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 Dema, KY

201 results
Lackey, KY
2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Crossroads Chevrolet

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

33,593 miles

$39,920

Fair Deal
Mount Hope, WV
94 mi away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Summit White
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
33,593
Stock number:
RG231181
VIN:
3GCPDCEK0RG231181

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

69,518 miles

$28,985

Great Deal
Nicholasville, KY
100 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Northsky Blue Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
69,518
Stock number:
NG192327
VIN:
3GCPYCEK5NG192327

Sponsored

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

92,000 miles

$29,419

Fair Deal
Pikeville, KY
13 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:
Northsky Blue Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
92,000
Stock number:
P7788A
VIN:
1GCPYCEF5LZ206520

Sponsored

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,295 miles

$32,547

Good Deal
Store transfer to Bristol, TN
855 mi away • Price includes $549 shipping Price includes $549 shipping
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Black
Interior color:
Black
Transmission:
Automatic
Mileage:
59,295
Stock number:
27914192
VIN:
3GCPYCEK6NG133965

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

4,502 miles

$41,889

Good Deal
Certified Pre-Owned
Morristown, TN
90 mi away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Black
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
4,502
Stock number:
18765A
VIN:
3GCPDCEK1RG354732

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
95 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

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

23,865 miles

$38,401

Good Deal
Lexington, KY
99 mi away
Year:
2024
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
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
23,865
Stock number:
N8897
VIN:
3GCPDCEK7RG398038

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

8,237 miles

$45,815

Good Deal
Middlesboro, KY
76 mi away
Year:
2025
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
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
8,237
Stock number:
P1059M
VIN:
3GCUKCED8SG149893

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

69,518 miles

$28,985

Great Deal
Nicholasville, KY
100 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Northsky Blue Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
69,518
Stock number:
NG192327
VIN:
3GCPYCEK5NG192327

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

92,000 miles

$29,419

Fair Deal
Pikeville, KY
13 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:
Northsky Blue Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
92,000
Stock number:
P7788A
VIN:
1GCPYCEF5LZ206520

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

96,335 miles

$29,888

Fair Deal
Richmond, KY
81 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:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
96,335
Stock number:
376644
VIN:
1GCPYCEF4MZ376644

Sponsored

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

  • Chevrolet Silverado 1500 RST in Dema KY

  • Chevrolet Silverado 1500 LTZ in Dema KY

  • Chevrolet Silverado 1500 LT Trail Boss in Dema KY

  • Chevrolet Silverado 1500 LT1 in Dema KY

  • Chevrolet Silverado 1500 High Country in Dema KY

  • Chevrolet Silverado 1500 Custom in Dema KY

  • Chevrolet Silverado 1500 Custom Trail Boss in Dema KY

  • Chevrolet Silverado 1500 Work Truck in Dema KY

  • Chevrolet Silverado 1500 in Huntington 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 Morristown TN

  • Chevrolet Silverado 1500 in Charleston WV

  • Chevrolet Silverado 1500 in Lexington KY

  • Chevrolet Silverado 1500 in Knoxville TN

  • Chevrolet Silverado 1500 in Dema KY

  • Old Chevy Trucks for Sale in Dema KY

  • Classic Muscle Cars for Sale in Dema KY

  • Chevrolet Trucks For Sale in Dema KY

  • Cheap Muscle Cars for Sale in Dema KY

  • Work Trucks for Sale in Dema KY

  • Reliable Cars For Sale in Dema KY

  • American Made Trucks For Sale in Dema KY

  • Best Pickup Trucks For Sale in Dema KY

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

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Dema 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

  • Morgan McClure Chevrolet

  • Freedom 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.