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 Madison, AL

204 results
Madison, AL
2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Bill Smith Buick GMC

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

8,219 miles

$45,987

Fair Deal
Cullman, AL
35 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:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
8,219
Stock number:
59587A
VIN:
3GCUDCED3RG366188

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

20,722 miles

$45,120

Fair Deal
Guntersville, AL
38 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:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
20,722
Stock number:
C2595A
VIN:
3GCUDCED8RG446649

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

125,153 miles

$27,291

Fair Deal
Huntsville, AL
5 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:
Northsky Blue Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
125,153
Stock number:
6C2173A
VIN:
3GCPDCEK1NG573524

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

47,083 miles

$36,990

Fair Deal
Certified Pre-Owned
Decatur, AL
17 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 (Satin Steel Metallic)
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
47,083
Stock number:
108315AG
VIN:
3GCPYCEF5MG108315

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

42,056 miles

$34,658

Good Deal
Tullahoma, TN
55 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
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
42,056
Stock number:
PU8096A
VIN:
1GCPYCEF5MZ258313

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

15,832 miles

$41,995

Great Deal
Fort Payne, AL
61 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:
Gray
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
15,832
Stock number:
67049
VIN:
3GCUKCED2SG199057

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

30,839 miles

$38,396

Good Deal
Certified Pre-Owned
Athens, AL
14 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:
30,839
Stock number:
B25195B
VIN:
3GCPDCEK7RG176924

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

71,162 miles

$28,906

Good Deal
Murfreesboro, TN
82 mi away
Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
4.3L V6 Flex Fuel Vehicle
Exterior color:
Northsky Blue Metallic
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
71,162
Stock number:
X356391A
VIN:
1GCPYCEH1LZ264786

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

85,759 miles

$31,990

Fair Deal
Rome, GA
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:
Black
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic
Mileage:
85,759
VIN:
1GCPYCEF2MZ295660

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

20,590 miles

$42,399

Good Deal
Certified Pre-Owned
Arab, AL
30 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:
Sterling Gray Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
20,590
Stock number:
26-127A
VIN:
3GCUDCED3RG215772

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

31,207 miles

$38,691

Good Deal
Heflin, AL
100 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:
Sterling Gray Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
31,207
Stock number:
134049P
VIN:
3GCUDCED0PG187734

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

61,323 miles

$37,488

Fair Deal
Scottsboro, AL
42 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:
Red Hot
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
61,323
Stock number:
1T624C
VIN:
3GCUDCEDXPG191905

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Alabama
  6. / Madison
  • Chevrolet Silverado 1500 LT in Madison AL

  • Chevrolet Silverado 1500 RST in Madison AL

  • Chevrolet Silverado 1500 LTZ in Madison AL

  • Chevrolet Silverado 1500 LT Trail Boss in Madison AL

  • Chevrolet Silverado 1500 LT1 in Madison AL

  • Chevrolet Silverado 1500 High Country in Madison AL

  • Chevrolet Silverado 1500 Custom in Madison AL

  • Chevrolet Silverado 1500 Custom Trail Boss in Madison AL

  • Chevrolet Silverado 1500 Work Truck in Madison AL

  • Chevrolet Silverado 1500 in Huntsville AL

  • Chevrolet Silverado 1500 in Decatur AL

  • Chevrolet Silverado 1500 in Cullman AL

  • Chevrolet Silverado 1500 in Florence AL

  • Chevrolet Silverado 1500 in Gadsden AL

  • Chevrolet Silverado 1500 in Jasper AL

  • Chevrolet Silverado 1500 in Murfreesboro TN

  • Chevrolet Silverado 1500 in Birmingham AL

  • Chevrolet Silverado 1500 in Chattanooga TN

  • Chevrolet Silverado 1500 in Madison AL

  • Old Chevy Trucks for Sale in Madison AL

  • Classic Muscle Cars for Sale in Madison AL

  • Chevrolet Trucks For Sale in Madison AL

  • Cheap Muscle Cars for Sale in Madison AL

  • Work Trucks for Sale in Madison AL

  • Reliable Cars For Sale in Madison AL

  • American Made Trucks For Sale in Madison AL

  • Best Pickup Trucks For Sale in Madison AL

  • Best Cars Under $5,000 For Sale in Madison AL

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Madison AL

  • 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

  • Landers McLarty Chevrolet

  • Harbin Chevrolet

  • Guntersville Chevrolet

  • Clayton Chevrolet Incorporated

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.