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 Williamsburg, VA

272 results
Williamsburg, VA
2025 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD CMA's Colonial Chevrolet

2025 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

14,913 miles

$52,810

Good Deal
Chester, VA
39 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:
Radiant Red Tintcoat
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
14,913
Stock number:
C7213A
VIN:
3GCUKFEDXSG108828

Sponsored

2019 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

39,495 miles

$35,990

Good Deal
Virginia Beach, VA
47 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:
White
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic Overdrive
Mileage:
39,495
Stock number:
191384MT
VIN:
1GCPYFED3KZ191384

Sponsored

2019 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

85,895 miles

$32,473

Fair Deal
Chesapeake, VA
42 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:
Northsky Blue Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
85,895
Stock number:
QX00235
VIN:
3GCPYFED6KG189788

Sponsored

2024 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

54,130 miles

$44,647

Good Deal
Store transfer to Newport News, VA
1,075 mi away • Price includes $649 shipping Price includes $649 shipping
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:
White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
54,130
Stock number:
27860462
VIN:
3GCUDFED5RG281189

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

39,495 miles

$35,990

Good Deal
Virginia Beach, VA
47 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:
White
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic Overdrive
Mileage:
39,495
Stock number:
191384MT
VIN:
1GCPYFED3KZ191384

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

34,194 miles

$43,300

Good Deal
Hopewell, VA
34 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:
Red Hot
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
34,194
Stock number:
260154A
VIN:
1GCPYFED8NZ220897

Sponsored

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

  • Chevrolet Silverado 1500 RST in Williamsburg VA

  • Chevrolet Silverado 1500 LTZ in Williamsburg VA

  • Chevrolet Silverado 1500 LT Trail Boss in Williamsburg VA

  • Chevrolet Silverado 1500 LT1 in Williamsburg VA

  • Chevrolet Silverado 1500 Custom in Williamsburg VA

  • Chevrolet Silverado 1500 High Country in Williamsburg VA

  • Chevrolet Silverado 1500 Custom Trail Boss in Williamsburg VA

  • Chevrolet Silverado 1500 Work Truck in Williamsburg VA

  • Chevrolet Silverado 1500 in Norfolk VA

  • Chevrolet Silverado 1500 in Richmond VA

  • Chevrolet Silverado 1500 in Elizabeth City NC

  • Chevrolet Silverado 1500 in Fredericksburg VA

  • Chevrolet Silverado 1500 in Salisbury MD

  • Chevrolet Silverado 1500 in Rocky Mount NC

  • Chevrolet Silverado 1500 in Manassas VA

  • Chevrolet Silverado 1500 in Charlottesville VA

  • Chevrolet Silverado 1500 in Washington DC

  • Chevrolet Silverado 1500 in Williamsburg VA

  • Old Chevy Trucks for Sale in Williamsburg VA

  • Classic Muscle Cars for Sale in Williamsburg VA

  • Chevrolet Trucks For Sale in Williamsburg VA

  • Cheap Muscle Cars for Sale in Williamsburg VA

  • Work Trucks for Sale in Williamsburg VA

  • Reliable Cars For Sale in Williamsburg VA

  • American Made Trucks For Sale in Williamsburg VA

  • Best Pickup Trucks For Sale in Williamsburg VA

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

  • 2019 Chevrolet Silverado 1500 LT Trail Boss in Williamsburg 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

  • Strosnider Chevrolet

  • Tappahannock Chevrolet

  • Southern Chevrolet

  • Casey Chevrolet

  • CMA's Colonial Chevrolet

  • Ken Houtz Chevrolet Inc.

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.