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 Silver Spring, MD

167 results
Silver Spring, MD
2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Jim McKay Chevrolet Inc

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

4,444 miles

$43,000

Fair Deal
Fairfax, VA
20 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:
Sterling Gray Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
10-Speed Automatic
Mileage:
4,444
Stock number:
SP3287
VIN:
3GCPKCEK9SG354487

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

70,126 miles

$25,859

Good Deal
Bowie, MD
17 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:
Red Hot
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
70,126
Stock number:
215368A
VIN:
1GCRYCEF1KZ211107

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

20,685 miles

$39,931

Fair Deal
Thurmont, MD
46 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:
Black
Transmission:
8-Speed Automatic
Mileage:
20,685
Stock number:
Q260257A
VIN:
3GCPDCEK6RG429893

Sponsored

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

70,126 miles

$25,859

Good Deal
Bowie, MD
17 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:
Red Hot
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
70,126
Stock number:
215368A
VIN:
1GCRYCEF1KZ211107

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

14,485 miles

$35,999

Great Deal
Baltimore, MD
32 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:
Red Hot
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
14,485
Stock number:
C260194A
VIN:
1GCPYCEF4MZ265821

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

36,304 miles

$37,900

Fair Deal
Woodbridge, VA
32 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:
Sterling Gray Metallic
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
36,304
Stock number:
HP9569
VIN:
3GCPDCEK3PG311751

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

133,470 miles

$22,995

Good Deal
Stafford, VA
41 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:
Blue
Fuel type:
Gasoline
Interior color:
Gray
Mileage:
133,470
Stock number:
DMV1729
VIN:
3GCPYCEF1MG260401

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,336 miles

$33,200

Good Deal
Silver Spring, MD
5 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:
Jet Black
Transmission:
Automatic
Mileage:
55,336
Stock number:
A10858
VIN:
1GCPYCEFXMZ264883

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

133,470 miles

$22,995

Good Deal
Stafford, VA
41 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:
Blue
Fuel type:
Gasoline
Interior color:
Gray
Mileage:
133,470
Stock number:
DMV1729
VIN:
3GCPYCEF1MG260401

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Maryland
  6. / Silver Spring
  • Chevrolet Silverado 1500 LT in Silver Spring MD

  • Chevrolet Silverado 1500 RST in Silver Spring MD

  • Chevrolet Silverado 1500 LTZ in Silver Spring MD

  • Chevrolet Silverado 1500 LT Trail Boss in Silver Spring MD

  • Chevrolet Silverado 1500 LT1 in Silver Spring MD

  • Chevrolet Silverado 1500 High Country in Silver Spring MD

  • Chevrolet Silverado 1500 Custom in Silver Spring MD

  • Chevrolet Silverado 1500 Custom Trail Boss in Silver Spring MD

  • Chevrolet Silverado 1500 Work Truck in Silver Spring MD

  • Chevrolet Silverado 1500 in Washington DC

  • Chevrolet Silverado 1500 in Baltimore MD

  • Chevrolet Silverado 1500 in Manassas VA

  • Chevrolet Silverado 1500 in Hanover PA

  • Chevrolet Silverado 1500 in Fredericksburg VA

  • Chevrolet Silverado 1500 in Hagerstown MD

  • Chevrolet Silverado 1500 in Winchester VA

  • Chevrolet Silverado 1500 in Lancaster PA

  • Chevrolet Silverado 1500 in Dover DE

  • Chevrolet Silverado 1500 in Silver Spring MD

  • Old Chevy Trucks for Sale in Silver Spring MD

  • Classic Muscle Cars for Sale in Silver Spring MD

  • Chevrolet Trucks For Sale in Silver Spring MD

  • Cheap Muscle Cars for Sale in Silver Spring MD

  • Work Trucks for Sale in Silver Spring MD

  • Reliable Cars For Sale in Silver Spring MD

  • American Made Trucks For Sale in Silver Spring MD

  • Best Pickup Trucks For Sale in Silver Spring MD

  • Best Cars Under $5,000 For Sale in Silver Spring MD

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Silver Spring MD

  • 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

  • Lindsay Chevrolet of Woodbridge

  • Ourisman Chevrolet of Marlow Heights

  • Country Chevrolet, Inc.

  • Koons Clarksville Chevrolet GMC

  • Koons Tysons Chevrolet GMC

  • Koons White Marsh Chevrolet

  • JBA Chevrolet

  • Ourisman Chevrolet of Rockville

  • Anderson Buick GMC

  • Criswell Chevrolet, Inc.

  • Fitzgerald Frederick

  • Len Stoler 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

© 2026 CarGurus, Inc., All Rights Reserved.