Made in Tampa: Windstar Homes

By McKenna Kelley

From the moment you pass through the pivot front door of Club Mez, one of Windstar Homes’ newest custom houses, company principal and co-owner David Lesser is beaming.

He’s eager to point out each of the home’s subtle, almost subliminal details.

See how the windows in each room line up with each other? And how the stainless steel and matte black of the farmhouse sink match that of the range hood? His partner and co-owner Bobby Gross is a bit more reserved, but get him talking too, and it becomes clear: These guys are obsessed with building homes.

“When we were in college, Bobby always said, dude, you’re going to build my dream house,” Lesser says. “What he didn’t know was he was going to be building it with me.”

Today, all Windstar Homes does is build dream houses. The company specializes in custom homes ranging in size from 3,000 square feet to over 30,000 square feet, forgoing commercial and remodel projects to commit to the cutting edge of new home construction. In the process, the University of South Florida classmates have made Windstar one of the leading builders in the southeastern United States.

“I remember the first project that we did together, the sheer joy we had,” Gross says. “[We were] a couple of young kids who really, back then, didn’t care about the money. We didn’t care about the accolades. We just cared about the joy of the work and the quality of the work and the pursuit of perfection of the work. We figured if we really honed our skills and got good at that, all the other stuff would come.”


That other stuff? It’s definitely come. In their 23 years of business, Windstar Homes has won 67 major regional and national design and building awards and built homes for some of the Bay area’s most well known figures. In 2018 alone, the company won three Aurora Awards (described as the Grammys of home building) and seven American Residential Design Awards, twice as many as any other firm. Tampa’s built-in assets helped serve as a launching pad for Windstar Homes when they opened for business in 1996.

“The opportunity in South Tampa was just a perfect place to set up shop and to create a niche business,” Lesser says. “Tampa’s demographics, affluence, and overall environment makes it a real natural for us to call home base.”

While they’ll build anywhere, Gross says nearly every home Windstar builds is on waterfront property; on the Tampa side, that’s typically on Davis Islands or in the West Shore area fronting Old Tampa Bay. Windstar has been based in Beach Park for years but is in the final stages of building out a brand-new office and design center in Hyde Park.

“We knew that setting up in the Tampa Bay area would allow us to work on both sides of the bay,” Gross says. “There’s so much unbelievable waterfront on both sides.”


Gross joined Lesser at Windstar Homes in 2001, and the duo’s first project was Villa Posada, a 14,000-square-foot property built for former New York Yankees catcher Jorge Posada. Seeing Vil-a Posada was what sold Tampa sleep therapist Shari Mezrah and her husband on Windstar Homes when they were searching for a builder back in the early 2000s. Windstar has now built two homes for the couple, including the new Club Mez (seen throughout these pages).

“When you walk in [to a Windstar Home], it’s the little things,” she says. “We have square hinges on our doors. That’s unique. Those are serious details.” Because Windstar Homes is a design-build firm, they handle every piece of the home construction process, from blueprints to material selection to interior design. For their clients, the process becomes more streamlined and less of a chore, Gross says.

“A lot of times, when people want to build a home, especially a high-end home, they have one of two choices: Either come to a firm like ours that does everything in house, or they have to find their own architect, their own engineer, and their own interior design team,” he says. “Now the [homeowners] have two jobs. They have to manage each of those people as well as go back and do the job they’ve been doing that afforded them the opportunity to build a home like this in the first place.”

“We’ve set up an environment for [clients] where they only have to go one place,” Gross adds. “It just simplifies the process.”


“Bobby and David didn’t do this [home] the way they wanted to do it. They did it the way we wanted to do it, but with their expertise,” Mezrah says. “A lot of architects do throw in the way they do it, and it’s the only way they do it.”

“Every builder has to put a roof on, has to put windows and doors in, has to put exterior cladding on a house,” Lesser says. “But it’s how you use those elements in a very synergistic way that really separates one from the other.”

More than the quality of the work, what sets Windstar apart in the eyes of their clients, Mezrah says, is their level of service. Lesser and Gross will keep in touch with former clients to ensure their satisfaction (It doesn’t hurt they’ve secured a number of repeat customers, like the Mezrahs, this way). “When Windstar builds a home, it’s really not just my home. It’s their home,” Mezrah says. “That’s the one thing that’s impressed us for 17 years. They just keep coming back.”

Lesser calls these kinds of compliments on the service he and Gross strive to provide “music to his ears.”

“That’s the kind of validation we absolutely live for,” he says. “Nobody is doing what we’re doing to the level that we’re doing it,” he adds. “It’s given us a real niche, and that’s why it’s our 23rd year in business, and knock on wood, we’re thriving.”