Lena Michelle Gainer

Lena Michelle Gainer | The Art of Representation

What do Clients Say?

“From the moment we met Lena, we knew we were in expert hands. Building with a custom homebuilder can feel like navigating a maze of options, decisions, and timelines — but Lena’s calm confidence and deep knowledge of the custom-home process made every step feel clear. She anticipated obstacles before they arose, assisted us as we worked through various vendors, and ensured nothing was overlooked. Today, we live in a home that feels thoughtfully curated and perfectly executed — and we credit Lena’s vision for making that possible.” — K&L, Buyers

Buyer Direct

"We came into this project at ****** Yacht Club with more than a few challenges: permitting delays, dock logistics, and the complexity of accommodating our 100-foot vessel. Lena stepped in not just as a sales director, but as an advocate. She coordinated with the dockmaster, orchestrated solutions when permits stalled, and kept us informed every step of the way. In the end, not only did our waterfront home come to life — but our boat moved in seamlessly, too. Today, we couldn’t be happier with how the process unfolded.” — The T Family, Buyers

Buyer Direct

"Our $8 million purchase on The ******Island was one of the most significant investments we’ve ever made. While my team handled many of the details, it was Lena who carried us across the finish line. She stayed intimately involved through contract negotiations, design decisions, and closing logistics, always adding clarity and precision. Her ability to bring high-net-worth buyers and exclusive properties together — even in a fiercely competitive market — is second to none.” —O&S, Buyers

Buyer Direct

“From the very first meeting, we knew Lena approached marketing at a completely different level. Her presentation was flawless — professional imagery, cinematic video, curated copy, and a digital rollout that made our property feel like it belonged in a magazine. More importantly, she handled every showing with discretion and care, ensuring our privacy and schedule were always respected. We never once felt rushed or exposed. Selling a home of this caliber required precision, and Lena delivered it beautifully. We felt protected, represented, and elevated from start to finish.” — Private Seller, Florida

Seller Direct

“When multiple offers came in, Lena’s clarity changed everything. Rather than reacting to the frenzy, she presented a calm, data-driven strategy using her proprietary evaluation tools to assess each buyer’s true position and strength. Her understanding of timing, motivation, and leverage helped us secure not only the best price — but the best terms. What could have been an overwhelming experience became a masterclass in strategy and professionalism. I knew I had the right person in our corner.” — Seller, Pittsburgh

Seller Direct

About Lena

Real estate, to me, is an art form — a harmony of strategy, design, and storytelling that defines the essence of true representation. For over three decades, I’ve collaborated with distinguished builders and developers on new construction and custom home projects, creating residences that are both intelligent in design and remarkable in execution.

Rooted in high-end real estate and new home development, my experience spans multiple markets — from waterfront homes in Tampa and Palm Beach to architectural estates and contemporary enclaves throughout Pittsburgh and Sarasota. I understand how to interpret a floor plan, a finish schedule, or a buyer’s unspoken vision, and transform it into a lifestyle that feels both intentional and effortless.

Through the precision of AI-powered real estate platforms paired with genuine human connection, I deliver representation defined by foresight, integrity, and ease. With more than one billion dollars in collective real estate sales volume — through my own production and the elite on-site sales teams I’ve led — my mission remains the same: to curate experiences that honor craftsmanship, elevate property value, and tell a story worth remembering.