About Shayla Gregory

Shayla A. Gregory is a Fort Lauderdale-based Realtor, real estate investor, and vacation rental owner with over 20 years of experience in strategic marketing, promotion planning, and media leadership. She holds degrees in Communications and Studio Art from Boston College.

Prior to real estate, Shayla spent two decades at HBO as Manager of Promotion Planning & Strategy, where she developed and executed campaigns for some of cable television’s most acclaimed and groundbreaking series. She also brings experience from the National Basketball Association, further strengthening her background in marketing, communications, and brand strategy.

Today, Shayla blends her media and marketing expertise with hands-on real estate experience as an investor and vacation rental owner. Her work spans property acquisition, renovations, income-producing properties, and short-term rental operations, giving her a well-rounded perspective on both residential and investment real estate.

She works with buyers, sellers, and investors, offering a strategic approach, strong negotiation skills, and practical market insight. Shayla is dedicated to helping clients make informed decisions and move through every transaction with confidence.