Cdl Driver Jobs in Winter Haven, FL — Start This Week

As of October 2026, there are 58 cdl driver openings in Winter Haven, FL. Local pay ranges from $20 to $345,800/year. Listings are updated daily — benefits start Day 1 for most positions.

Granite Construction

CDL B Water Truck Driver - Construction Site Dust Control

Winter Haven, FL

$29 - $35

Performance Foodservice

Performance Foodservice seeks CDL Class A Route Delivery Driver in

Winter Haven, FL

$70,000 - $90,000

PepsiCo

Beverage Distribution Box Truck Driver(Gig)-Winter Haven

Winter Haven, FL

$5,000 - $7,500

Schneider National

CDL A Truck Driver - OTR Dry Van

Winter Haven, FL

$75,000 - $96,000

Foremost Transport

Mobile Home Transport Driver - CDL A Oversize Load

Winter Haven, FL

$97,200 - $129,600

J.B. Hunt Intermodal

CDL A Truck Driver - Intermodal Container Drayage

Winter Haven, FL

$66,000 - $83,600

General Beer Northeast

Beer Delivery Driver - CDL A Distributor Route

Winter Haven, FL

$22 - $29

Sysco

Evening Part-Time Foodservice Delivery Driver-CDL A Home Daily –

Winter Haven, FL

$74,800 - $92,400

Old Dominion Freight Line

Old Dominion Linehaul Driver

Winter Haven, FL

$8,049 - $11,500

Black Eagle Express

CDL A Truck Driver - OTR Flatbed Conestoga

Winter Haven, FL

$104,000 - $130,000

United States Postal Service

Recruiting:USPS Commercial Box Truck Driver

Winter Haven, FL

$4,500 - $6,500

Waste Management

CDL B Garbage Truck Driver - Residential Refuse

Winter Haven, FL

$26 - $34

Cdl Driver Jobs in Winter Haven — FAQ

How many cdl driver jobs are open in Winter Haven, FL?
There are currently 58+ cdl driver positions in Winter Haven, FL. New cdl driver roles are added regularly — check this page for the latest openings.
How much do cdl driver jobs pay in Winter Haven?
Cdl Driver pay in Winter Haven varies by employer, route type, and experience level. Many positions offer shift differentials, mileage bonuses, and sign-on bonuses. Browse the listings above to see pay details for each opening.
Do cdl driver jobs in Winter Haven require experience?
Many cdl driver positions in Winter Haven welcome entry-level applicants. Employers like Amazon, FedEx, and UPS often provide paid training. CDL positions may require a valid commercial license — check individual listings for specific requirements.
How do I apply for cdl driver jobs in Winter Haven?
Browse the 58+ cdl driver listings above, click on any position for full details including pay, schedule, and requirements, then follow the application link. Most driving positions have a simple online application.

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170 open positions

Other Driving Jobs in Winter Haven

8 open positions

DSP Driver Jobs in Winter Haven

6 open positions

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3 open positions

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2 open positions

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1 open positions

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1 open positions

Overnight Driving Jobs in Winter Haven

1 open positions

Last updated: October 03, 2026