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 Medora, IN

175 results
Medora, IN
2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

69,348 miles

$34,295

Good Deal
Salem, IN
19 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
277 hp 3L I6 Diesel
Exterior color:
Sand Dune Metallic
Fuel type:
Diesel
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
69,348
Stock number:
S11001T-1
VIN:
3GCUDCET9NG555963

Sponsored

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

54,657 miles

$32,999

Fair Deal
Bloomington, IN
27 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:
Shadow Gray Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
54,657
Stock number:
368823A
VIN:
1GCPYCEF5LZ127851

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

137,393 miles

$19,999

Great Deal
Bedford, IN
17 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:
Cajun Red Tintcoat
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
137,393
Stock number:
FP565A
VIN:
1GCPYCEF2KZ352064

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

57,665 miles

$32,900

Fair Deal
North Vernon, IN
32 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Black
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
57,665
Stock number:
P5513c
VIN:
1GCPYCEK3NZ142882

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

137,393 miles

$19,999

Great Deal
Bedford, IN
17 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:
Cajun Red Tintcoat
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
137,393
Stock number:
FP565A
VIN:
1GCPYCEF2KZ352064

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

54,657 miles

$32,999

Fair Deal
Bloomington, IN
27 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:
Shadow Gray Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
54,657
Stock number:
368823A
VIN:
1GCPYCEF5LZ127851

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

69,348 miles

$34,295

Good Deal
Salem, IN
19 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
277 hp 3L I6 Diesel
Exterior color:
Sand Dune Metallic
Fuel type:
Diesel
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
69,348
Stock number:
S11001T-1
VIN:
3GCUDCET9NG555963

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

  • Chevrolet Silverado 1500 RST in Medora IN

  • Chevrolet Silverado 1500 LTZ in Medora IN

  • Chevrolet Silverado 1500 LT Trail Boss in Medora IN

  • Chevrolet Silverado 1500 LT1 in Medora IN

  • Chevrolet Silverado 1500 High Country in Medora IN

  • Chevrolet Silverado 1500 Custom in Medora IN

  • Chevrolet Silverado 1500 Custom Trail Boss in Medora IN

  • Chevrolet Silverado 1500 Work Truck in Medora IN

  • Chevrolet Silverado 1500 in Bloomington IN

  • Chevrolet Silverado 1500 in Columbus IN

  • Chevrolet Silverado 1500 in Louisville KY

  • Chevrolet Silverado 1500 in Jasper IN

  • Chevrolet Silverado 1500 in Indianapolis IN

  • Chevrolet Silverado 1500 in Terre Haute IN

  • Chevrolet Silverado 1500 in Owensboro KY

  • Chevrolet Silverado 1500 in Cincinnati OH

  • Chevrolet Silverado 1500 in Anderson IN

  • Chevrolet Silverado 1500 in Medora IN

  • Old Chevy Trucks for Sale in Medora IN

  • Classic Muscle Cars for Sale in Medora IN

  • Chevrolet Trucks For Sale in Medora IN

  • Cheap Muscle Cars for Sale in Medora IN

  • Work Trucks for Sale in Medora IN

  • Reliable Cars For Sale in Medora IN

  • American Made Trucks For Sale in Medora IN

  • Best Pickup Trucks For Sale in Medora IN

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

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Medora 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

  • John Jones of Corydon

  • John Jones Chevrolet Cadillac of Salem

  • Hobson Chevrolet Buick GMC

  • John Jones Chevrolet of Scottsburg

  • Curry Auto Center

  • Hubler Chevrolet Buick GMC Bedford

  • Community Chevrolet of Spencer

  • Country Chevrolet Buick

  • Bob Poynter Chevrolet Buick 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

© 2026 CarGurus, Inc., All Rights Reserved.