Amy Calandrino

Amy’s Bio

"Developing ongoing relationships and seeing my clients thrive is what truly drives me. Business owners and investors benefit from my extensive knowledge of inventories, trends, and space. While I have a hyper-local focus in Winter Park and Greater Orlando, I have global reach through alliances with other boutique brokerages and the Commercial Real Estate Supplier Diversity Alliance (CRESDA).  While Central Florida is home, I developed an affinity for Winter Park while earning my degree at Rollins College. Its charm reminds me of my New England roots. Today, I feel blessed to serve many of the area’s businesses and property owners. While providing above-and-beyond service is a priority, my greatest loves are my faith and family. Phil and I cherish raising our two lively children. In my downtime, I also enjoy a round of golf or running a 5k. "

In October 2025,  Amy Calandrino, CCIM, SIOR, has joined Cushman & Wakefield as a Director.

In her new role, Calandrino will provide brokerage, investment and advisory services to clients with a focus on retail, office and mixed-use properties. She has completed hundreds of transactions, valued at more than $100 million, over nearly two decades, representing local, national and global investors, sellers, tenants and landlords.

Prior to joining Cushman & Wakefield, Calandrino owned and operated her own brokerage for 15 years, earning a reputation for results, ethics and a people-first approach. She is a Certified Commercial Investment Member (CCIM), a designee of the Society of Industrial and Office Realtors (SIOR) and has been recognized consistently as a top producer. She is a past President of the Florida CCIM Chapter’s Central District and has received numerous accolades including GlobeSt’s Fifty Under 40, Connect CRE’s Next Generation Award, multiple Circle of Achievement honors, and 2023’s Top Office Producer in Central Florida. She also was named one of Orlando Business Journal’s “Women Who Mean Business” and is a recipient of the publication’s “40 Under 40” award.

Calandrino is a graduate of Rollins College and a committed leader in the Central Florida community. She has served as President of the Leadership Winter Park Alumni Council and was a board member and Secretary for the Park Avenue District, part of the Main Street America program. She also has supported organizations such as the Victim Service Center of Central Florida, Easterseals Florida and Central Florida Women’s League.

In addition to her real estate career and client services, Calandrino co-founded The Calandrino Foundation with her husband, Phil, to support entrepreneurship and help close the wealth gap through education, mentorship and access to opportunity. She is the host of The Performance Mindset Show, a globally ranked top 5 percent podcast featuring candid conversations to help listeners level up in business and life. She is the author of the Amazon bestselling book From Perfect to Real: Ditch Perfection, Shift Your Mindset, and Thrive on Your Terms, which introduces her original SPORT Success System^®.