About Me

Jolene Sheive currently represents the District 3 seat on the Osceola County School Board following her appointment in 2026. A lifelong resident of Osceola County and a product of the Osceola County School District, Jolene attended Reedy Creek Elementary, Thacker Avenue Elementary, Denn John Middle School, and Osceola High School—Go Kowboys! Having attended our local schools, she has a deep personal connection to the district and a strong appreciation for the role educators play in shaping students and strengthening the community.

Professionally, Jolene is the Broker/Owner of Legacy Realty of Central Florida and a Partner at SLS Investments of Central Florida, a local real estate investment firm based in Osceola County. She began her career in the title insurance industry and spent 15 years with Stewart Title before obtaining her real estate license, later earning her broker’s license, and going on to open her own real estate brokerage and property management company. Today, she leads and supports clients and investors throughout Central Florida.

With a strong desire to give back to the community that gave so much to her and helped shape her personally and professionally, Jolene is actively involved in numerous civic and leadership roles. She currently serves on the Osceola County Education Foundation, is serving her second term on the Osceola County Planning Commission, is a Board Member of the Osceola County Chamber of Commerce, Vice Chair of the St. Cloud Chamber of Commerce, and Community Service Chair for the Rotary Club of Kissimmee. She also sat on the Junior Achievement of Osceola County Advisory Committee. Her blend of professional leadership and civic engagement informs her service on the School Board and her commitment to students, families, educators, and community stakeholders.

Jolene is the proud mom of a daughter who is a graduate of St. Cloud High School and now attends Auburn University, as well as a 9-year-old son who keeps her busy with sporting events and activities. In her spare time, she enjoys being on the water, cheering on her children, reading, and traveling with friends and family.