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 Philadelphia, TN

194 results
Loudon, TN
2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD John Megel Chevrolet, Llc

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

83,987 miles

$32,122

Fair Deal
Dawsonville, GA
98 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 Hot
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
83,987
Stock number:
T254071A
VIN:
3GCPDCEK0NG686803

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

25,000 miles

$37,995

Good Deal
Cumming, GA
100 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:
Gray
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
25,000
Stock number:
J109637A
VIN:
3GCPDCEK7RG214944

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

13,602 miles

$45,547

Fair Deal
Chattanooga, TN
66 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:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
13,602
Stock number:
C26291A
VIN:
3GCUDCED7RG418356

Sponsored

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

31,288 miles

$36,917

Fair Deal
La Follette, TN
44 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:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
31,288
Stock number:
P8910
VIN:
1GCPYCEF0MZ419523

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

4,502 miles

$40,699

Great Deal
Certified Pre-Owned
Morristown, TN
68 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:
4,502
Stock number:
18765A
VIN:
3GCPDCEK1RG354732

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

53,849 miles

$34,629

Fair Deal
La Follette, TN
44 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:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
53,849
Stock number:
P9035
VIN:
1GCPYCEF2MZ413142

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Tennessee
  6. / Philadelphia
  • Chevrolet Silverado 1500 LT in Philadelphia TN

  • Chevrolet Silverado 1500 RST in Philadelphia TN

  • Chevrolet Silverado 1500 LTZ in Philadelphia TN

  • Chevrolet Silverado 1500 LT Trail Boss in Philadelphia TN

  • Chevrolet Silverado 1500 LT1 in Philadelphia TN

  • Chevrolet Silverado 1500 High Country in Philadelphia TN

  • Chevrolet Silverado 1500 Custom in Philadelphia TN

  • Chevrolet Silverado 1500 Custom Trail Boss in Philadelphia TN

  • Chevrolet Silverado 1500 Work Truck in Philadelphia TN

  • Chevrolet Silverado 1500 in Knoxville TN

  • Chevrolet Silverado 1500 in Crossville TN

  • Chevrolet Silverado 1500 in Chattanooga TN

  • Chevrolet Silverado 1500 in Cookeville TN

  • Chevrolet Silverado 1500 in Dalton GA

  • Chevrolet Silverado 1500 in Morristown TN

  • Chevrolet Silverado 1500 in Greeneville TN

  • Chevrolet Silverado 1500 in Canton GA

  • Chevrolet Silverado 1500 in Gainesville GA

  • Chevrolet Silverado 1500 in Philadelphia TN

  • Old Chevy Trucks for Sale in Philadelphia TN

  • Classic Muscle Cars for Sale in Philadelphia TN

  • Chevrolet Trucks For Sale in Philadelphia TN

  • Cheap Muscle Cars for Sale in Philadelphia TN

  • Work Trucks for Sale in Philadelphia TN

  • Reliable Cars For Sale in Philadelphia TN

  • American Made Trucks For Sale in Philadelphia TN

  • Best Pickup Trucks For Sale in Philadelphia TN

  • Best Cars Under $5,000 For Sale in Philadelphia TN

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Philadelphia TN

  • 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

  • Tim Short Ford of LaFollette

  • Reeder Chevrolet

  • Long Chevrolet Buick GMC

  • Dave Kirk Chevrolet GMC

  • Don Ledford Automotive

  • Volunteer 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.