About Anna Olcese


Agent Details

Meet Anna


Anna began her real estate career in 2015 and quickly became an award-winning real estate advisor. In 2017 she co-founded a 10-person team with nearly $30 million in yearly sales and in 2021 she joined Engel & Völkers Gainesville, where she was named the company’s top producing single agent both in 2021 and 2022. She’s also been the recipient of the Engel & Völkers Americas Diamond Elite and Ruby Elite awards.


A Miami native who moved to Gainesville in 1998 as a trailing spouse, Anna understands what it’s like to relocate to a new, and often smaller, area of the world. Today, Anna is one of the top relocation specialists in Gainesville and all of Alachua County, and both as a Real Estate Advisor with Engel & Völkers and through her relocation services company, Segway Group, guides newcomers and helps organizations with their recruitment and relocation endeavors. Anna works closely with the University of Florida, 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.


In addition to working with relocation clients, Anna works with executive-level sellers and buyers, specializing in the luxury market. She also has a special place in her heart for first-time buyers, and enjoys helping them attain their homeownership dreams. Lastly, Anna works with elder care attorneys and financial advisors on several probate sales every year. 


Anna attributes her success to the fact that she’s different. The buyers and sellers with whom she works are provided with a bespoke experience, whether they are buying their first home or selling a

luxury property. Luxury is a service, not a price point. That is not a mantra. That’s the way Anna does business.


“Most importantly, I will never compromise my values for personal gain because my reputation as an honorable and trustworthy individual is sacred to me,” Anna says. “There are no exceptions to the level of service I provide. ‘Above and beyond’ is the standard by which I operate, and I provide that level of service to everyone I work with.”


For nearly 20 years prior to starting her real estate career, Anna owned a variety of companies in the marketing, public relations, and event management sectors, freelanced as a writer for various publications and was the editor of two, allowing her to forge strong relationships with community and business leaders in the Greater Gainesville and Alachua County area.


Going back to her marketing and publishing roots, Anna started a podcast in 2020 called “Let’s Talk Real Estate,” which touches on 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. 


In her spare time, Anna travels the globe with her husband and looks forward to moving overseas when they retire…not that she ever plans on really retiring because she can’t imagine a life without her real estate career.

Work With Anna

Get assistance in determining current property value, crafting a competitive offer, writing and negotiating a contract, and much more. Contact me today.

Follow Me on Instagram


Powell W.

Powell W.

Anna Olcese was great to work with. She made buying my first house an easy experience. She answered questions about neighborhoods and taught me a lot of what I should be looking for as we toured the house along with being extre...
Read More
Mat & Cora

Mat & Cora

Anna is extremely attentive, responsive, and very easy to work with. She is extremely knowledgeable in her field and knows everything about the Gainesville Area and we would highly recommend her to anyone who wants to buy or se...
Read More


We were recommended to Anna by our daughter and son-in-law who Anna helped sell their home a few years ago. She was very knowledgeable and accommodating when showing us homes. She was always on top of anything that came up, wit...
Read More