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 Upperville, VA

148 results
Rectortown, VA
2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Malloy Chevrolet-Cadillac

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

5,577 miles

$50,000

Fair Deal
Winchester, VA
23 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:
Sterling Gray Metallic
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
5,577
Stock number:
R284174
VIN:
3GCUKCED4SG284174

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

17,427 miles

$43,900

Good Deal
Woodbridge, VA
38 mi away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Summit White
Combined gas mileage:
25 MPG
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
17,427
Stock number:
HP9460
VIN:
3GCUDCE81RG264438

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

108,561 miles

$24,995

Fair Deal
Sterling, VA
20 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:
Gray
Transmission:
6-Speed Automatic Overdrive
Mileage:
108,561
Stock number:
LB293628
VIN:
1GCRYCEFXKZ293628

Sponsored

2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

72,842 miles

$33,295

Good Deal
Alexandria, VA
44 mi away
Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Gray
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
72,842
Stock number:
0N16018A
VIN:
3GCPDCEK4PG189224

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

62,807 miles

$34,179

Good Deal
Certified Pre-Owned
Front Royal, VA
18 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:
Shadow Gray Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
62,807
Stock number:
R26053A
VIN:
1GCPYCEF2MZ220067

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

29,165 miles

$39,243

Fair Deal
Springfield, VA
38 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:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
29,165
Stock number:
GCKE174H
VIN:
3GCPDCEK3RG276938

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

62,807 miles

$34,179

Good Deal
Certified Pre-Owned
Front Royal, VA
18 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:
Shadow Gray Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
62,807
Stock number:
R26053A
VIN:
1GCPYCEF2MZ220067

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom 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 Custom 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.