Cdl Driver Jobs in Winchester, KY — Open Positions

As of May 2026, there are 34 cdl driver openings in Winchester, KY. Local pay ranges from $18 to $130,000/year. Listings are updated daily — benefits start Day 1 for most positions.

Coach USA

Charter Bus Driver-CDL B With Passenger Endorsement-Winchester,KY

Winchester, KY

$20 - $29

Granite Construction

Winchester,KY:CDL B Water Truck Driver-Construction Site Dust Control

Winchester, KY

$26 - $32

Clean Harbors

Clean Harbors is hiring a CDL B Vacuum Truck Driver-Industrial

Winchester, KY

$26 - $35

Coach USA

Coach USA seeks Charter Bus Driver-CDL B With Passenger Endorsement in

Winchester, IL

$19 - $28

Matheson Postal Services

Winchester USPS Mail Haul Truck Driver-CDL A

Winchester, IL

$73,500 - $94,500

Foremost Transport

Mobile Home Transport Driver-CDL A Oversize

Winchester, IL

$90,000 - $120,000

First Student

Winchester-based School Bus Driver-CDL B With Passenger And S

Winchester, ID

$18 - $25

Hot Shot Transportation Co.

IL Career:Hot Shot Truck Driver-Owner Operator With 1 Ton Pickup in

Winchester, IL

$85,000 - $130,000

Clean Harbors

Winchester,IL:CDL B Vacuum Truck Driver-Industrial Cleaning at Clean

Winchester, IL

$25 - $34

Foremost Transport

Apply Now:Mobile Home Transport Driver-CDL A Oversize Load in

Winchester, KY

$90,000 - $120,000

Matheson Postal Services

Winchester:USPS Mail Haul Truck Driver-CDL A Contractor

Winchester, KY

$70,000 - $90,000

Matheson Postal Services

Winchester USPS Mail Haul Truck Driver-CDL A Contractor with

Winchester, NV

$77,000 - $99,000

Cdl Driver Jobs in Winchester — FAQ

How many cdl driver jobs are open in Winchester, KY?
There are currently 34+ cdl driver positions in Winchester, KY. New cdl driver roles are added regularly — check this page for the latest openings.
How much do cdl driver jobs pay in Winchester?
Cdl Driver pay in Winchester 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 Winchester require experience?
Many cdl driver positions in Winchester 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 Winchester?
Browse the 34+ 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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Other Driving Jobs in Winchester

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116 open positions

Other Driving Jobs in Winchester

5 open positions

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4 open positions

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1 open positions

Last updated: May 13, 2026