About

Amy Calandrino is a nationally recognized commercial real estate leader, investor, author, and podcast host known for her strategic insight, client advocacy, and commitment to long-term value creation. As Director at Cushman & Wakefield, Amy provides brokerage, investment, and advisory services with a specialized focus on office, flex, and mixed-use properties, helping occupiers and owners navigate leasing, acquisitions, dispositions, and everything in between. She has completed hundreds of transactions over nearly two decades, representing buyers, sellers, tenants, and landlords across a wide range of deal types and market conditions.

While Amy is deeply connected to local business communities and community-focused projects, her client portfolio also includes national corporations and global institutional firms. Her ability to guide complex transactions across diverse markets makes her a trusted partner to entrepreneurs and investors seeking clarity and strategic growth. Known for her savvy marketing approach and strong social media presence, where she is regularly recognized as a top influencer in commercial real estate, Amy brings a distinct edge to every listing, helping properties move and maximize value for her clients.

Prior to joining Cushman & Wakefield, Amy owned and operated her own brokerage for 15 years, earning a reputation for results, ethics, and a people-first approach. She holds the Certified Commercial Investment Member (CCIM) designation and the SIOR Office Specialist designation, two of the most respected credentials in the industry, and has been consistently recognized as a top producer in her region. Amy is a past President of the Florida CCIM Chapter's Central District and has received numerous accolades including Globe St'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 was also named one of Orlando Business Journal's "Women Who Mean Business" and is a recipient of their "40 Under 40" award.

Amy is a proud graduate of Rollins College and a committed leader in the Central Florida community. She 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 has also supported organizations such as the Victim Service Center of Central Florida, Easterseals Florida, and Central Florida Women's League. Her civic engagement reflects a strong belief in using business to drive positive, lasting impact.

In addition to her real estate work, Amy 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 Long Position, a podcast exploring the intersection of commercial real estate, entrepreneurship, investing, and long-term business strategy, featuring conversations with entrepreneurs, investors, developers, operators, and community builders about the decisions that shape businesses, wealth, and communities over time. She is also 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®.

Amy is a frequent speaker, media contributor, and voice on topics including commercial real estate, entrepreneurship, leadership, and long-term business strategy. Her latest accolades and media appearances can be found at www.amycalandrino.com. She lives in Central Florida with her husband and two children and is passionate about helping others grow, build, and thrive through real estate, leadership, and service.

Awards & Recognition

· Past President of the Florida CCIM Chapter’s Central District 
· 2020 Globe St’s Fifty Under 40
· 2019 Connect CRE’s Next Generation Award 
· 2024’s Top Office Producer in Central Florida by CFCAR
· 2020 Orlando Business Journal’s “Women Who Mean Business” and “40 Under 40”

Clients

· Mosaic Hair Studio & Blowout Bar
· Orlando Pharmacy
· JETechnology Solutions, Inc.
· Transworld Services, Inc.
· Trileaf Corporation
· Annie Mac Home Mortgage

Assignments

· Grafton Wealth Advisors, 1270 N. Orange Avenue, Winter Park, FL 32789 – 5,122 SF
· Brett Bressler, 2709 W. Fairbanks Avenue, Winter Park, FL, 32789 – 5,180 SF

Education

Rollins College English Bachelors of Arts with Writing Minor

Affiliations

· Certified Commercial Investment Member (CCIM)
· Society of Industrial and Office Realtors (SIOR)

Community Involvement

Community Leadership:
· President of the Leadership Winter Park Alumni Council 
· Board member and Secretary for the Park Avenue District
· 2021 “Winter Park Magazine” People to Watch

Community Involvement:
· Victim Service Center of Central Florida
· Easterseals Florida
· Central Florida Women’s League
· Co-founded The Calandrino Foundation, Inc.