Job Opportunities

Join our team!

We appreciate your interest in employment with the City of Winter Park. We value our vision, choose the best qualified employees to support this vision, and drive our mission while providing a high level of service to our residents. These individuals must mirror the established city Core Values.

The submission of an application does not obligate the City of Winter Park in any way.


  • Medical
  • Dental
  • Flexible Spending Account
  • Flexible Dependent Care Account
  • Transportation Account
  • Voluntary Life Insurance
  • Short Term Disability
  • Critical Illness Coverage
  • Vision
  • Voluntary Legal Insurance
  • Group Life and AD&D Insurance
  • Long Term Disability (LTD)
  • Paid Time off
  • Long Term Medical
  • Wellbeing Program
  • On-site Wellness Clinic
  • Bereavement
  • Educational Assistance
  • Employee Assistance Program (EAP)

Access Cigna machine-readable filesCigna Healthy Workforce Designation Gold Seal

This link leads to the machine-readable files that have been made available in response to the Federal Transparency in Coverage Rule and includes negotiated service rates and out-of-network allowed amounts between health plans and healthcare providers. The machine-readable files are formatted to allow researchers, regulators and application developers to more easily access and analyze data.

Paid Time Off

The following holidays are observed by the City of Winter Park:

  • New Year’s Day
  • Martin Luther King, Jr. Day
  • Memorial Day
  • Juneteenth
  • Independence Day
  • Labor Day
  • Thanksgiving Day
  • Day after Thanksgiving Day
  • 1/2 Day Christmas Eve
  • Christmas Day
  • Floating Holiday

When a holiday falls on Saturday, the preceding Friday shall be observed as the holiday.
When a holiday falls on Sunday, the following Monday shall be observed as a holiday.


  • Provider, Mission Square (formerly knows as ICMA-RC)
  • 401(a) Money Purchase Plan for Full-time general employees
    • 3% employee contribution mandatory
    • 7% employer match
    • Graduated vesting: 20% per year beginning end of year 1 with 100% vesting at the end of year 5
  • 457 Deferred Compensation Plan for All general employees
    • City Contribution match up to 2% (Exempt employee only)
    • Roth IRA available for employee and spouse
    • To see retirement benefits for Winter Park Police and Fire please refer to their webpage:


Equal Opportunity

The City of Winter Park provides equal employment opportunities to all employees and applicants for employment without regard to race, color, religion, sex, national origin, pregnancy, age, disability, genetic information, marital status, veteran status, or any other category protected by local, state, or federal law related to non-discrimination in employment. This applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation and training.

Reasonable Accommodation

In compliance with the Americans with Disabilities Act as Amended, the city will provide reasonable accommodations to applicants. Arrangements for special accommodations may be made by contacting Human Resources at 407-599-3653.


The City of Winter Park hires only United States citizens and lawfully authorized alien workers. All selected applicants are required to complete Section 1 of federal Form I-9 (Employment Eligibility Verification) and to provide identification and either proof of United States citizenship or proof of authorization to work in the United States.

In addition, we use E-Verify as part of the I-9 process to verify the work eligibility of all new hires. E-Verify is an Internet-based system that compares information from an employee’s Form I-9 to data from U.S. Department of Homeland Security and Social Security Administration records.

The official U.S. E-Verify participation posters for current and prospective employees of their legal rights and protections are available in English or Español.

Veterans Preference

Preference will be provided to qualified veterans and/or their dependents who meet the eligibility requirements set forth by Florida Statute. To be considered for preference, you must indicate on your application and submit a DD 214 form and any service-connected disability documentation (if applicable) for each application submitted prior to the job closing date.

Employee Mission

We are committed to, and take pride in, providing the highest quality services for each other, our residents, business owners and visitors to our city.

Our Core Values

About us

Central Park bench with park behindTake a quick look at our great city to truly appreciate becoming a part of the City of Winter Park family.

Contact Information

Human Resources Division

8 a.m. to 5 p.m.
Monday through Friday

Our Vision

Winter Park is the city of arts and culture, cherishing its traditional scale and charm while building a healthy and sustainable future for all generations.