Maintenance Operator II (Roadways/Sidewalks/Trees)

Current Job Postings
All positions currently accepting applications are listed below. Applications can be completed online or in person at our Human Resources Office at 500 Third Street NW. Should you have any questions, please feel free to contact the Human Resources Team at 863-291-5650 or humanresources@mywinterhaven.com.
Would you like to be notified when we post new jobs? Click the Notify Me button to choose which jobs you’d like to receive notifications for and how you’d like to be notified.
RSS
Notify Me®
Search Jobs By
Filter by category
All Categories
Full Time (10)
Internal-Only Opportunities (0)
Internships (0)
Part-Time (2)
Summer (0)
Search
Steps
1. Listing Information This section is complete current step
2. Job Details This section is complete
3. Preview and Submit This section is complete
Listing Information
Category*
Advertising and PR Services
Aerospace and Defense
Banking Business Services
Computer/IT Services
Construction
Education
Engineering Services
Financial Services
Government and Military
Healthcare Services
Insurance
Internet Services
Nonprofit
Other/Not Classified
Printing and Publishing
Real Estate
Restaurant/Food Services
Retail
Choose from Full List
Display*
Display Starts
October
2026
Calendar Sun Mon Tue Wed Thu Fri Sat
27
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
7
Display For
1 week - Free 1 month - Free 3 months - Free 1 year - Free
Feature this listing for free What's this?
Featured job listings display on the top of all job listings and are designed to stand out from the others.
Continue
Job Details
Job Title*
Job ID
Description
Salary
Qualifications
Special Requirements
Miscellaneous
Continue |Go Back
Preview and Submit
job listing from to
Featured
Total
After completing all the steps, click Preview to open a preview of your listing in a new window or click Proceed to Checkout where you can purchase the listing for the duration you specified.
Preview Proceed to Checkout Pay Later Cancel
Full Time
◄ Back to All Categories
Maintenance Operator II (Roadways/Sidewalks/Trees)
Are you someone who enjoys working outdoors, making a visible impact in your community, and taking pride in keeping public spaces safe, clean, and beautiful? We’re looking for a hands-on, dedicated Maintenance Operator to help maintain and enhance our sidewalks, roadways, and trees.
Job Title: Maintenance Operator II (Roadways/Sidewalks/Trees)
Category: Full-Time
Application Closing Date: October 25, 2026, 5:00 p.m.
Application: Click Here
Salary And Benefits
$18.10 Per Hour Minimum
Annual Step for Performance Pay Adjustments
12 Paid Holidays Per Year
12 Vacation Days Minimum, Earned Per Year
12 Sick Days Earned Per Year
Medical, Dental, Vision, and Life Insurance Benefits
401(a) Retirement Plan and Social Security Coverage
457 Deferred Plan Options
Education/Tuition Assistance Program; and Training and Development Opportunities
Employee Assistance Program – to include Mental Health Assistance/Services
APPLY NOW
Essential Job Functions
Works as part of a compact multi-talented team in a growing community maintaining, repairing, and improving roadways, pedestrian infrastructure, and providing sustainability for a healthier urban canopy throughout the City.
Roadways: Duties include but are not limited to preforming maintenance and repairs on a revolving repair and improvement worklist, and performing scheduled routing maintenance of equipment used to perform job duties. Functions also include providing support on utility locates and ordering materials needed to complete a proper roadway repair or new installation, collaborating on and reviewing project plans, helping to track project progress from conceptualization through finalization, and ensuring a safe working environment. This position functions as part of a multi-disciplined team and will also be involved in other aspects of maintaining public infrastructure.
Sidewalks: Supports the Division by working to construct, maintain, repair, and improve the City’s pedestrian infrastructure. Duties to include but are not limited to planning and constructing new pedestrian connections, performing maintenance and repairs on a revolving repair and improvement worklist, and performing scheduled routing maintenance of equipment used to perform job duties. Functions also include providing support on utility locates and ordering materials needed to complete a proper sidewalk repair or new installation, collaborating on and reviewing project plans, helping to track project progress from conceptualization through finalization, and ensuring a safe working environment. This position functions as part of a multi-disciplined team and will also be involved in other aspects of maintaining public infrastructure.
Trees: Supports the Division and crew leader as a vital member of the tree maintenance team, contributing to the care, preservation, and enhancement of the City's urban tree canopy.
Responsibilities include but are not limited to planning and executing tree maintenance tasks, performing routine and corrective tree care, maintaining and servicing equipment essential to the job, and ensuring the safety of the crew and the public during tree-related activities.
In addition to tree-related duties, this role collaborates on project plans and contributes to the monitoring of project progression, from initial planning to completion. Procuring necessary materials for tree care operations and assisting in utility locates are also essential job functions.
Must be available to perform essential job function outside of regular work hours responding to emergency situations, mostly based on “subject to call” scheduling. This is not intended to be an all-inclusive listing of essential job functions; the performance of other essential functions may be required.
Knowledge, Skills & Abilities
Roadways Maintenance
Knowledge and experience with the operation of related tools (shovels, circular saws, demo saws, tampers, levels, tape-measures, etc.) and equipment (backhoe, skid-steer, mini-track hoe, etc.
Knowledge of construction operations (quantity estimation, installing or repairing proper roadway infrastructure).
Continuing education in constructing roadway improvements will be a requirement of this role.
Sidewalks
Knowledge and experience with the operation of masonry craftsmanship related tools (shovels, circular saws, demo saws, tampers, trowels, levels, tape-measures, etc.) and equipment (backhoe, skid-steer, mini-track hoe, etc.)
Knowledge of construction operations (quantity estimation, installing or repairing proper ADA compliant sidewalk infrastructure, curb ramps), and the knowledge and understanding of the FDOT Design Standards and Specifications for proper sidewalk and ramp application.
Continuing education in constructing pedestrian improvements will be a requirement of this role.
Trees
Knowledge and experience with tree maintenance and preservation specialty.
Must have experience with driving or operating specialized equipment (hydraulic lift and bucket, stump-grinder, verity of chain-saws, hand-pruners etc.)
Management and supervision (safety awareness, assessing tree damaged condition along streets and park grounds, receives and reviews requests for tree services, etc.),
Recommends the removal or pruning of existing trees;
Reviews construction plans and makes recommendations to preserve existing trees within the city’s right-of-way.
Must remove fallen and standing trees from city streets or park areas; trim branches from trees in order to preserve pedestrian and motorist visibility of street signs, stop signs and traffic lights; rigs, cuts, and removes dead or diseased tree members employing slings and ropes.
Basic computer literacy (ability to compose an e-mail, provide updates in simple report form, interact with timekeeping and asset management software, etc.)
Ability to communicate effectively with internal and external customers (written and oral).
Must be prepared to learn and adapt as new tools, processes, and practices become available.
Must be able to aid in the development of less experienced personnel through coaching and training (under the guidance of superintendent or designee).
As part of an emergency response unit, must be able to handle a rapid change of direction associated with environmental conditions.
Minimum Education & Experience
Graduation from an accredited high school or posses

Work arrangement
No