Delivery Driver Jobs in Winterset, IA — Now Hiring

As of May 2026, there are 39 delivery driver openings in Winterset, IA. Local pay ranges from $14 to $151,200/year. Listings are updated daily — benefits start Day 1 for most positions.

United Parcel Service (UPS)

Winterset UPS Package Delivery Driver(Full-time)-United Parcel Service

Winterset, IA

$4,000 - $7,500

FedEx Ground

Winterset Full-time Opening:Delivery Driver-Package Handler | Hiring

Winterset, IA

$21 - $26

FedEx Custom Critical

Winterset Expedited Sprinter Van Driver-Time Critical Cargo

Winterset, IA

$84,000 - $151,200

DoorDash

Doordash(Winterset)Hiring:Morning Shift Delivery Driver | Apply Now

Winterset, IA

$2,970 - $5,060

Corporate Catering Couriers

$3.5k-$6k/Month Independent Contractor Driver-Catering Logistics job

Winterset, IA

$3,500 - $6,000

Uber Eats

Work in Winterset:Alcohol Delivery Driver | Hiring

Winterset, IA

$3,000 - $5,000

Heavy Freight Logistics

Winterset Independent Contractor Driver-Cargo Van / Box Truck

Winterset, IA

$5,000 - $8,500

XPO Logistics

Winterset Delivery Driver-Package Handler Box Truck with $22-$28/hr

Winterset, IA

$22 - $28

Roadie

$4.8k-$8.3k/Month Big & Bulky Delivery Driver job in Winterset

Winterset, IA

$4,830 - $8,280

Urban Pedal Logistics

Join Team in Winterset:Independent Contractor Driver-Urban

Winterset, IA

$2,500 - $4,500

Shipt

Pharmacy Delivery Driver-Winterset,IA | Hiring

Winterset, IA

$3,472 - $5,824

Grubhub

Work in Winterset:Suburban Delivery Driver | Hiring

Winterset, IA

$3,000 - $4,900

Delivery Driver Jobs in Winterset — FAQ

How many delivery driver jobs are open in Winterset, IA?
There are currently 39+ 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 39+ 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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Other Driving Jobs in Winterset

Cdl Driver Jobs in Winterset

9 open positions

Warehouse Jobs in Winterset

1 open positions

Yard Jockey Jobs in Winterset

1 open positions

Last updated: May 14, 2026