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 Princess Anne, MD

299 results
Princess Anne, MD
2020 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD Hyundai of Dundalk

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

54,411 miles

$34,000

Good Deal
Dundalk, MD
87 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:
Gray (Satin Steel Metallic)
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
54,411
Stock number:
H106552
VIN:
3GCPYFED0LG106552

Sponsored

2020 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

127,617 miles

$25,595

Good Deal
Falls Church, VA
93 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
Fuel type:
Gasoline
Mileage:
127,617
Stock number:
M340969
VIN:
3GCPYFED8LG340969

Sponsored

2021 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

70,354 miles

$34,988

Fair 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:
355 hp 5.3L V8
Exterior color:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
70,354
Stock number:
143836W
VIN:
3GCPYFED0MG356326

Sponsored

2021 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

79,850 miles

$34,980

Fair Deal
Baltimore, MD
96 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:
Gray
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
79,850
Stock number:
5131
VIN:
1GCPYFED2MZ105131

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
90 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

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

63,370 miles

$31,994

Good Deal
Woodbridge, VA
90 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

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

37,986 miles

$39,865

Good Deal
Pocomoke City, MD
14 mi away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Black
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
37,986
Stock number:
P0300
VIN:
1GCPYFEL2MZ385754

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
98 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

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

127,617 miles

$25,595

Good Deal
Falls Church, VA
93 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
Fuel type:
Gasoline
Mileage:
127,617
Stock number:
M340969
VIN:
3GCPYFED8LG340969

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

96,495 miles

$32,997

Fair Deal
Yorktown, VA
83 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:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
96,495
Stock number:
397
VIN:
1GCPYFED0LZ329027

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

43,444 miles

$38,977

Fair Deal
Salisbury, MD
16 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:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
43,444
Stock number:
126148A
VIN:
1GCPYFED6MZ171844

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

66,905 miles

$36,997

Fair Deal
Glen Burnie, MD
83 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:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
66,905
Stock number:
60565A
VIN:
1GCPYFED1MZ421443

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

28,336 miles

$47,776

Good Deal
Bel Air, MD
98 mi away
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:
Gray
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
28,336
Stock number:
G5458A
VIN:
3GCUDFED1RG387932

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

76,697 miles

$34,000

Good Deal
Baltimore, MD
96 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:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
76,697
Stock number:
KBF260682B
VIN:
3GCPYFED4MG400909

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

130,004 miles

$29,997

Fair Deal
Vineland, NJ
93 mi away
Year:
2020
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:
130,004
Stock number:
p11325
VIN:
3GCPYFEL5LG395533

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / LT 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 Custom in Princess Anne MD

  • Chevrolet Silverado 1500 High Country 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 LT 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

  • First State Chevrolet

  • i.g. Burton Chevrolet of Seaford

  • i.g. Burton Chevrolet/CDJRF of Berlin

  • Hertrich Chevrolet Cadillac of Salisbury

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.