A lot has changed in Gillespie Park recently, as historic cottages and Mediterranean-style homes have been replaced with slick modern builds. The eclectic area is even seeing plans for million-dollar condos to join the neighborhood just north of downtown.

Despite it all—and almost 90 years later since they were built—Gillespie Park's iconic boat and lighthouse homes still stand as quirky and cute as ever. Less than a mile from the bayfront, they tell the story of Sarasota’s water-loving legacy.

In 1933, boatbuilder Oliver Blackburn—a pioneering Sarasota merchant and politician who was George Blackburn's brother—built the boat house, with its lapstrake hull (a method of boat building where the edges of hull planks overlap), for Arthur Rowe, who was a boat captain for John Ringling in the 1910s and then a captain for oil magnate William Selby (Marie Selby's husband) until World War II. Rowe retired to live in the boat and lighthouse in 1949. His son, Arthur Rowe Jr., moved there in 1959 to care for his father and remained there until 1984. 

It's said that Rowe wanted to live on a houseboat, but his wife wanted a real house. A house shaped like a boat but on land, with a lighthouse at its hull, was the compromise. 

It's also said that history repeats itself, and current boat tenants Kevin and Gillian Hagerty share the same conundrum and solution that Rowe had. Kevin Hagerty, 48, is also a water-loving captain who would prefer living on a boat to living on land. Gillian, 33, not so much.

“We were renting on Vamo Road, and Gillian sent the listing to me as a joke. But I called the number and that night we put a deposit on it," Kevin recalls. It marries well with their business: the couple owns a local charter called Southern Latitude Charters. They’ve lived in the home for two years now and say “It’s a blast” despite some “furniture challenges” due to the unusual interior lines. The boat captain theme is a given, and guests were required to wear a captain's hat at their housewarming. 

Although there's plenty of privacy thanks to lush trees and empty lots on either side, the house does have its paparazzi moments.

“The first day, we were unpacking and the trolley stopped in front of the house. We could hear people talking and taking pictures. I was shocked to find out we're a stop," Kevin says. "We have nightly Segway tour visits, too. We're proud."

The boat and lighthouse sit on one parcel, at 433 N. Osprey Ave., and can be purchased on their own. But two empty lots, one on each side, plus a wood-framed two-bedroom, one-bathroom cottage built in 1926 on the corner of N. Osprey Avenue and Fourth Avenue, just south of the iconic homes, can be included in the total purchase.

With vacant land becoming more scarce this close to downtown, developers may see big opportunities here, especially with zoning that allows for a mixture of uses. Residential dwellings can be single- or multi-family, up to a maximum of 12 units per acre. Additional dwelling units, on top of a main home structure on each lot, are also permitted. Low-intensity office and retail uses are also allowed, with retail space options for corner lots. Building height can reach up to three stories. The boat and lighthouse property is historically designated by the City of Sarasota, but designations have been overcome before.

Still, as financially sound as it may be for a developer, razing the boat and lighthouse to build bigger and higher will probably earn them local villain status.

It's something owner Josh Weiner and his father, Bruce, who bought the whole parcel for $725,000 in 2017, knew instinctively.

“We’re sensitive to the character of the parcel. We couldn't bring ourselves to touch it. It felt perfect the way it is. Every time we wanted to maybe add something, we decided not to, and let it be with great tenants," Josh says.

In 2017, Josh says, "My dad went to see it and said it was the coolest property and quintessential Sarasota and purchased it. The tree canopy and quirky buildings with a tie to Sarasota's past make it feel nostalgic."

They did little to the lighthouse and boat, although the previous owner, who bought it in 1993, had put about $70,000 into repairs and a new concrete foundation for the boat, which once sat on palm logs. Before tenants like the Hagertys, the two structures were used as short-term vacation rentals, quenching the thirst for travelers in search of unusual spaces.

Its previous tenants were interesting, too. "The man living in the lighthouse when we bought it had a lighthouse tattoo to honor it," Josh says.

Weiner and his father lead the Longboat Key Group, a development, investment and property management firm that spearheaded the nearby CitySide Apartments, also in 2017, in the now-coveted Rosemary District. At the time, they took a risk on the neighborhood, which once held some of the lowest home values in town and was often known as "the wrong side of Fruitville Road." But as one of the first new apartment buildings in the neighborhood, CitySide filled up fast with the young working professionals the area is known for—including Josh himself for a few years, before having kids begged for single-family home living.

Before settling in Sarasota seven years ago, he lived in Seattle and Shanghai. Josh's family has invested in the area because “this place is dynamic and there's an energy here that likens to those cities," he says. He's only adding to that energy with Parkside, an "almost-outdoor food court" project headed to 1371 Boulevard of the Arts, next to the future pocket park in the heart of the Rosemary District, just west of Gillespie Park and the boat and lighthouse.

"The goal is homegrown concepts and a community gathering space—no chains.  Really, it's selfish, because our family wants to hang out here," he says.

The two vacant lots, the boat and lighthouse and the cottage can be purchased separately or all together to make up the entire block between Fourth and Fifth Streets on N. Osprey Avenue. The cottage is $699,900, the lots are each $399,900 and the boat and lighthouse are $949,000.

Interested? Call David Crawford of Catalist Realty at (386) 871-4600.