At only 20 years old, Hailey Kendall dove headfirst into Sarasota’s high-end real estate market out of her love for the artistry and stories behind Florida homes.
Born and raised in Florida, Kendall grew up studying historic houses and market trends in the state, with a keen interest in architecture — long before becoming a real estate agent. She graduated early from Florida Atlantic University with a degree in business administration, management and entrepreneurship to immerse herself in the field.
What started as cinematic videography featuring multimillion-dollar home tours and helping market properties through a self-created brand has transformed into a full-time career where she exclusively represents sellers of luxury properties. As a Broker
Associate for William Raveis Real Estate with four years in the industry, she specializes in waterfront and architecturally significant homes in Sarasota, focusing on the stories behind the property line.
Kendall said she has set out to "define the next generation of luxury real estate," most recently selling a vacant plot of land, located at 4214 Higel Ave., on Siesta Key's waterfront for $9.2 million, which Kendall said set a record for the highest-priced sale of a vacant parcel on the barrier island.
At just 24 years old, she is representing one of Siesta Key's most prominent properties right next door, the Higel Estate.
Defined by 290 feet of private beach frontage, native tropical landscaping and old Florida-style architecture, the Higel Estate is a 2.64-acre compound on one of Sarasota's most coveted barrier islands. Kendall told the Herald-Tribune that the exclusive luxury listing is the largest of her career yet, hitting the market Oct. 15 for $25.5 million.
The "unusually large expanse of Gulf-front property" brings together three parcels at 4200, 4189 and 4185 Shell Road that were previously held separately. According to marketing materials, the opportunity to acquire multiple properties at this scale is a "fundamentally different proposition from a conventional waterfront home."
Built in 1953, the two residences on the property pull from the island's architectural and residential history, which Kendall said is part of what makes the estate so significant, along with the land scale and Gulf-front setting.
"The main residence really captivates that sense of Old Florida living and what Siesta Key was like back in the 1950s," Kendall said. "The owners have done an incredible job preserving the history of this property while giving it more of a modern touch."
The four-bedroom, four-and-a-half-bathroom home spans 2,937 square feet, with vintage hardwood flooring and ceilings throughout. The property additionally features a two-bedroom guest residence with similar characteristics and an outdoor pool.
Architectural plans for a roughly 14,000-square-foot residence, designed by award-winning, Southwest Florida-based MHK Architecture, are included in the sale. The transaction also includes an alternative site plan, an 8,000-square-foot design to complement and preserve the existing main residence and guest house.
Kendall said the contiguous property and included plans provide a rare opportunity for "new architectural expression."
"The existing landscape, Gulf frontage and historic structures provide a distinctive starting point for considering the relationship between architecture, nature and the coast," Kendall said. "This is not simply a Gulf-front compound. It is a piece of Siesta Key with the opportunity for its next owner to determine what comes next."
Representing this particular property is not only a milestone for Kendall's career but it is also a reminder of why she started. She said she learned so much about the area during her research into the rich history of Higel Avenue and Siesta Key, leading to a deeper understanding of the property and shaping her marketing approach.
"I have learned so much about the history of Siesta Key," Kendall said. "This incredible piece of property carries that history forward, being here on Higel Avenue."
The Higel Estate is located along Higel Avenue, which carries the name of Harry Higel, a prominent Sarasota entrepreneur and developer. He is often credited with shaping the city's growth and establishing the early tourism economy on Siesta Key.
Kendall said the property "holds a distinctive place in the history of Siesta Key," and that its location, old Florida-style architecture and placement overlooking the Gulf are emblematic of the vision that Higel had for Siesta Key's potential.
Sarasota's luxury market
The new luxury property listing comes as a waterfront Siesta Key home sold for $26 million in cash last month, making it Sarasota County’s most expensive home sale so far in 2026. Additionally, less than two weeks before, the $21.95 million sale of Crystal Waters at 8501 Midnight Pass Road, also on Siesta Key, broke another area record.
Overall, Sarasota's ultra-luxury market has seen more demand in recent months, despite elevated mortgage rates and broader affordability pressures affecting other sectors of the real estate market. This is something that Kendall said she has experienced firsthand, being immersed in the luxury real estate sphere.
"The Sarasota luxury market is really hot right now," Kendall said. "If you compare it to other markets like Naples or Manalapan, if the Sarasota, Siesta Key and Longboat Key markets are continuing in that same direction, these properties that are selling now could be worth significantly more in a couple years."
Luxury real estate platform Housing Info reports that, despite market pressures on the greater housing market, luxury listings continue to thrive due to the patterns of buyers and financing trends in that market sector, "making it less sensitive to affordability crises, interest rate volatility, and local supply-demand imbalances."
Additionally, cash sales have also seen an increase, which is often indicative of how active investors are in the market, according to a report from Florida Realtors.
“Investors are far more likely to have the funds to purchase a home available up front, whereas the typical homebuyer requires a mortgage or some other form of financing,” Florida Realtors Chief Economist Brad O’Connor said in a prepared statement.
On a state level, Florida's luxury housing sector has surged this year, with multimillion-dollar home sales recording some of the strongest gains in the market, according to recent reports.
Kendal Asbury is the real estate and development reporter for the Sarasota Herald-Tribune. Have an idea, tip or question about development? Send her an email at kasbury@usatodayco.com. Connect with her on LinkedIn or follow her on Instagram @wordsbykendal, and support local journalism by subscribing to the Herald-Tribune.
This article originally appeared on Sarasota Herald-Tribune: Meet the 24-year-old agent listing a $25.5M estate on Siesta Key
