About Anna Olcese

Here’s a little about me that will help you learn about my business philosophy, my past and present, my experience, and what I can bring to the table to help you with your real estate needs. If it appeals to you and you think that our personalities would be a good fit for one another, then it would be great to chat because I’d love to get to know you and see how we can go on your real estate journey together. 

How I Serve

My success is rooted in a tailored approach to real estate. Every client receives the same high level of service, regardless of price point, catered to meet their specific needs. To me, luxury is a service, not a number—it’s simply how I do business.

My reputation is sacred to me and I will never compromise my values for personal gain. “Above and beyond” isn’t optional—it’s the standard by which I operate.

Who I Serve

Originally from Miami, I relocated to Gainesville in 1998 and understand firsthand what it’s like to move to a new—and often smaller—market. Today, I’m one of the leading relocation specialists in Gainesville and Alachua County. Through my work with Engel & Völkers and my relocation services company, Segway Group, I help individuals and organizations navigate recruitment and relocation. I work closely with the University of Florida, UF Health, government entities, tech companies, and other businesses to attract top talent from around the world and support them with their real estate needs.

In addition to relocation services, I work with executive-level buyers and sellers, with a strong focus on the luxury market. I also have a special place in my heart for first-time buyers and enjoy helping them achieve their homeownership goals. Additionally, I regularly collaborate with elder care attorneys and financial advisors on probate sales as well.

Other than Real Estate…

Before transitioning into real estate, I spent nearly 20 years owning and operating businesses in marketing, public relations, and event management, and working as a writer and editor for multiple publications. Those experiences helped me build strong relationships throughout the Greater Gainesville and Alachua County communities.

In 2020, I launched my podcast, Let’s Talk Real Estate, where I discuss real estate topics, local and national market trends, and how our region’s growth and opportunities compare to other cities across the country.

In My Spare Time

Outside of work, I love traveling the world with my husband and dream of living overseas one day—though I can’t imagine ever truly retiring from a career I’m so passionate about. I also cherish spending time with our adult daughter whenever I get the chance to visit her. And if you’ve ever watched my Wine Wednesday series on social media, you already know that exploring new wines—and “pairing” them with homes or cities—is another favorite pastime of mine.

Stats

• January 2015: Began my real estate career

• January 2017: Co-founded a 10-person team producing nearly $30 million in annual sales

• October 2020: Amicably parted ways with my partners and dissolved the team

• February 2021: Joined Engel & Völkers Gainesville as a single agent

• August 2023: Founded the Olcese Group at Engel & Völkers

• Engel & Völkers Gainesville Awards: Top-Producing Agent, 2021, 2022, 2023, and 2025

• Engel & Volkers Americas Awards: Diamond Elite (2021) and Ruby Elite awards (2022, 2023, 2024, 2025)

• Engel & Völkers Florida Recognition: For 2025, ranked #35 among all Engel & Völkers advisors in the State of Florida