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 Indiana

168 results
Indianapolis, IN
2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Todd Castor Cars

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

77,934 miles

$30,533

Fair Deal
Muncie, IN
49 mi away
Year:
2019
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:
Automatic
Mileage:
77,934
Stock number:
K25087
VIN:
1GCPYCEF7KZ323403

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

10,114 miles

$44,500

Fair Deal
McCordsville, IN
16 mi away
Year:
2024
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:
10,114
Stock number:
2550
VIN:
3GCUDCED5RG448309

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

90,121 miles

$30,143

Fair Deal
Martinsville, IN
29 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:
Northsky Blue Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
90,121
Stock number:
A13A
VIN:
1GCPYCEF6MZ234845

Sponsored

2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

12,076 miles

$41,041

Good Deal
Plainfield, IN
13 mi away
Year:
2023
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:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
12,076
Stock number:
16186
VIN:
3GCUDCED3PG330210

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

72,460 miles

$27,681

Good Deal
Noblesville, IN
20 mi away
Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
4.3L V6 Flex Fuel Vehicle
Exterior color:
Northsky Blue Metallic
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
72,460
Stock number:
213089
VIN:
1GCPYCEHXLZ213089

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

73,120 miles

$30,462

Good Deal
Fishers, IN
16 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:
Northsky Blue Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
73,120
Stock number:
NTS11155A
VIN:
1GCPYCEF3MZ219414

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

173,569 miles

$20,988

Fair Deal
Indianapolis, IN
9 mi away
Year:
2019
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:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
173,569
Stock number:
T60257A
VIN:
1GCPYCEF6KZ397718

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

20,672 miles

$38,996

Fair Deal
Certified Pre-Owned
Daleville, IN
41 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:
Glacier Blue Metallic
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
20,672
Stock number:
A8869
VIN:
3GCPDCEK3PG129581

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

13,726 miles

$43,948

Fair Deal
McCordsville, IN
16 mi away
Year:
2024
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:
13,726
Stock number:
2597A
VIN:
3GCUDCED6RG445581

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

75,983 miles

$29,669

Good Deal
Plainfield, IN
11 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:
Cherry Red Tintcoat
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
75,983
Stock number:
T60478A
VIN:
1GCPYCEF2MZ364900

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

13,726 miles

$43,948

Fair Deal
McCordsville, IN
16 mi away
Year:
2024
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:
13,726
Stock number:
2597A
VIN:
3GCUDCED6RG445581

Sponsored

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

  • Chevrolet Silverado 1500 LT in Indiana

  • Chevrolet Silverado 1500 RST in Indiana

  • Chevrolet Silverado 1500 LTZ in Indiana

  • Chevrolet Silverado 1500 LT Trail Boss in Indiana

  • Chevrolet Silverado 1500 LT1 in Indiana

  • Chevrolet Silverado 1500 Custom in Indiana

  • Chevrolet Silverado 1500 High Country in Indiana

  • Chevrolet Silverado 1500 Custom Trail Boss in Indiana

  • Chevrolet Silverado 1500 Work Truck in Indiana

  • Chevrolet Silverado 1500 in Indianapolis IN

  • Chevrolet Silverado 1500 in Anderson IN

  • Chevrolet Silverado 1500 in Columbus IN

  • Chevrolet Silverado 1500 in Crawfordsville IN

  • Chevrolet Silverado 1500 in Bloomington IN

  • Chevrolet Silverado 1500 in Kokomo IN

  • Chevrolet Silverado 1500 in Lafayette IN

  • Chevrolet Silverado 1500 in Terre Haute IN

  • Chevrolet Silverado 1500 in Jasper IN

  • Chevrolet Silverado 1500 in Indiana

  • Old Chevy Trucks for Sale in Indiana

  • Classic Muscle Cars for Sale in Indiana

  • Chevrolet Trucks For Sale in Indiana

  • Cheap Muscle Cars for Sale in Indiana

  • Work Trucks for Sale in Indiana

  • Reliable Cars For Sale in Indiana

  • American Made Trucks For Sale in Indiana

  • Best Pickup Trucks For Sale in Indiana

  • Best Cars Under $5,000 For Sale in Indiana

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Indiana

  • 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

  • Champion Chevrolet

  • Sam Pierce Chevrolet

  • Stanley Chevrolet, Inc.

  • Dellen Chevrolet Buick GMC

  • Curry Auto Center

  • Greg Hubler Chevrolet

  • Hobson Chevrolet Buick GMC

  • Ray Skillman Chevrolet

  • Community Chevrolet of Spencer

  • Dan Young Chevrolet GMC

  • York Chevrolet Buick GMC Truck

  • Hubler Chevrolet Center

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.