Delivery Driver Jobs in Winterset, IA — Immediate Openings

As of April 2026, there are 30 delivery driver openings in Winterset, IA. Local pay ranges from $896 to $8,500/year. Listings are updated daily — benefits start Day 1 for most positions.

Grubhub

Grubhub Large Order Delivery Driver

Winterset, IA

$3,780 - $6,480

United Parcel Service (UPS)

UPS Package Delivery Driver(Logistics And Transportation)Vacancy in

Winterset, IA

$4,000 - $7,500

Midnight Logistics

(Winterset)Part-Time:Late Night Convenience & Grocery Courier

Winterset, IA

$2,800 - $4,800

Heavy Freight Logistics

Independent Contractor Driver-Cargo Van / Box Truck

Winterset, IA

$5,000 - $8,500

FreshDrop Logistics

Winterset Needs:Driver Opportunity(Part-Time)

Winterset, IA

$3,000 - $5,500

Urban Pedal Logistics

Start ASAP:Courier(Winterset)

Winterset, IA

$2,500 - $4,500

Suburban Delivery Network

Hiring in Winterset:Driver Opportunity(Part-Time)

Winterset, IA

$2,800 - $4,800

Secure Document Couriers

Independent Contractor Driver-Night Shift Legal/document

Winterset, IA

$2,800 - $5,000

Grubhub

Night Shift Grubhub Courier

Winterset, IA

$3,080 - $5,280

Urban Pedal Logistics

Urgent Hire in Winterset:Independent Contractor Driver-Urban

Winterset, IA

$2,500 - $4,500

Auto Logistics Pros

Winterset Independent Contractor Driver-Auto Parts Courier

Winterset, IA

$2,800 - $4,800

Final Mile Delivery Co.

$3k-$5.5k/Month Independent Contractor Driver-Final Mile Parcel job in

Winterset, IA

$3,000 - $5,500

Delivery Driver Jobs in Winterset — FAQ

How many delivery driver jobs are open in Winterset, IA?
There are currently 30+ delivery driver positions in Winterset, IA. New delivery driver roles are added regularly — check this page for the latest openings.
How much do delivery driver jobs pay in Winterset?
Delivery Driver pay in Winterset 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 delivery driver jobs in Winterset require experience?
Many delivery driver positions in Winterset 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 delivery driver jobs in Winterset?
Browse the 30+ delivery 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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Last updated: April 26, 2026