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 Chesterton, IN

145 results
Chesterton, IN
2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Garber Chevrolet Highland

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

34,986 miles

$39,975

Fair Deal
Certified Pre-Owned
Highland, IN
23 mi away
Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Red
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
34,986
Stock number:
21100975P
VIN:
3GCPDCEK0PG100975

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,336 miles

$32,533

Good Deal
Michigan City, IN
8 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:
Summit White
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
55,336
Stock number:
35-26090A
VIN:
1GCPYCEF4MZ280626

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

98,227 miles

$29,521

Fair Deal
Certified Pre-Owned
Frankfort, IL
43 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:
Gray (Satin Steel Metallic)
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
98,227
Stock number:
60969A
VIN:
1GCPYCEF5MZ291179

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,336 miles

$32,533

Good Deal
Michigan City, IN
8 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:
Summit White
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
55,336
Stock number:
35-26090A
VIN:
1GCPYCEF4MZ280626

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

83,668 miles

$28,995

Good Deal
Certified Pre-Owned
Frankfort, IL
42 mi away
Year:
2020
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:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
83,668
Stock number:
48530
VIN:
3GCPYCEF1LG107936

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

118,420 miles

$26,395

Fair Deal
Certified Pre-Owned
Melrose Park, IL
47 mi away
Year:
2020
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 (Satin Steel Metallic)
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
118,420
Stock number:
60890A
VIN:
1GCPYCEF4LZ171792

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

27,989 miles

$39,794

Fair Deal
Certified Pre-Owned
Riverside, IL
43 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:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
27,989
Stock number:
Z5195
VIN:
3GCPYCEL8NG176342

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Indiana
  6. / Chesterton
  • Chevrolet Silverado 1500 LT in Chesterton IN

  • Chevrolet Silverado 1500 RST in Chesterton IN

  • Chevrolet Silverado 1500 LTZ in Chesterton IN

  • Chevrolet Silverado 1500 LT Trail Boss in Chesterton IN

  • Chevrolet Silverado 1500 LT1 in Chesterton IN

  • Chevrolet Silverado 1500 Custom in Chesterton IN

  • Chevrolet Silverado 1500 High Country in Chesterton IN

  • Chevrolet Silverado 1500 Custom Trail Boss in Chesterton IN

  • Chevrolet Silverado 1500 Work Truck in Chesterton IN

  • Chevrolet Silverado 1500 in Chicago IL

  • Chevrolet Silverado 1500 in South Bend IN

  • Chevrolet Silverado 1500 in Palatine IL

  • Chevrolet Silverado 1500 in Aurora IL

  • Chevrolet Silverado 1500 in Kenosha WI

  • Chevrolet Silverado 1500 in Lafayette IN

  • Chevrolet Silverado 1500 in Kalamazoo MI

  • Chevrolet Silverado 1500 in Kokomo IN

  • Chevrolet Silverado 1500 in Holland MI

  • Chevrolet Silverado 1500 in Chesterton IN

  • Old Chevy Trucks for Sale in Chesterton IN

  • Classic Muscle Cars for Sale in Chesterton IN

  • Chevrolet Trucks For Sale in Chesterton IN

  • Cheap Muscle Cars for Sale in Chesterton IN

  • Work Trucks for Sale in Chesterton IN

  • Reliable Cars For Sale in Chesterton IN

  • American Made Trucks For Sale in Chesterton IN

  • Best Pickup Trucks For Sale in Chesterton IN

  • Best Cars Under $5,000 For Sale in Chesterton IN

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Chesterton IN

  • 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

  • Used SUVs / Crossovers for Sale with Low Mileage

  • Used Hatchbacks for Sale with Low Mileage

  • Used Convertibles for Sale with Low Mileage

  • Used Vans for Sale with Low Mileage

  • Used Minivans for Sale with Low Mileage

  • Used Pickup Trucks for Sale with Low Mileage

  • Used Coupes for Sale with Low Mileage

  • Used Wagons for Sale with Low Mileage

  • Advantage Chevrolet Hodgkins

  • Phillips Chevrolet of Frankfort

  • Chevrolet of Merrillville

  • Jennings Chevrolet

  • Phillips Chevrolet of Lansing

  • Garber Chevrolet Highland

  • Team Chevrolet

  • Route 1 Chevrolet

  • Graff Chevrolet GMC of Michigan City

  • Currie Motors Chevrolet

  • Apple Chevrolet

  • Wiers Chevrolet GMC

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

© 2025 CarGurus, Inc., All Rights Reserved.