Amy Calandrino at Cushman & Wakefield

About Us

Amy Calandrino is a nationally recognized commercial real estate advisor based in Winter Park, Florida, serving business owners, families, and investors throughout Central Florida and beyond. A proud Rollins College graduate, Amy has nearly two decades of experience advising clients on office, retail, mixed-use, and urban infill real estate with a focus on strategic occupier representation, investment guidance, and long-term wealth creation.

Amy works closely with small to mid-sized businesses and family-owned companies as they navigate expansion, relocation, right-sizing, acquisition, redevelopment, and disposition. Her advisory approach combines market analytics, financial insight, and hands-on deal execution to help clients align real estate decisions with broader business and family objectives.

As a Certified Commercial Investment Member (CCIM) and SIOR designee, Amy brings institutional-level expertise while maintaining a highly personal, relationship-driven approach. She has completed hundreds of transactions and is known for solving complex challenges, structuring creative solutions, and collaborating seamlessly with clients’ legal, financial, and design teams.

Deeply rooted in the Winter Park community, Amy has served in leadership and advisory roles with both the Park Avenue District and the Winter Park Chamber of Commerce. She is also a podcast host, author, and active advocate for entrepreneurs and locally driven commercial districts, helping shape environments where businesses and families can thrive.