by SC Feature Writer Reanna Haase
The bronze dolphin fountain statue centered in the expansive driveway of Dolphins Crossing is just the beginning of this rare Gulf-to-Bay Captiva estate. The historic property – anchored by a guest cottage once visited by Theodore Roosevelt and represented by Valerie Tutor of Kingfisher Real Estate – closed on July 23 in a $10 million sale, signaling a new chapter for the islands’ luxury real estate market.
Tutor worked with the previous owners to buy the home in 2019, and when they decided to move to The Sanctuary Golf Club, she was ready to help them get exactly what they were looking for in this sale.
“It’s one of the highlights of my career,” Tutor said. “I’m not a salesperson; I’m a realtor. I like to help people reach their goals, get what they want. Sometimes, you don’t pick the island – the island picks you.”
Some of the striking features of the three-story, 6,313-sq-ft main residence include four bedrooms and five bathrooms, simultaneous Gulf and Bay views through the floor-to-ceiling pocketing glass sliders in the living room, Viking appliances in the kitchen, a private elevator serving all three floors, and a private backyard oasis.
The home was originally built in 2005, but was almost entirely redone inside and out starting in 2019, when the previous homeowners undertook a full renovation shortly after they purchased the home.
“They are longtime partners, and when they got this house completely redone, they had their wedding there. It was just beautiful,” Tutor said. “This was a beautiful chapter in their lives together, and they’re a fantastic couple… So, to help them move to the next chapter of their lives and to continue helping them like that has been a privilege for me.”
On the bay side of the property sits a guest cottage, originally a boathouse, where former President Theodore Roosevelt anchored his houseboat off the dock, as part of his hunt for the giant manta ray. The former boathouse/guest cottage is named on the Lee County Historic Register.
Not only does its historic significance make this property stand out among other island properties, but its plot has earned it the title of one of only a small handful of Gulf-to-bay estates on Captiva – fewer than 20, according to Kingfisher records.
“There are only a few of those houses on the islands that are literally Gulf-to-Bay,” Tutor said. “That’s very rare, and it’s one little stretch where you can find those homes that are true Gulf-to-Bay.”
The buyers of this home are a couple with a primary residence in Virginia Beach, who have previously owned the islands and were looking to upsize to host their family, said Tutor. One of the main draws of their new Captiva home was its breathtaking water views.
“The buyers have gotten a great deal,” Tutor said. “It was definitely a capstone sale for me. I have been very blessed to have lots of great customers and clients.”
The previous owners bought Dolphins Crossing in 2019 for $6 million, and in a 2025 appraisal, the home was valued at $11 million, following the complete remodel. Even with such a substantial sale, the new owners have found an amazing deal in this historic estate.
“We feel very fortunate to have been able to assist with the sale of such an obviously prestigious property,” said Phaidra McDermott, Kingfisher Real Estate Broker/Owner. “We are so grateful and thankful to have been able to procure a buyer during a difficult time. The market has been challenging over the last several years, but we definitely anticipate a strengthening, and we’ve already experienced a strengthening.”
This sale is among many luxury sales the island real estate company has closed this year. McDermott shared that they have closed on two other notable properties in the first half of the year: 4257 West Gulf Dr for $9.5 million and another property on the ‘Tween Waters stretch sold at land value for $7.5 million.
“It’s about time for our area to start to procure higher values,” McDermott said. “I’m pleased to see this; it’s happened numerous times this past season.
Over the years, the islands have seen extreme fluctuations in the real estate market, from the surge of buyers drawn to Florida’s low interest rates during the COVID-19 pandemic, to the wave of new listings that followed the 2022 and 2024 hurricane seasons.
Now, after widespread rebuilding and remodeling in the wake of Hurricane Ian, the market is defined by new construction and fully reimagined properties, and high-end sales like Dolphins Crossing signal an uptick that many expect will mark the next chapter for the islands.
“Last March or February, I would say, all of a sudden, you really started to feel a change and a shift in momentum,” McDermott said. “What we anticipate is that as the islands reemerge, if you will, which they are by the level of remodeling, the amount of new construction, the reinvention – what’s going to happen is it’s going to change. It’s kind of a trickle-down effect.”
With this, the team at Kingfisher still maintains that sales like this don’t just come about. It takes special knowledge of the islands, the home, and a passion for the sale.
“How special that Valerie was the one to represent the home, because she’s been a part of the islands since the 1960s,” McDermott said. “Having that historical knowledge and tenure here for such a long time, I think, is important and reflects upon her successes.”
The big sales, like Dolphins Crossing, are among the most exciting at Kingfisher, but Tutor said this is just part of what she does. All sales are the same to her; her passion for the islands and helping others is what stays consistent through every closing.
“I don’t care if it’s a $100,000 property or a $10 million property. I treat everyone the same,” Tutor said. “It’s still somebody’s property, somebody’s house, or it’s going to be somebody’s house. I really love making that happen for whomever that person is.”
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