CarGurus Logo Homepage Link
  • Buy
    • Used cars
    • New cars
    • Certified pre-owned
    • Start your purchase online
    • Dealerships near me
  • Sell
    • Sell my car
    • Car values
    • Sell my car FAQs
  • Finance
    • Prequalify for financing
    • How does it work?
    • Financing FAQs
  • Research
    • Test drive reviews
    • Price trends
    • Tips & advice
    • Electric cars
    • Compare cars
  • Discover
    The latest way to shop:
    smarter research, better
    listings.
  • Saved cars & searches
  • Sign in / Register
    • My account
    • Saved searches
    • Saved cars
    • Recommended cars
    • Browsing history
    • Financing dashboard
      • United States (EN)
      • Estados Unidos (ES)
      • Canada (EN)
      • Canada (FR)
      • United Kingdom

Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Simpson, IL

139 results
Simpson, IL
2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

80,732 miles

$32,800

Fair Deal
Certified Pre-Owned
Cape Girardeau, MO
45 mi away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Black
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
80,732
Stock number:
P4778
VIN:
1GCPYCEF4MZ451388

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

32,627 miles

$37,780

Good Deal
Germantown, IL
87 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Dark Ash Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
32,627
Stock number:
26233B
VIN:
3GCPDCED1NG676170

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

80,732 miles

$32,800

Fair Deal
Certified Pre-Owned
Cape Girardeau, MO
45 mi away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Black
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
80,732
Stock number:
P4778
VIN:
1GCPYCEF4MZ451388

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

8,200 miles

$48,245

Fair Deal
Princeton, IN
88 mi away
Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Gray
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
8,200
Stock number:
P08266A
VIN:
3GCUKCED2SG211398

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

37,678 miles

$34,900

Good Deal
Benton, MO
50 mi away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Black
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
37,678
Stock number:
196967
VIN:
1GCPYCEF4MZ196967

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Illinois
  6. / Simpson

  • Chevrolet Silverado 1500 LT in Simpson IL

  • Chevrolet Silverado 1500 RST in Simpson IL

  • Chevrolet Silverado 1500 LTZ in Simpson IL

  • Chevrolet Silverado 1500 LT Trail Boss in Simpson IL

  • Chevrolet Silverado 1500 LT1 in Simpson IL

  • Chevrolet Silverado 1500 Custom in Simpson IL

  • Chevrolet Silverado 1500 High Country in Simpson IL

  • Chevrolet Silverado 1500 Custom Trail Boss in Simpson IL

  • Chevrolet Silverado 1500 Work Truck in Simpson IL

  • Chevrolet Silverado 1500 in Paducah KY

  • Chevrolet Silverado 1500 in Carbondale IL

  • Chevrolet Silverado 1500 in Cape Girardeau MO

  • Chevrolet Silverado 1500 in Evansville IN

  • Chevrolet Silverado 1500 in Owensboro KY

  • Chevrolet Silverado 1500 in Clarksville TN

  • Chevrolet Silverado 1500 in Saint Louis MO

  • Chevrolet Silverado 1500 in Jasper IN

  • Chevrolet Silverado 1500 in Jackson TN

  • Chevrolet Silverado 1500 in Simpson IL

  • Old Chevy Trucks for Sale in Simpson IL

  • Classic Muscle Cars for Sale in Simpson IL

  • Chevrolet Trucks For Sale in Simpson IL

  • Cheap Muscle Cars for Sale in Simpson IL

  • Work Trucks for Sale in Simpson IL

  • Reliable Cars For Sale in Simpson IL

  • American Made Trucks For Sale in Simpson IL

  • Best Pickup Trucks For Sale in Simpson IL

  • Best Cars Under $5,000 For Sale in Simpson IL

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Simpson IL

  • All Used Cars

  • Manual Transmission Cars

  • Luxury Cars

  • Cars with Red Interior

  • Cheap Manual Cars

  • Hybrid Cars

  • Sports Cars

  • Electric SUVs

  • Cheap Trucks

  • Small Cars

  • Third Row SUVs

  • Three Quarter Ton Trucks

  • Lifted Trucks

  • Manual Transmission Trucks

  • Diesel Trucks

  • Hybrid SUVs

  • Dually Trucks

  • One Ton Trucks

  • Cheap SUVs

  • Lifted Ford Trucks

  • 4x4 Trucks

  • Work Trucks

  • AWD SUVs

  • Ford Trucks

  • Chevrolet Trucks

  • Toyota Trucks

  • Trucks Under $10,000

  • Cars Under $15,000

  • Sports Cars Under $20,000

  • Trucks Under $20,000

  • Used Sedans for Sale with Low Mileage in Simpson

  • Used SUVs / Crossovers for Sale with Low Mileage in Simpson

  • Used Hatchbacks for Sale with Low Mileage in Simpson

  • Used Convertibles for Sale with Low Mileage in Simpson

  • Used Vans for Sale with Low Mileage in Simpson

  • Used Minivans for Sale with Low Mileage in Simpson

  • Used Pickup Trucks for Sale with Low Mileage in Simpson

  • Used Coupes for Sale with Low Mileage in Simpson

  • Used Wagons for Sale with Low Mileage in Simpson

Connect with us
Download our app
Download on the App Store Get it on Google Play
  • Company
  • About CarGurus
  • Our team
  • Press
  • Investor relations
  • Price trends
  • Careers
  • Advertise with CarGurus
  • For dealers
  • Dealer signup
  • Dealer resources
  • Terms
  • Terms of use
  • Privacy policy
  • Interest-based ads
  • Security
  • Help
  • Help center
  • Contact us
Click for the BBB Business Review of this Auto Listing Service in Cambridge MA
    • United States (EN)
    • Estados Unidos (ES)
    • Canada (EN)
    • Canada (FR)
    • United Kingdom

© 2026 CarGurus, Inc., All Rights Reserved.