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 Winston Salem, NC

194 results
Winston Salem, NC
2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Jerry Hunt SuperCenter

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

5,767 miles

$44,939

Good Deal
Lexington, NC
18 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:
Slate Gray Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
5,767
Stock number:
25568
VIN:
3GCUDCEDXRG413281

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

115,912 miles

$27,288

Fair Deal
Charlotte, NC
70 mi away
Year:
2021
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:
Summit White
Fuel type:
Flex Fuel Vehicle
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
115,912
Stock number:
248778
VIN:
1GCPYCEH8MZ248778

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

68,118 miles

$34,353

Fair Deal
Graham, NC
47 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:
68,118
Stock number:
252177B
VIN:
1GCPYCEF7MZ165504

Sponsored

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

5,263 miles

$43,995

Good Deal
Boone, NC
80 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:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
5,263
Stock number:
B00881
VIN:
3GCPKCEK3SG372757

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

48,692 miles

$39,238

Great Deal
Apex, NC
83 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:
Jet Black
Transmission:
Automatic
Mileage:
48,692
Stock number:
DS64047A
VIN:
3GCUDCED9RG153679

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

34,960 miles

$41,999

Good Deal
Newton, NC
63 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:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
34,960
Stock number:
S19242P
VIN:
3GCUDCEDXRG129312

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

5,767 miles

$44,939

Good Deal
Lexington, NC
18 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:
Slate Gray Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
5,767
Stock number:
25568
VIN:
3GCUDCEDXRG413281

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

15,803 miles

$42,990

Fair Deal
Shelby, NC
92 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:
Slate Gray Metallic
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
15,803
Stock number:
S926A
VIN:
3GCPDCEK4RG260361

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

130,689 miles

$24,990

Good Deal
Raleigh, NC
92 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:
White
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Transmission:
6-Speed Automatic Overdrive
Mileage:
130,689
Stock number:
D114408
VIN:
3GCPYCEF9MG114408

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

83,224 miles

$28,236

Fair Deal
Boone, NC
78 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:
Black
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
83,224
Stock number:
321111A
VIN:
1GCRYCEH1LZ321111

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / North Carolina
  6. / Winston Salem
  • Chevrolet Silverado 1500 LT in Winston Salem NC

  • Chevrolet Silverado 1500 RST in Winston Salem NC

  • Chevrolet Silverado 1500 LTZ in Winston Salem NC

  • Chevrolet Silverado 1500 LT Trail Boss in Winston Salem NC

  • Chevrolet Silverado 1500 LT1 in Winston Salem NC

  • Chevrolet Silverado 1500 High Country in Winston Salem NC

  • Chevrolet Silverado 1500 Custom in Winston Salem NC

  • Chevrolet Silverado 1500 Custom Trail Boss in Winston Salem NC

  • Chevrolet Silverado 1500 Work Truck in Winston Salem NC

  • Chevrolet Silverado 1500 in Greensboro NC

  • Chevrolet Silverado 1500 in Salisbury NC

  • Chevrolet Silverado 1500 in Martinsville VA

  • Chevrolet Silverado 1500 in Danville VA

  • Chevrolet Silverado 1500 in Hickory NC

  • Chevrolet Silverado 1500 in Charlotte NC

  • Chevrolet Silverado 1500 in Sanford NC

  • Chevrolet Silverado 1500 in Blacksburg VA

  • Chevrolet Silverado 1500 in Roanoke VA

  • Chevrolet Silverado 1500 in Winston Salem NC

  • Old Chevy Trucks for Sale in Winston Salem NC

  • Classic Muscle Cars for Sale in Winston Salem NC

  • Chevrolet Trucks For Sale in Winston Salem NC

  • Cheap Muscle Cars for Sale in Winston Salem NC

  • Work Trucks for Sale in Winston Salem NC

  • Reliable Cars For Sale in Winston Salem NC

  • American Made Trucks For Sale in Winston Salem NC

  • Best Pickup Trucks For Sale in Winston Salem NC

  • Best Cars Under $5,000 For Sale in Winston Salem NC

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Winston Salem NC

  • 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

  • Impex Chevrolet GMC

  • Flow GM Auto Center of Winston Salem

  • Bill Black Chevrolet Cadillac

  • Team Chevrolet Buick GMC Cadillac

  • Vann York's GM Auto Park

  • Tim Marburger Chevrolet

  • Capital Chevrolet Buick GMC

  • GR Chevrolet GMC

  • Scenic Automotive

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

© 2025 CarGurus, Inc., All Rights Reserved.