City of Winter Garden, FL

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A charming little city with a juicy past



"We make every customer feel important and cared for, find creative solutions with a can-do attitude, and follow the Winter Garden Way."

* Ownership * Responsive * Respectful * Professional
Provide service delivery that will create service wins for both our internal and external customers.

Please click here to view and apply on-line for a current vacancy.

Fire Department Job Information: Click Here

Applications may also be completed at:

Winter Garden City Hall
300 West Plant Street
Winter Garden, FL 34787
Attn: Human Resources

Persons needing assistance or accommodation in accessing the application process should contact Human Resources at 407-656-4111.


The City of Winter Garden offers equal employment opportunity to all persons regardless of race, color, religion, sex, national origin, age, or disability. Veteran's preference is given per State Statute on initial hire (documentation (DD214 or VA Letter of Disability) must be included with the application form).

Applicants offered employment will be subject to background investigation which may include criminal, academic, employment and credit. Additionally, those applicants offered employment will be required to successfully pass a pre-employment physical and may be required to pass a drug test.


  • Medical Insurance: Pre-tax Medical coverage is provided for all full time employees with an option of 3 medical plans. When all wellness points are received, the employee only premium is paid 100% by the City for both the Choice Base and High Deductible Plans. The City also provides partial contribution for dependent coverage.
  • Life Insurance: Life insurance is provided in an amount equal to double an employee's annual salary up to a maximum of $250,000, with the premium paid 100% by the City.
  • Flexible Spending Accounts (FSA): Employees may contribute to pre-tax Health Care ($2,550 annual maximum) and Dependent Care ($5,000 annual maximum or $2,500 if married and filing separately) FSAs to pay eligible health and dependent care expenses.
  • Short Term Disability: Pre-tax, employee-paid short term disability coverage is available for all full-time employees.
  • Long Term Disability: Coverage is provided for all full-time employees with the premium paid 100% by the City.
  • Dental, Vision, Voluntary Life Insurance and Other Cafeteria Group Plans are available through employee payroll deduction, with the premium paid by the employee.
  • Educational Reimbursement: Employees are eligible for educational assistance (tuition and books) related to ongoing education at commissioned colleges and universities at the current UCF per credit hour rates after a continuing employment agreement is approved and a final grade of C or better is achieved.
  • Retirement: The City has a retirement plan vesting after 5 years of service for General employees and after 6 years of service for Police officers and Firefighters. A deferred compensation option is also available.
  • Holidays: All full-time employees receive nine (9) paid holidays and one (1) personal day per year.
  • Sick Leave: All regular full-time employees are eligible for accrued sick leave at the rate of eight (8) hours per month (10.75 hours per month for those with a scheduled work week of 56 hours) and usable after the successful completion of a six-month training period. Sick Leave may be accrued from year to year with certain caps and may be utilized for personal sickness, treatment by a healthcare professional, and for illness of the employee's immediate family requiring personal care from the employee.
  • Vacation: All regular full-time and part-time employees are eligible for accrued vacation, which can be used after the successful completion of a six month training period. Note that although Police and Fire have a training period of one year, they are also eligible to begin taking accrued leave after completing six months of service.
  • Sick Leave Sharing For Full-Time Non-Probationary Employees: Approval from the City Manager is required.
  • Clothing Allowance or Uniforms Supplied