Some people discover the Emerald Coast on vacation and never quite forget it. For Penny Jackson, that story began in the late 1990s when she and her husband traveled from Birmingham to Sandestin for work conferences. What started as a professional obligation quickly became something more personal. Nearly three decades later, they still call the area home.
A graduate of Auburn University with a degree in hotel and restaurant management, Penny built the foundation of her career in hospitality before transitioning into real estate. In 1999, she joined Sandestin Golf and Beach Resort, where she worked across rental management, operations, development coordination, and ultimately group sales, serving as director of group sales for the resort. The role gave her an unusually deep understanding of the Emerald Coast’s communities, neighborhoods, homeowners associations, and evolving resort lifestyle long before she officially entered real estate.
At the same time, Penny and her husband were developing spec homes throughout WaterColor and neighboring 30A communities, giving her firsthand experience in construction, planning, design, and the details that transform a house into a home. By the time she launched her real estate career, she was already deeply connected to the area — not only geographically, but personally and professionally.
Today, Penny brings that layered perspective to every client relationship. Her background in hospitality shaped her approach to service, while her years inside resort operations gave her a practical understanding of how communities truly function beyond the listing description. She believes the most valuable information often lives outside the marketing photos: HOA structures, lifestyle nuances, rental dynamics, and the subtle differences between neighborhoods that only longtime locals tend to understand.
Known for her warmth, attentiveness, and thoughtful guidance, Penny works closely with buyers and sellers throughout Sandestin, Miramar Beach, Destin, and along 30A. She has a particular connection with empty nesters and second-home buyers navigating a new chapter in life, as well as vacation rental investors seeking properties that balance financial performance with genuine personal enjoyment. Her experience in resort rental management allows her to offer insights that extend beyond aesthetics and square footage to how a property can function as both an investment and a place to build memories.
Outside of real estate, Penny’s life revolves around family, travel, food, and community. She and her husband recently celebrated 30 years of marriage and are proud parents of two sons, both of whom attended Florida Atlantic University. A devoted Auburn football fan and loyal supporter of the New Orleans Saints, she also loves cooking Mediterranean-inspired meals, discovering locally owned restaurants, and planning her eventual trip to Antarctica — the final continent on her travel list.
At home, she can usually be found with Cooper, her beloved Puggle and unofficial kitchen supervisor, never far from her side.
For Penny, home has always meant more than ownership. It is the place where people gather, recharge, celebrate milestones, and create the memories that shape a life. Helping clients find that feeling — and guiding them through the process with care and clarity — remains the part of the work she values most.
Home Types:
Condo, Townhouse, House
Years of Experience:
13
Education:
B.S. Auburn University
