Jena Dennis
Owner/Broker | Luxury, Historic & Commercial Real Estate | St. Augustine & St. Johns County
Great Expectations Realty | License BK3387473
Cell 904-806-4274 Office 904-823-3456
Luxury & commercial real estate broker in St. Augustine, Florida
Jena Dennis is the Owner/Broker of Great Expectations Realty in St. Augustine, Florida, with approximately 287 personal closings and more than $211.3 million in personal sales volume. She represents sellers, buyers, and investors in luxury residential, historic, and commercial real estate throughout St. Johns County and Northeast Florida. She has been named to the Jacksonville Real Producers Top 500 four years running (2022–2025), ranking #49 out of more than 12,000 Northeast Florida agents, and was featured on the cover of the April 2025 issue of Jacksonville Real Producers.
Search Northeast Florida listings
Featured areas
Commercial property
Office, retail, industrial, multi-family and development land across Northeast Florida.
View commercialAuction & estate sale services
Great Expectations Auction
Jena Dennis, Owner & Auctioneer
AB4166 / AU3630
Visit GE AuctionLocal nonprofit
Hastings Main Street, Inc.
Jena Dennis, Board Chair
Florida 501(c)(3) nonprofit organization; License CH#71373
Visit Hastings Main StreetAbout Jena Dennis
Jena believes real estate is a relationship business, not a transaction business. Following the Ninja Selling philosophy, she focuses on listening first, giving honest counsel, and serving customers long after closing. Her goal is simple: help every customer realize the full value of their assets and reach their lifelong goals.
Born and raised in the Jacksonville and St. Augustine area, Jena earned three bachelor’s degrees from Florida State University in Marketing, International Business, and Cultural Anthropology. She runs Great Expectations Realty with her husband, Allyn Dennis, and is also the Proprietress of Great Expectations Auction, a separately licensed auction company.
Jena serves as Board Chair of Hastings Main Street, Inc., a nonprofit dedicated to the economic and cultural revitalization of Hastings, and has served on numerous local and state boards. Her lifelong appreciation for antiques, fine art, and Art Nouveau gives her a natural eye for the character and history of St. Augustine’s most distinctive properties.
Work with JenaNotable sales
- The Ellert Estate (Flagler College)
- The Tiberio Mansion
- The Parks Estate on St. George Street (auction)
- Casa Rodriguez, a three-story, 1700s-era property on St. George Street (auction) — Jacksonville Daily Record
- 18 St. George Street (auction)
- 52 St. George Street, a 166-year-old historic home (auction) — News4Jax
On one of her St. George Street sales, Jena recommended auction over a traditional listing. Local opinions placed its value near $1.2 million and the appraisal came in at $1.8 million; the auction brought nearly $2.5 million in under seven minutes.
In the news
- Cover feature: Jena Dennis, April 2025 (Jacksonville Real Producers)
- St. George Street property fetches nearly $2.5 million (The St. Augustine Record)
- 166-year-old home sold at auction (News4Jax)
- Historic St. George Street building sold at auction (Jacksonville Daily Record)
- Historic St. Augustine property auctioned for $2.27 million (Action News Jax)
- Historic building on St. George Street going to auction (WJCT)
- Restaurant site in St. Augustine sells for $3.5 million (Jacksonville Business Journal)
- Industrial acreage in Putnam County sells for almost $4 million (Jacksonville Business Journal)
- Industrial property in Putnam County sells for almost $3 million (Jacksonville Business Journal)
- Boat Drinks owners acquire $2.3 million building in St. Augustine (Jacksonville Business Journal)
- St. Augustine real estate pro: No drastic drop in the market (Jacksonville Business Journal)
- Local real estate pros trying to revitalize Hastings Main Street (Jacksonville Business Journal)
Areas we cover
- Atlantic Beach
- Baldwin
- Beverly Beach
- Bunnell
- Crescent Beach
- Crescent City
- East Palatka
- Flagler Beach
- Flagler Estates
- Fruit Cove
- Hastings
- Interlachen
- Jacksonville
- Jacksonville Beach
- Neptune Beach
- Nocatee
- Palatka
- Palm Coast
- Palm Valley
- Pomona Park
- Sawgrass
- St. Augustine
- St. Augustine Beach
- St. Augustine Shores
- St. Augustine South
- St. Johns
- Vilano Beach
- Welaka
Frequently asked questions
What types of real estate does Jena Dennis handle?
Luxury and oceanfront homes, historic properties, commercial and investment real estate, land, and auction properties.
What areas does Jena Dennis serve?
St. Augustine, St. Johns County, and the greater Northeast Florida region.
How can I contact Jena Dennis?
Call or text 904-806-4274, or visit Great Expectations Realty at 105 S Ponce De Leon Blvd, St. Augustine, FL 32084.
105 South Ponce De Leon Blvd, Saint Augustine, FL 32084
Jena’s cell 904-806-4274 | Office 904-823-3456
MLS information & disclaimers