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 Pleasant View, TN

165 results
Pleasant View, TN
2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Gary Mathews Motors Incorporated

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

80,745 miles

$33,250

Fair Deal
Clarksville, TN
19 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:
80,745
Stock number:
L13183
VIN:
1GCPYCEF7MZ266235

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

36,781 miles

$39,230

Great Deal
Mount Juliet, TN
33 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:
Jet Black
Transmission:
Automatic
Mileage:
36,781
Stock number:
RTD2406
VIN:
3GCUDCED8RG214228

Sponsored

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

102,936 miles

$27,995

Fair Deal
Smyrna, TN
44 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:
White
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
102,936
Stock number:
7181
VIN:
1GCPYCEF7LZ123882

Sponsored

2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

2,635 miles

$42,233

Great Deal
Franklin, TN
36 mi away
Year:
2025
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:
Black
Transmission:
8-Speed Automatic
Mileage:
2,635
Stock number:
SF372429A
VIN:
3GCPKCEK5SG294157

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

56,442 miles

$32,725

Good Deal
Nashville, TN
21 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:
Red
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
56,442
Stock number:
3321
VIN:
1GCPYCEF5LZ100195

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

30,234 miles

$40,000

Good Deal
Murfreesboro, TN
49 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:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
30,234
Stock number:
Z225839A
VIN:
3GCUDCED7PG357779

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

145,606 miles

$25,995

Fair Deal
Madison, TN
21 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:
Non-Color
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
145,606
Stock number:
275904
VIN:
1GCPYCEF3MZ275904

Sponsored

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

  • Chevrolet Silverado 1500 RST in Pleasant View TN

  • Chevrolet Silverado 1500 LTZ in Pleasant View TN

  • Chevrolet Silverado 1500 LT Trail Boss in Pleasant View TN

  • Chevrolet Silverado 1500 LT1 in Pleasant View TN

  • Chevrolet Silverado 1500 High Country in Pleasant View TN

  • Chevrolet Silverado 1500 Custom in Pleasant View TN

  • Chevrolet Silverado 1500 Custom Trail Boss in Pleasant View TN

  • Chevrolet Silverado 1500 Work Truck in Pleasant View TN

  • Chevrolet Silverado 1500 in Clarksville TN

  • Chevrolet Silverado 1500 in Nashville TN

  • Chevrolet Silverado 1500 in Lebanon TN

  • Chevrolet Silverado 1500 in Murfreesboro TN

  • Chevrolet Silverado 1500 in Bowling Green KY

  • Chevrolet Silverado 1500 in Cookeville TN

  • Chevrolet Silverado 1500 in Owensboro KY

  • Chevrolet Silverado 1500 in Paducah KY

  • Chevrolet Silverado 1500 in Jackson TN

  • Chevrolet Silverado 1500 in Pleasant View TN

  • Old Chevy Trucks for Sale in Pleasant View TN

  • Classic Muscle Cars for Sale in Pleasant View TN

  • Chevrolet Trucks For Sale in Pleasant View TN

  • Cheap Muscle Cars for Sale in Pleasant View TN

  • Work Trucks for Sale in Pleasant View TN

  • Reliable Cars For Sale in Pleasant View TN

  • American Made Trucks For Sale in Pleasant View TN

  • Best Pickup Trucks For Sale in Pleasant View TN

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

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Pleasant View 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

  • Wilson County Chevrolet Buick GMC

  • Nick Mayer Chevrolet Buick GMC of Dickson

  • Patriot Chevrolet GMC

  • Carl Black Chevrolet

  • Chevrolet Buick Cadillac GMC of Murfreesboro

  • Serra Chevrolet Clarksville

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.