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 Upperville, VA

305 results
Rectortown, VA
2023 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD Lindsay Chevrolet of Front Royal

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

52,686 miles

$43,995

Good Deal
Certified Pre-Owned
Front Royal, VA
18 mi away
Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Black
Combined gas mileage:
24 MPG
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
52,686
Stock number:
R26074A
VIN:
3GCUDFE83PG115897

Sponsored

2020 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

59,991 miles

$35,000

Good Deal
Winchester, VA
23 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:
Cajun Red Tintcoat
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
59,991
Stock number:
T1363A
VIN:
1GCPYFED7LZ317909

Sponsored

2020 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

45,763 miles

$36,700

Fair Deal
Stafford, VA
39 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:
Jet Black
Transmission:
Automatic
Mileage:
45,763
Stock number:
GAM5890
VIN:
1GCPYFEDXLZ335112

Sponsored

2022 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

40,654 miles

$37,500

Great Deal
Woodbridge, VA
38 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Northsky Blue Metallic
Interior color:
Black
Transmission:
Automatic
Mileage:
40,654
Stock number:
H28949A
VIN:
3GCPYFELXNG121280

2020 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

63,370 miles

$32,500

Good Deal
Woodbridge, VA
38 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:
63,370
Stock number:
H29169A
VIN:
1GCPYFED8LZ222050

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

59,991 miles

$35,000

Good Deal
Winchester, VA
23 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:
Cajun Red Tintcoat
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
59,991
Stock number:
T1363A
VIN:
1GCPYFED7LZ317909

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

27,690 miles

$51,250

Good Deal
Woodbridge, VA
38 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:
Black
Fuel type:
Diesel
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
27,690
Stock number:
H29232A
VIN:
3GCUKFE8XSG100988

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

105,815 miles

$29,977

Fair Deal
Stafford, VA
39 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
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic Overdrive
Mileage:
105,815
Stock number:
214479
VIN:
1GCPYFEDXKZ214479

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

35,817 miles

$45,900

Good Deal
Certified Pre-Owned
Wheaton, MD
44 mi away
Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Dark Ash Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
35,817
Stock number:
FPA10738
VIN:
3GCUDFEL6PG323972

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

40,654 miles

$37,500

Great Deal
Woodbridge, VA
38 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Northsky Blue Metallic
Interior color:
Black
Transmission:
Automatic
Mileage:
40,654
Stock number:
H28949A
VIN:
3GCPYFELXNG121280

Sponsored

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

  • Chevrolet Silverado 1500 LT in Upperville VA

  • Chevrolet Silverado 1500 RST in Upperville VA

  • Chevrolet Silverado 1500 LTZ in Upperville VA

  • Chevrolet Silverado 1500 LT Trail Boss in Upperville VA

  • Chevrolet Silverado 1500 LT1 in Upperville VA

  • Chevrolet Silverado 1500 High Country in Upperville VA

  • Chevrolet Silverado 1500 Custom in Upperville VA

  • Chevrolet Silverado 1500 Custom Trail Boss in Upperville VA

  • Chevrolet Silverado 1500 Work Truck in Upperville VA

  • Chevrolet Silverado 1500 in Winchester VA

  • Chevrolet Silverado 1500 in Manassas VA

  • Chevrolet Silverado 1500 in Washington DC

  • Chevrolet Silverado 1500 in Hagerstown MD

  • Chevrolet Silverado 1500 in Fredericksburg VA

  • Chevrolet Silverado 1500 in Harrisonburg VA

  • Chevrolet Silverado 1500 in Cumberland MD

  • Chevrolet Silverado 1500 in Baltimore MD

  • Chevrolet Silverado 1500 in Charlottesville VA

  • Chevrolet Silverado 1500 in Upperville VA

  • Old Chevy Trucks for Sale in Upperville VA

  • Classic Muscle Cars for Sale in Upperville VA

  • Chevrolet Trucks For Sale in Upperville VA

  • Cheap Muscle Cars for Sale in Upperville VA

  • Work Trucks for Sale in Upperville VA

  • Reliable Cars For Sale in Upperville VA

  • American Made Trucks For Sale in Upperville VA

  • Best Pickup Trucks For Sale in Upperville VA

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

  • 2019 Chevrolet Silverado 1500 LT Trail Boss in Upperville 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

  • Koons Tysons Chevrolet GMC

  • Country Chevrolet, Inc.

  • Ourisman Chevrolet of Rockville

  • Criswell Chevrolet, Inc.

  • Fitzgerald Frederick

  • Lindsay Chevrolet of Front Royal

  • Ourisman Chevrolet Buick GMC of Alexandria

  • Michelle Radley Chevrolet

  • CMA's Chevrolet of Martinsburg and CMA's Toyota of Martinsburg

  • Fort Washington Chevrolet

  • Fitzgerald Hagerstown

  • Battlefield 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

© 2025 CarGurus, Inc., All Rights Reserved.