Jessica Kenney

Agent Details

About Jessica

Jessica Kenney bought her first home in Sarasota at nineteen and her first investment property at twenty-one — long before she ever thought about a career in real estate. Since then, she's spent over ten years and 100+ transactions turning that early love of homes and neighborhoods into a career built on trust, not sales pitches — because what she cares about most is making sure people walk away from a real estate decision feeling confident, not just closed. Jessica is a Sarasota native, which means she doesn't just know the market — she knows the area. From Sarasota and Bradenton to Lakewood Ranch and Venice, she brings a lifetime of local knowledge to every buyer and seller she works with, whether they've lived here for decades or are just discovering it for the first time. Jessica graduated from the University of South Florida with a B.S. in Business and Finance before starting a career in banking, where she spent ten years working across loans, investments, and insurance. That background still shapes how she works today: she believes in giving clients the real, honest financial picture of what they're walking into, not just telling people what they want to hear. Jessica works across a wide range of property types and transactions — residential homes, condos, new construction, investment properties, 1031 exchanges, and short sales or bank-owned homes throughout Southwest Florida. Whatever the situation, she's built a power team around her clients: inspectors, insurers, attorneys, title companies, and lenders covering everything from conventional loans to private money, portfolio lending, and down payment assistance — so there's rarely a deal she can't help structure. Jessica is a REALTOR® and member of the REALTOR® Association of Sarasota and Manatee (RASM) and the National Association of REALTORS®. She's also proud to have experience working with veteran clients, helping guide them through the specific benefits and processes available to them. Giving back is a family value for Jessica. She sits on the Board of Casting For The Kids, a local childhood cancer charity, while her husband Lyle serves on the Board of Operation Patriot Support — and together they're both active with Operation Second Chance, supporting veterans and their families. Outside of work, Jessica spends her time boating with Lyle and their two kids, Colton and Aubree — whether that's here in Sarasota or at their lake house on Lake Sinclair in Georgia.

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