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 Pilgrim, KY

201 results
Pilgrim, KY
2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Barry's Chevrolet,Incorporated

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

39,673 miles

$36,000

Good Deal
West Union, OH
93 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:
39,673
Stock number:
GP599093
VIN:
3GCPDCED7NG599093

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

90,664 miles

$31,880

Fair Deal
Wytheville, VA
95 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
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
90,664
Stock number:
135072A
VIN:
1GCPYCEF7MZ442975

Sponsored

2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

133,523 miles

$27,978

Fair Deal
Bristol, TN
81 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:
Sterling Gray Metallic
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
133,523
Stock number:
364621A
VIN:
3GCPDCEK7PG203892

Sponsored

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

75,180 miles

$31,222

Fair Deal
Princeton, WV
80 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:
Red Hot
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
75,180
Stock number:
26370A
VIN:
3GCPYCEF0LG442055

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

84,951 miles

$28,994

Fair Deal
Richmond, KY
97 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:
Red Hot
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
84,951
Stock number:
372664
VIN:
1GCPYCEF3LZ372664

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Kentucky
  6. / Pilgrim
  • Chevrolet Silverado 1500 LT in Pilgrim KY

  • Chevrolet Silverado 1500 RST in Pilgrim KY

  • Chevrolet Silverado 1500 LTZ in Pilgrim KY

  • Chevrolet Silverado 1500 LT Trail Boss in Pilgrim KY

  • Chevrolet Silverado 1500 LT1 in Pilgrim KY

  • Chevrolet Silverado 1500 High Country in Pilgrim KY

  • Chevrolet Silverado 1500 Custom in Pilgrim KY

  • Chevrolet Silverado 1500 Custom Trail Boss in Pilgrim KY

  • Chevrolet Silverado 1500 Work Truck in Pilgrim KY

  • Chevrolet Silverado 1500 in Huntington WV

  • Chevrolet Silverado 1500 in Charleston WV

  • Chevrolet Silverado 1500 in Abingdon VA

  • Chevrolet Silverado 1500 in London KY

  • Chevrolet Silverado 1500 in Johnson City TN

  • Chevrolet Silverado 1500 in Greeneville TN

  • Chevrolet Silverado 1500 in Lexington KY

  • Chevrolet Silverado 1500 in Morristown TN

  • Chevrolet Silverado 1500 in Parkersburg WV

  • Chevrolet Silverado 1500 in Pilgrim KY

  • Old Chevy Trucks for Sale in Pilgrim KY

  • Classic Muscle Cars for Sale in Pilgrim KY

  • Chevrolet Trucks For Sale in Pilgrim KY

  • Cheap Muscle Cars for Sale in Pilgrim KY

  • Work Trucks for Sale in Pilgrim KY

  • Reliable Cars For Sale in Pilgrim KY

  • American Made Trucks For Sale in Pilgrim KY

  • Best Pickup Trucks For Sale in Pilgrim KY

  • Best Cars Under $5,000 For Sale in Pilgrim KY

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Pilgrim KY

  • 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

  • Dutch Miller Chevrolet

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.