Jessica Gregory – REALTOR®, Cowford Realty & Design

Jessica’s career has always centered around helping people transform their lives — whether through health, wellness, or now, homeownership. With more than 20 years of experience in corporate finance, sales leadership, and small business ownership, real estate was a natural next step. It allows her to combine her love for people, her business savvy, and her deep connection to Jacksonville’s neighborhoods.

Jessica understands that buying or selling a home is about more than just the transaction — it’s a major life event. Her goal is to truly understand her clients’ needs and guide them through each step with confidence, care, and attention to detail. Her diverse background taught her how to lead teams, manage complex projects, and create meaningful experiences — skills she now uses to help her customers find the right fit in both home and community.

An active member of Riverside Avondale Preservation (RAP), Jessica is passionate about supporting her community and strengthening the bond between residents and small businesses. She believes that thriving communities are built when people invest in where they live, and she loves helping her clients become part of that story.

When she's not working, Jessica enjoys walking her dogs, trying local restaurants, and attending community events.

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Fun Facts

What’s one cause you’re passionate about? Empowering women in transition — whether that’s through business, health, or new beginnings in a home of their own.

Favorite restaurant in Jax. For everyday eats, Pine Grove Deli — a small, locally owned neighborhood favorite. For special occasions, Cowford Chophouse downtown for the incredible food and vibrant atmosphere.

Your absolute favorite spot in Jacksonville? The Riverside Arts Market on Saturdays — it never gets old.

If you won the lottery, what would you do with your winnings? Travel throughout the United States in an RV with Lulu and Carter, discovering National Parks and charming small towns along your route, as well as traveling to international destinations. Travel opens your eyes and expands your perspective.

What is your real-life superpower? Connecting with people. Jessica never meets a stranger and genuinely enjoys learning everyone’s story.

What’s your favorite room in a house? The kitchen — it’s the heart of the home, where connection and conversation happen naturally.