Anna Olcese

Owner, Realtor®


About Anna

Anna is a Miami native who relocated to Gainesville over 20 years ago. A serial entrepreneur, Anna started several companies during the past couple of decades in the fields of real estate, marketing and communications, corporate event management, and publishing.

After graduating from UF and moving to Atlanta, Anna returned to Gainesville in 1998 as a trailing spouse. Consequently, she understands the challenges of relocating to a new city, which is the number one reason that she has dedicated the majority of her real estate career to serving the relocation and executive real estate markets.

As both owner of Segway Group, which specializes in helping organizations with their recruitment and relocation endeavors and as a Realtor, Anna works closely with UF, UF Health, government entities, tech companies, and other businesses to help recruit top talent from around the globe and then assist them with their real estate needs. Her concierge-style approach to luxury experiences for buyers, sellers, and referral partners have earned me the reputation as the go-to person to assist VIP candidates and new hires. This has helped Anna to forge a number of strong relationships with newcomers to the area, which in turn allows her to grow a network of support for future residents.

In February 2021 Anna moved to Engel & Volkers from Keller Williams, where she had started my real estate career and subsequently founded a top producing 10-person team. The unexpected move resulted after she was approached by Engel & Volkers and learned about their philosophy of making the luxury experience accessible to individuals at any stage in life. This perfectly aligns with the way I’ve always conducted business.

In addition to helping her customers buy and sell real estate, Anna’s “Let’s Talk Real Estate” podcast helps to educate the audience about a variety of real estate-related topics, local and national market conditions, and how the area’s growth and opportunities compare to other cities nationwide. Lastly, by combining her publishing and marketing backgrounds, Anna has also created videos to showcase the area’s natural beauty, housing opportunities, businesses, and the people who make the Gainesville area what it is today and what it will become tomorrow.