Jacksonville Real Producers | Jena Dennis | April 2025

Jena Dennis

By Nick Ingrisani | Photos by The Real Estateographers

Born and raised in Jacksonville, Jena Dennis has always been deeply connected to the Northeast Florida area. After qualifying for early admission, she earned her associate’s degree while in high school and went on to earn three degrees in international business, cultural anthropology, and marketing from Florida State University.

“I felt like I branched out and explored what I wanted to do and where I wanted to be. I was passionate about the degrees I picked, they helped me broaden my horizons,” says Jena.

After graduating in the wake of 9/11, Jena initially planned to launch an importing company. However, recognizing the challenges of international business travel at that time, she pivoted and opened her first business — an antique store. Her new path turned into a long-term passion that progressed naturally into the world of estate sales and auctions. Over time, she expanded her expertise, acquiring multiple business licenses and diversifying her portfolio.

Her introduction to real estate came through her husband, Allyn, a seasoned broker. Together, they merged their businesses, creating a firm that handles real estate transactions and specializes in estate sales, auctions, and business brokering. Their unique approach allows them to manage everything from selling homes and commercial properties to liquidating assets, making them a go-to resource for clients navigating complex transitions.

“Our motto is we can sell your home or business and everything in it. We work with a lot of attorneys and can do court-ordered sales, divorce settlements… I’ve literally sold everything that could be considered personal property and assets.”

The great thing about loving what you do is you never feel like you need to retire. I’m very passionate about this work.

Currently, Jena owns and operates a boutique brokerage with a team of 23 agents. Her expertise spans residential, commercial, and land sales, with a particular focus on historic properties in downtown St. Augustine and the revitalization of Hastings, Florida. Jena is the board chair for the Hastings Main Street non-profit, which is working to revitalize the community both historically and economically. Over the past two years, she and her husband have played a pivotal role in transforming Hastings’ Main Street, acquiring and renovating six buildings. What was once an area with 80% vacancy now boasts a 90% occupancy rate, thanks to both their efforts and community support.

“We’ve really turned the area around and have been getting a lot of grant funding — statewide and federal — to help rebuild the infrastructure of the community as well. It’s a super rewarding passion project.”

One of their most ambitious projects is the restoration of an 18,000-square-foot historic building, which they are converting into an event venue for weddings, corporate gatherings, and community functions. Beyond real estate transactions, Jena’s passion lies in preserving history and fostering economic growth within her community.

Her approach to real estate extends far beyond buying and selling homes. She is passionate about educating her clients on how real estate can be a vehicle for financial independence. Whether guiding a first-time buyer toward their dream home or helping an investor maximize

“Real estate can give you financial freedom through passive income that many people never even dreamed was possible. I have so many clients I initially help them buy a house, then we talk about investment properties. Whether it’s buying and flipping or renovating into a long-term hold, people can retire much earlier than they thought by diversifying their investments. It’s such a passion of mine to dramatically change people’s lives by helping them take advantage of the assets they have.”

One of the defining factors of Jena’s success is her breadth of knowledge and experience. Having navigated nearly every facet of the real estate industry — from sales and development to rezoning and asset liquidation — she brings a level of expertise that sets her apart.

“I’ve been through so many facets of this industry and all of that knowledge and experience elevates the services I can provide. I’m not here to just problem solve and troubleshoot. I’m here to take it to another level and help each client excel and take advantage of opportunities within each transaction It’s a fun challenge to take something that seems like a normal transaction and elevate it.”

Outside of running her businesses, Jena prioritizes time with her family. She and her husband, have three children, ages 11, 9, and 7, who are already learning the ins and outs of the family business. Integrating family into their entrepreneurial endeavors is a cornerstone of their values, ensuring that their children understand the importance of hard work and community involvement.

From building businesses to restoring communities, Jena’s impact is felt across multiple industries and throughout Northeast Florida. Her journey is a powerful example of how passion, adaptability, and a deep commitment to service can transform not just individual lives, but entire communities.

It’s a fun challenge to take something that seems like a normal transaction and elevate it.