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 Freeport, MI

190 results
Freeport, MI
2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Feldman Chevrolet of New Hudson

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

52,260 miles

$33,433

Fair Deal
New Hudson, MI
87 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:
Shadow Gray Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
52,260
Stock number:
LX6T169890A
VIN:
1GCPYCEF9MZ289368

Sponsored

2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

82,670 miles

$33,500

Good Deal
Birch Run, MI
83 mi away
Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Summit White
Combined gas mileage:
24 MPG
Fuel type:
Diesel
Interior color:
Jet Black, Cloth Seat Trim
Transmission:
Automatic
Mileage:
82,670
Stock number:
360386A
VIN:
3GCUDCE85PG275827

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
95 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

2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

142,272 miles

$18,995

Great Deal
Mt Pleasant, MI
65 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
Fuel type:
Gasoline
Mileage:
142,272
Stock number:
60-27874A
VIN:
1GCRYCEF3KZ362109

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

90,496 miles

$29,595

Good Deal
Allegan, MI
32 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:
90,496
Stock number:
BB5476A
VIN:
1GCPYCEF3MZ231546

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

45,774 miles

$35,398

Good Deal
Adrian, MI
88 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:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
45,774
Stock number:
W25401A
VIN:
1GCPYCEL3NZ112855

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
79 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

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

100,278 miles

$26,237

Good Deal
Freeland, MI
79 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:
Black
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
100,278
Stock number:
P8767A
VIN:
3GCPYCEF7KG272016

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

30,756 miles

$35,600

Great Deal
Certified Pre-Owned
Flint, MI
79 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

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

33,181 miles

$34,500

Good Deal
Certified Pre-Owned
Eaton Rapids, MI
37 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Red Hot
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
33,181
Stock number:
TT25277A
VIN:
1GCPYCEK4NZ112399

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

101,671 miles

$25,000

Good Deal
Certified Pre-Owned
Eaton Rapids, MI
37 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:
101,671
Stock number:
UT619
VIN:
3GCPYCEFXKG172797

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

73,612 miles

$30,498

Good Deal
Grand Haven, MI
51 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:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
73,612
Stock number:
B16417
VIN:
1GCPYCEF1MZ199891

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

58,373 miles

$32,984

Good Deal
Muskegon, MI
53 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:
58,373
Stock number:
T260129A
VIN:
1GCPYCEL6MZ267706

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

100,815 miles

$25,282

Good Deal
Saginaw, MI
83 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:
Gray (Satin Steel Metallic)
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
100,815
Stock number:
LZ122887A
VIN:
1GCPYCEF1LZ122887

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

90,175 miles

$29,895

Fair Deal
Hillsdale, MI
65 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:
Oxford Brown Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black Cloth Seat Trim
Transmission:
Automatic
Mileage:
90,175
Stock number:
25477B
VIN:
1GCPYCEF3MZ376389

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

69,588 miles

$28,997

Fair Deal
Grand Haven, MI
51 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:
Summit White
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
69,588
Stock number:
B16554
VIN:
1GCRYCEF3KZ238793

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

23,472 miles

$37,750

Good Deal
Charlotte, MI
28 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:
23,472
Stock number:
CT9947A
VIN:
3GCPDCEK1RG116234

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

54,285 miles

$32,078

Great Deal
Grand Rapids, MI
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:
Gray (Satin Steel Metallic)
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
54,285
Stock number:
J25240A
VIN:
1GCPYCEF4MZ305542

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

65,744 miles

$30,489

Good Deal
Corunna, MI
63 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:
Black
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
65,744
Stock number:
C0474B
VIN:
1GCPYCEF7LZ146174

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

82,670 miles

$33,500

Good Deal
Birch Run, MI
83 mi away
Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Summit White
Combined gas mileage:
24 MPG
Fuel type:
Diesel
Interior color:
Jet Black, Cloth Seat Trim
Transmission:
Automatic
Mileage:
82,670
Stock number:
360386A
VIN:
3GCUDCE85PG275827

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

100,278 miles

$26,237

Good Deal
Freeland, MI
79 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:
Black
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
100,278
Stock number:
P8767A
VIN:
3GCPYCEF7KG272016

Sponsored

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

  • Chevrolet Silverado 1500 RST in Freeport MI

  • Chevrolet Silverado 1500 LTZ in Freeport MI

  • Chevrolet Silverado 1500 LT Trail Boss in Freeport MI

  • Chevrolet Silverado 1500 LT1 in Freeport MI

  • Chevrolet Silverado 1500 High Country in Freeport MI

  • Chevrolet Silverado 1500 Custom in Freeport MI

  • Chevrolet Silverado 1500 Custom Trail Boss in Freeport MI

  • Chevrolet Silverado 1500 Work Truck in Freeport MI

  • Chevrolet Silverado 1500 in Grand Rapids MI

  • Chevrolet Silverado 1500 in Kalamazoo MI

  • Chevrolet Silverado 1500 in Lansing MI

  • Chevrolet Silverado 1500 in Holland MI

  • Chevrolet Silverado 1500 in Muskegon MI

  • Chevrolet Silverado 1500 in Jackson MI

  • Chevrolet Silverado 1500 in Mount Pleasant MI

  • Chevrolet Silverado 1500 in Howell MI

  • Chevrolet Silverado 1500 in Saginaw MI

  • Chevrolet Silverado 1500 in Freeport MI

  • Old Chevy Trucks for Sale in Freeport MI

  • Classic Muscle Cars for Sale in Freeport MI

  • Chevrolet Trucks For Sale in Freeport MI

  • Cheap Muscle Cars for Sale in Freeport MI

  • Work Trucks for Sale in Freeport MI

  • Reliable Cars For Sale in Freeport MI

  • American Made Trucks For Sale in Freeport MI

  • Best Pickup Trucks For Sale in Freeport MI

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

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Freeport 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

  • Robert DeNooyer Chevrolet

  • Todd Wenzel Chevrolet

  • Bookwalter Chevrolet Buick

  • Baker Chevrolet Allegan

  • Fox Chevrolet

  • Preferred Chevrolet Buick GMC

  • Shaheen Chevrolet

  • Midway 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.