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 Woolwine, VA

188 results
Woolwine, VA
2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Smart Cars By Wieland

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

100,480 miles

$25,998

Good Deal
Pittsboro, NC
96 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:
Gray
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
100,480
Stock number:
11519
VIN:
1GCPYCEFXKZ249992

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

66,301 miles

$34,245

Good Deal
Certified Pre-Owned
Hickory, NC
96 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:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
66,301
Stock number:
0H2182
VIN:
3GCPDCED9NG638170

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

1,339 miles

$44,388

Fair Deal
Kannapolis, NC
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:
Dark Ash Metallic
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
1,339
Stock number:
K2131A
VIN:
3GCPDCEK4RG397672

Sponsored

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

7,270 miles

$44,997

Good Deal
Mount Airy, NC
29 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:
Slate Gray Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
7,270
Stock number:
C4063B
VIN:
3GCUKCED6SG199871

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

75,857 miles

$32,991

Fair Deal
Certified Pre-Owned
Greensboro, NC
56 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:
75,857
Stock number:
K23681
VIN:
1GCPYCEF8MZ174177

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

100,480 miles

$25,998

Good Deal
Pittsboro, NC
96 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:
Gray
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
100,480
Stock number:
11519
VIN:
1GCPYCEFXKZ249992

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

1,339 miles

$44,388

Fair Deal
Kannapolis, NC
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:
Dark Ash Metallic
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
1,339
Stock number:
K2131A
VIN:
3GCPDCEK4RG397672

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

3,504 miles

$39,897

Great Deal
Mount Airy, NC
29 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:
3,504
Stock number:
C3891A
VIN:
3GCPDCEK5RG264449

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

31,336 miles

$37,999

Fair Deal
Princeton, WV
60 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
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
31,336
Stock number:
26657A
VIN:
3GCPYCEF6MG351812

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Virginia
  6. / Woolwine
  • Chevrolet Silverado 1500 LT in Woolwine VA

  • Chevrolet Silverado 1500 RST in Woolwine VA

  • Chevrolet Silverado 1500 LTZ in Woolwine VA

  • Chevrolet Silverado 1500 LT Trail Boss in Woolwine VA

  • Chevrolet Silverado 1500 LT1 in Woolwine VA

  • Chevrolet Silverado 1500 High Country in Woolwine VA

  • Chevrolet Silverado 1500 Custom in Woolwine VA

  • Chevrolet Silverado 1500 Custom Trail Boss in Woolwine VA

  • Chevrolet Silverado 1500 Work Truck in Woolwine VA

  • Chevrolet Silverado 1500 in Martinsville VA

  • Chevrolet Silverado 1500 in Blacksburg VA

  • Chevrolet Silverado 1500 in Roanoke VA

  • Chevrolet Silverado 1500 in Winston Salem NC

  • Chevrolet Silverado 1500 in Danville VA

  • Chevrolet Silverado 1500 in Greensboro NC

  • Chevrolet Silverado 1500 in Lynchburg VA

  • Chevrolet Silverado 1500 in Salisbury NC

  • Chevrolet Silverado 1500 in Hickory NC

  • Chevrolet Silverado 1500 in Woolwine VA

  • Old Chevy Trucks for Sale in Woolwine VA

  • Classic Muscle Cars for Sale in Woolwine VA

  • Chevrolet Trucks For Sale in Woolwine VA

  • Cheap Muscle Cars for Sale in Woolwine VA

  • Work Trucks for Sale in Woolwine VA

  • Reliable Cars For Sale in Woolwine VA

  • American Made Trucks For Sale in Woolwine VA

  • Best Pickup Trucks For Sale in Woolwine VA

  • Best Cars Under $5,000 For Sale in Woolwine VA

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Woolwine VA

  • 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

  • Aschenbach Chevrolet GMC

  • Pinkerton Chevrolet

  • Johnson Family Chevrolet

  • GR 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.