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 Ridge, MI

149 results
Pleasant Ridge, MI
2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Michael Bates Chevrolet

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

21,274 miles

$37,949

Good Deal
Woodhaven, MI
24 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:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
21,274
Stock number:
P16834
VIN:
3GCPYCEL8NG203684

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

94,539 miles

$28,500

Good Deal
Waterford, MI
19 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:
Glacier Blue Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
94,539
Stock number:
NG597618A
VIN:
3GCPDCED7NG597618

Sponsored

2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

30,756 miles

$35,800

Good Deal
Certified Pre-Owned
Flint, MI
49 mi away
Year:
2023
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:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
30,756
Stock number:
P35273
VIN:
3GCPDCEK4PG237997

Sponsored

2020 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

64,737 miles

$28,383

Fair Deal
Lake Orion, MI
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:
Shadow Gray Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
64,737
Stock number:
T27050A
VIN:
1GCRYCEF8LZ285612

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,144 miles

$29,618

Great Deal
Monroe, MI
42 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Shadow Gray Metallic
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
55,144
Stock number:
M218438M
VIN:
1GCPYCEK3NZ218438

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

95,361 miles

$23,585

Great Deal
Brighton, MI
35 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:
Summit White
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
95,361
Stock number:
B5548
VIN:
1GCPYCEH4LZ301023

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

28,599 miles

$37,300

Good Deal
Certified Pre-Owned
Flint, MI
49 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:
Dark Ash Metallic
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
28,599
Stock number:
P35080
VIN:
3GCPDCEK1RG168396

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

105,655 miles

$23,877

Fair Deal
New Hudson, MI
24 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:
Northsky Blue Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
105,655
Stock number:
LZ113117
VIN:
1GCRYCEF6LZ133117

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

94,539 miles

$28,500

Good Deal
Waterford, MI
19 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:
Glacier Blue Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
94,539
Stock number:
NG597618A
VIN:
3GCPDCED7NG597618

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

126,562 miles

$20,995

Good Deal
Highland, MI
29 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:
Red Hot
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
126,562
Stock number:
JX6T214657A
VIN:
1GCRYCEFXKZ331598

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

76,327 miles

$27,087

Fair Deal
Waterford, MI
17 mi away
Year:
2019
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:
Black
Combined gas mileage:
17 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
76,327
Stock number:
KZ272249
VIN:
1GCRYCEH5KZ272249

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

60,302 miles

$33,895

Fair Deal
Highland, MI
29 mi away
Year:
2021
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:
60,302
Stock number:
PJA101021
VIN:
1GCPYCEL0MZ101021

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Michigan
  6. / Pleasant Ridge
  • Chevrolet Silverado 1500 LT in Pleasant Ridge MI

  • Chevrolet Silverado 1500 RST in Pleasant Ridge MI

  • Chevrolet Silverado 1500 LTZ in Pleasant Ridge MI

  • Chevrolet Silverado 1500 LT Trail Boss in Pleasant Ridge MI

  • Chevrolet Silverado 1500 LT1 in Pleasant Ridge MI

  • Chevrolet Silverado 1500 High Country in Pleasant Ridge MI

  • Chevrolet Silverado 1500 Custom in Pleasant Ridge MI

  • Chevrolet Silverado 1500 Custom Trail Boss in Pleasant Ridge MI

  • Chevrolet Silverado 1500 Work Truck in Pleasant Ridge MI

  • Chevrolet Silverado 1500 in Detroit MI

  • Chevrolet Silverado 1500 in Lake Orion MI

  • Chevrolet Silverado 1500 in Ann Arbor MI

  • Chevrolet Silverado 1500 in Howell MI

  • Chevrolet Silverado 1500 in Flint MI

  • Chevrolet Silverado 1500 in Toledo OH

  • Chevrolet Silverado 1500 in Jackson MI

  • Chevrolet Silverado 1500 in Lansing MI

  • Chevrolet Silverado 1500 in Saginaw MI

  • Chevrolet Silverado 1500 in Pleasant Ridge MI

  • Old Chevy Trucks for Sale in Pleasant Ridge MI

  • Classic Muscle Cars for Sale in Pleasant Ridge MI

  • Chevrolet Trucks For Sale in Pleasant Ridge MI

  • Cheap Muscle Cars for Sale in Pleasant Ridge MI

  • Work Trucks for Sale in Pleasant Ridge MI

  • Reliable Cars For Sale in Pleasant Ridge MI

  • American Made Trucks For Sale in Pleasant Ridge MI

  • Best Pickup Trucks For Sale in Pleasant Ridge MI

  • Best Cars Under $5,000 For Sale in Pleasant Ridge MI

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Pleasant Ridge MI

  • 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

  • Shea Chevrolet Buick GMC

  • Serra Chevrolet Sterling Heights

  • Serra Chevrolet Southfield

  • Champion Chevrolet of Howell

  • Feldman Chevrolet of Livonia

  • George Matick Chevrolet

  • Feldman Chevrolet of New Hudson

  • LaFontaine Chevrolet

  • Rinke Chevrolet-Buick-GMC

  • Moran Chevrolet

  • LaFontaine Chevrolet of Plymouth

  • Les Stanford 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.