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 Middletown, DE

144 results
Middletown, DE
2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

17,031 miles

$42,386

Fair Deal
Certified Pre-Owned
Cherry Hill, NJ
47 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:
Glacier Blue Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black, Cloth Seat Trim
Transmission:
Automatic
Mileage:
17,031
Stock number:
62532
VIN:
3GCUDCED9PG362532

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,945 miles

$32,997

Great Deal
Dover, DE
25 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:
Cherry Red Tintcoat
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black, Cloth seat trim
Transmission:
Automatic
Mileage:
59,945
Stock number:
26142A
VIN:
1GCPYCEF8MZ420032

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

40,100 miles

$34,500

Good Deal
White Marsh, MD
42 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
40,100
Stock number:
KWMP220468
VIN:
3GCPDCEKXNG508834

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,945 miles

$32,997

Great Deal
Dover, DE
25 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:
Cherry Red Tintcoat
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black, Cloth seat trim
Transmission:
Automatic
Mileage:
59,945
Stock number:
26142A
VIN:
1GCPYCEF8MZ420032

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

36,872 miles

$35,899

Good Deal
Certified Pre-Owned
Marlton, NJ
49 mi away
Year:
2022
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
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
36,872
Stock number:
60639
VIN:
3GCPDCEK3NG583391

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

41,640 miles

$31,000

Great Deal
White Marsh, MD
42 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
310 hp 2.7L I4
Exterior color:
Red
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
41,640
Stock number:
KCCP220134A
VIN:
3GCPYCEK5NG145251

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

49,188 miles

$37,000

Good Deal
Dover, DE
25 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Dark Ash Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black, Cloth seat trim
Transmission:
Automatic
Mileage:
49,188
Stock number:
26172A
VIN:
3GCPDCED4NG679127

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Delaware
  6. / Middletown
  • Chevrolet Silverado 1500 LT in Middletown DE

  • Chevrolet Silverado 1500 RST in Middletown DE

  • Chevrolet Silverado 1500 LTZ in Middletown DE

  • Chevrolet Silverado 1500 LT Trail Boss in Middletown DE

  • Chevrolet Silverado 1500 LT1 in Middletown DE

  • Chevrolet Silverado 1500 Custom in Middletown DE

  • Chevrolet Silverado 1500 High Country in Middletown DE

  • Chevrolet Silverado 1500 Custom Trail Boss in Middletown DE

  • Chevrolet Silverado 1500 Work Truck in Middletown DE

  • Chevrolet Silverado 1500 in Newark DE

  • Chevrolet Silverado 1500 in Dover DE

  • Chevrolet Silverado 1500 in Philadelphia PA

  • Chevrolet Silverado 1500 in Baltimore MD

  • Chevrolet Silverado 1500 in Lancaster PA

  • Chevrolet Silverado 1500 in Reading PA

  • Chevrolet Silverado 1500 in Atlantic City NJ

  • Chevrolet Silverado 1500 in Hanover PA

  • Chevrolet Silverado 1500 in Trenton NJ

  • Chevrolet Silverado 1500 in Middletown DE

  • Old Chevy Trucks for Sale in Middletown DE

  • Classic Muscle Cars for Sale in Middletown DE

  • Chevrolet Trucks For Sale in Middletown DE

  • Cheap Muscle Cars for Sale in Middletown DE

  • Work Trucks for Sale in Middletown DE

  • Reliable Cars For Sale in Middletown DE

  • American Made Trucks For Sale in Middletown DE

  • Best Pickup Trucks For Sale in Middletown DE

  • Best Cars Under $5,000 For Sale in Middletown DE

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Middletown DE

  • 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 White Marsh Chevrolet

  • Nucar Chevrolet of New Castle

  • Chapman Chevrolet

  • AutoNation Chevrolet Timonium

  • Adams Chevrolet

  • Videon Chevrolet of Phoenixville

  • Willis Chevrolet

  • Hertrich Chevrolet of Dover

  • John Sauder Chevrolet of New Holland

  • Miracle Chevrolet of Morgantown

  • i.g. Burton Chevrolet of Milford

  • Ciocca Chevrolet Of West Chester

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.