For 50 years, Harbor Towers Yacht & Racquet Club, 5855 Midnight Pass Road, has stood like a sentinel, watching over Siesta Key.

As owners celebrate the condo’s 50th anniversary, they are reflecting on its past.

The building can trace its beginnings to the early 1970s. The Harbor Towers Owners Association was incorporated Oct. 5, 1972, and groundbreaking likely took place in 1974.

The property received its certificate of occupancy Oct. 30, 1975, and was completed in 1976. The seven-story, Y-shaped building contained 211 residences, with amenities including a private marina, three lighted tennis courts, swimming pools, separate exercise rooms with saunas for men and women, and landscaped grounds.

Some of those amenities have evolved over the decades. The original separate exercise areas were eventually replaced by a single fitness center, while the marina, pools and tennis courts remain. The award-winning landscaped grounds today include a waterfall and pond, with Harbor Towers describing the waterfall as a “Siesta Key landmark.”

John Quinn, 95, has watched Harbor Towers evolve almost from its beginning, but his connection to Siesta Key reaches back even further. While stationed at MacDill Air Force Base from 1953 to 1956, Quinn visited Siesta Key and later recommended the island to his father. His parents moved there in 1969, and after renting for a time, his father moved into nearby Whispering Sands in 1971, where he served as condo association president. Quinn watched Harbor Towers being constructed during those years. “I watched it go up,” he recalled.

He purchased his own unit in July 1987 and became deeply involved in the property, including longtime service on the building committee. Quinn said he helped oversee projects including carports, awnings, gazebos and major work on the building, roof and marina. The marina was rebuilt in phases over several years, with the work funded through reserves rather than a special assessment.

Quinn has also watched Siesta Key itself change dramatically, particularly as traffic increased across the area. He recalled a time when getting on and off the island was far less of an undertaking.

“He used to drive every day to lunch from here over to St. Armands for a hamburger, at least five days a week,” Quinn said of his father.

Social life at Harbor Towers was lively as well. Quinn recalled big bands performing in the lobby several times a year. “Oh yeah, we danced, wore a coat and tie,” he said.

That tradition of resident involvement has continued as Harbor Towers has aged, with owners taking an active role in maintaining and improving the property. In recent years, that commitment would be put to perhaps its greatest test yet.

When the 2024 hurricanes Helene and Milton struck, Harbor Towers became the proverbial harbor in the storm.

Association President Pat Palumbo said Harbor Towers had just completed the largest renovation project in its history. Beginning in 2021, the association hired a structural engineer to assess the nearly 50-year-old building and ultimately undertook a roughly $13 million project that Palumbo described as essentially rebuilding it “from the inside out.”

The work included replacement of the building’s glass to updated hurricane specifications, reconstruction of exterior walls, reinforcement of wall studs and extensive waterproofing. Palumbo said the reinforcements were designed to withstand winds exceeding 200 mph. The most amazing part of all: the project was completed about a month before Hurricane Milton made landfall on Siesta Key.

“We were tested almost immediately with a Category Three direct-hit hurricane and came through with flying colors,” Palumbo said.

Despite wind gusts measured at about 130 mph on the roof during Milton, Palumbo said the renovated building envelope sustained no damage. Carports, pools, landscaping and other areas of the property were affected, and the roof, which was not part of the renovation project, sustained some damage and has since been replaced.

A handful of residents remained in the building despite evacuation orders. Palumbo said he urged them to leave, but they told him they “felt safer there than anywhere else.” After the storm, Harbor Towers also housed people displaced by damage elsewhere, along with crews working on cleanup and restoration.

The marina also weathered the storms remarkably well. Palumbo estimated storm surge there reached nearly 7 feet. One boat broke loose but remained in the marina, while all the others stayed secured in their slips.

The renovation required assessments ranging from the low $40,000s to nearly $100,000, depending on unit size, and Palumbo said the project initially faced resistance, with some selling in lieu of the additional costs. After the hurricanes, however, he said most owners were grateful the work had been done.

For owner Dave Lovell, who bought at Harbor Towers with his wife, Carol, in 2020, the renovation demonstrated the willingness of residents to invest in the property’s future. Lovell, who has served on the building, marina and rental committees, said he was proud of the community’s commitment to keeping Harbor Towers thriving. That involvement extends beyond maintenance and improvements. Lovell described Harbor Towers as a community of year-round residents, seasonal owners and vacationers, with social events that welcome them all.

“I think it’s very community oriented,” he said, adding that “everybody is just very, very welcoming.”

Fifty years after Harbor Towers first rose over Siesta Key, much around it has changed. The island Quinn remembers — where his father could routinely make the trip to St. Armands for a hamburger — is decidedly different. Harbor Towers has changed, too, through renovations, hurricanes and generations of owners.

But the commitment to the building and the community within it has endured.

“There is a solid core group on a lot of these committees that truly care about the property,” Lovell said. “And that shows.”