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 Princess Anne, MD

158 results
Princess Anne, MD
2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD Ourisman Chevrolet of Bowie

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

70,126 miles

$25,859

Good Deal
Bowie, MD
76 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

2026 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

449 miles

$47,000

Good Deal
Certified Pre-Owned
Fredericksburg, VA
97 mi away
Year:
2026
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
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black, Cloth seat trim
Transmission:
Automatic
Mileage:
449
Stock number:
DX7261A
VIN:
3GCPKCEK6TG138839

Sponsored

2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

24,739 miles

$42,095

Fair Deal
Georgetown, DE
37 mi away
Year:
2023
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:
24,739
Stock number:
190401
VIN:
3GCUDCED6PG136206

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
76 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

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

36,304 miles

$37,900

Fair Deal
Woodbridge, VA
90 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

14,485 miles

$35,999

Great Deal
Baltimore, MD
88 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

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,336 miles

$33,200

Fair Deal
Silver Spring, MD
91 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

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

15,574 miles

$42,995

Fair Deal
Certified Pre-Owned
Georgetown, DE
37 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:
Black
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
15,574
Stock number:
434100
VIN:
3GCPDCEK8RG266633

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
93 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

83,746 miles

$29,981

Great Deal
Fredericksburg, VA
97 mi away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
83,746
Stock number:
O188447A
VIN:
3GCPYCEL6MG481465

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
93 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. / Princess Anne
  • Chevrolet Silverado 1500 LT in Princess Anne MD

  • Chevrolet Silverado 1500 RST in Princess Anne MD

  • Chevrolet Silverado 1500 LTZ in Princess Anne MD

  • Chevrolet Silverado 1500 LT Trail Boss in Princess Anne MD

  • Chevrolet Silverado 1500 LT1 in Princess Anne MD

  • Chevrolet Silverado 1500 High Country in Princess Anne MD

  • Chevrolet Silverado 1500 Custom in Princess Anne MD

  • Chevrolet Silverado 1500 Custom Trail Boss in Princess Anne MD

  • Chevrolet Silverado 1500 Work Truck in Princess Anne MD

  • Chevrolet Silverado 1500 in Salisbury MD

  • Chevrolet Silverado 1500 in Dover DE

  • Chevrolet Silverado 1500 in Williamsburg VA

  • Chevrolet Silverado 1500 in Washington DC

  • Chevrolet Silverado 1500 in Baltimore MD

  • Chevrolet Silverado 1500 in Fredericksburg VA

  • Chevrolet Silverado 1500 in Norfolk VA

  • Chevrolet Silverado 1500 in Newark DE

  • Chevrolet Silverado 1500 in Manassas VA

  • Chevrolet Silverado 1500 in Princess Anne MD

  • Old Chevy Trucks for Sale in Princess Anne MD

  • Classic Muscle Cars for Sale in Princess Anne MD

  • Chevrolet Trucks For Sale in Princess Anne MD

  • Cheap Muscle Cars for Sale in Princess Anne MD

  • Work Trucks for Sale in Princess Anne MD

  • Reliable Cars For Sale in Princess Anne MD

  • American Made Trucks For Sale in Princess Anne MD

  • Best Pickup Trucks For Sale in Princess Anne MD

  • Best Cars Under $5,000 For Sale in Princess Anne MD

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Princess Anne 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

  • Lexington Park Chevrolet Buick GMC

  • i.g. Burton Lewes Automall

  • i.g. Burton Chevrolet of Seaford

  • First State Chevrolet

  • Hertrich Chevrolet Cadillac of Salisbury

  • Hertrich 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.