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 LT Trail Boss for Sale near Wellington, KY

375 results
Wellington, KY
2025 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD Tom Gill Chevrolet

2025 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

8,232 miles

$46,294

Great Deal
Florence, KY
97 mi away
Year:
2025
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:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
8,232
Stock number:
36859A
VIN:
3GCPKFEK3SG306887

Sponsored

2020 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

142,365 miles

$22,388

Great Deal
Grayson, KY
41 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
Fuel type:
Gasoline
Mileage:
142,365
Stock number:
225432
VIN:
3GCPYFED4LG225432

Sponsored

2020 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

136,838 miles

$25,500

Good Deal
Maysville, KY
51 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:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
136,838
Stock number:
T371587
VIN:
1GCPYFED6LZ371587

Sponsored

2020 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

107,322 miles

$29,777

Great Deal
Big Stone Gap, VA
86 mi away
Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Cajun Red Tintcoat
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
107,322
Stock number:
AM0483
VIN:
1GCPYFEL5LZ270483

2024 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

14,127 miles

$48,990

Great Deal
Richmond, KY
44 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:
14,127
Stock number:
297128
VIN:
3GCUDFEDXRG297128

2020 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

142,365 miles

$22,388

Great Deal
Grayson, KY
41 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
Fuel type:
Gasoline
Mileage:
142,365
Stock number:
225432
VIN:
3GCPYFED4LG225432

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

29,492 miles

$39,588

Good Deal
Barboursville, WV
75 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:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
29,492
Stock number:
88E12069
VIN:
3GCPYFED5MG376863

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

63,466 miles

$36,915

Good Deal
Nicholasville, KY
58 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Gray (Satin Steel Metallic)
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
63,466
Stock number:
NG120181
VIN:
3GCPYFED2NG120181

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

106,227 miles

$27,700

Good Deal
Lexington, KY
53 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:
Silver Ice Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
106,227
Stock number:
L0755A
VIN:
3GCPYFED5KG120574

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

15,982 miles

$49,258

Great Deal
Cincinnati, OH
90 mi away
Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Gray
Combined gas mileage:
23 MPG
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
15,982
Stock number:
PT-22584A
VIN:
3GCUKFE82SG154432

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

79,613 miles

$31,397

Great Deal
Morehead, KY
17 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:
Blue Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
79,613
Stock number:
K012P
VIN:
1GCPYFED7LZ358816

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

55,971 miles

$40,750

Good Deal
Hurricane, WV
86 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
Combined gas mileage:
24 MPG
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
55,971
Stock number:
9534A
VIN:
3GCUDFET7NG624358

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

69,167 miles

$33,764

Great Deal
Morehead, KY
17 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:
Silver Ice Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
69,167
Stock number:
K038P
VIN:
3GCPYFED1MG431776

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

37,929 miles

$40,950

Fair Deal
Pikeville, KY
62 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Glacier Blue Metallic
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
37,929
Stock number:
FST229
VIN:
3GCUDFED2NG690812

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

8,582 miles

$56,322

Good Deal
Cincinnati, OH
97 mi away
Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Black
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
8,582
Stock number:
1023643
VIN:
3GCUKFEL9SG201119

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / LT Trail Boss
  5. / Kentucky
  6. / Wellington

  • Chevrolet Silverado 1500 LT in Wellington KY

  • Chevrolet Silverado 1500 RST in Wellington KY

  • Chevrolet Silverado 1500 LTZ in Wellington KY

  • Chevrolet Silverado 1500 LT Trail Boss in Wellington KY

  • Chevrolet Silverado 1500 LT1 in Wellington KY

  • Chevrolet Silverado 1500 Custom in Wellington KY

  • Chevrolet Silverado 1500 High Country in Wellington KY

  • Chevrolet Silverado 1500 Custom Trail Boss in Wellington KY

  • Chevrolet Silverado 1500 Work Truck in Wellington KY

  • Chevrolet Silverado 1500 in Lexington KY

  • Chevrolet Silverado 1500 in London KY

  • Chevrolet Silverado 1500 in Huntington WV

  • Chevrolet Silverado 1500 in Cincinnati OH

  • Chevrolet Silverado 1500 in Charleston WV

  • Chevrolet Silverado 1500 in Abingdon VA

  • Chevrolet Silverado 1500 in Morristown TN

  • Chevrolet Silverado 1500 in Louisville KY

  • Chevrolet Silverado 1500 in Greeneville TN

  • Chevrolet Silverado 1500 in Wellington KY

  • Old Chevy Trucks for Sale in Wellington KY

  • Classic Muscle Cars for Sale in Wellington KY

  • Chevrolet Trucks For Sale in Wellington KY

  • Cheap Muscle Cars for Sale in Wellington KY

  • Work Trucks for Sale in Wellington KY

  • Reliable Cars For Sale in Wellington KY

  • American Made Trucks For Sale in Wellington KY

  • Best Pickup Trucks For Sale in Wellington KY

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

  • 2019 Chevrolet Silverado 1500 LT Trail Boss in Wellington 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

  • Dan Cummins Chevrolet Buick

  • Dutch's Chevrolet

  • Eagle 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

© 2026 CarGurus, Inc., All Rights Reserved.