250 feet of sandy beach on the bay near a deep-water dock, where the sellers kept some of their water toys, all of which convey with the house.

“It comes with so many extras, it's ridiculous. It comes with a $400,000 boat, two Jet Skis, a little 4-by-4 to move them, all of the furniture, all of his fishing gear, electronics, kayaks, stand-up paddles,” Newman says. “You bring your toothbrush, but I'm sure one could be arranged for you if you wanted.”

Newman says the seller has put in beautiful landscaping, including trees which help provide privacy to the compound.

“You could charge an admission to just walk through the property,” he says. “The weather and heat are pretty tough on plants here, but every single thing is green and in bloom, from fruit trees to amazing tropical flower trees, banana trees, you name it.”

In addition to the homes and the land, the sale includes three development rights permits, which are coveted in the Keys.

“Here in Islamorada, there are no more building rights. So, if you were just someone who owned a vacant lot and said, 'Oh, when I retire, I'm building a house in the Keys.' No, you're not because there are no more building rights left,” he explains. The additional building rights could be sold for no less than $400,000 each.

An additional nearby lot is also available for sale, which includes another building rights attachment as well as access to a boat ramp and boat basin, making an already large compound even bigger.

“It could be so much. It could be a family compound. It could be a corporate retreat. It could be monthly rentals,” he says.

The property would also be good for a celebrity, he notes. “You could come and go pretty easily.”

An adjacent city park comes with a dog park, pickleball courts, pool, tennis court, golf range, and more.

Newman says usually properties are missing something buyers want, but not this one.

“We've been selling real estate here forever, and we get to see a lot of nice stuff. There's always some sort of give and take on something, and this ... property literally has it all.”

And it’s all ready to go.

“You could walk the place with a white glove and a magnifying glass, and I would dare you to find anything wrong with it,” he explains.

The property comes to the market at a very exciting time for Islamorada, which was recently thrust into the headlines when Barstool Sports founder Dave Portnoy purchased a mansion in the coastal village for a record-breaking $27.8 million in October 2025.

Since then, interest in the enclave has surged, local listing agent Lisa Swanson of The Agency Florida Keys previously revealed to Realtor.com®.

"Dave Portnoy definitely helped put Islamorada on the market," Swanson said. "There has been a lot of interest in the area since then, especially for buyers looking for turnkey luxury."

According to the agent, sales in Islamorada have shot up by about 20% since Portnoy's home purchase.

"There are a lot of trophy properties here, and we certainly get more interest from both buyers and sellers when we mention Dave Portnoy's home," she noted.