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 Saint Augustine, FL

119 results
Saint Augustine, FL
2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Autoland

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

104,811 miles

$24,435

Great Deal
Jacksonville, FL
33 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:
104,811
Stock number:
4931
VIN:
1GCPYCEFXKZ244064

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

11,617 miles

$43,495

Fair Deal
Jacksonville, FL
37 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:
11,617
Stock number:
26C207A
VIN:
3GCPDCEKXRG198318

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

74,120 miles

$32,995

Good Deal
Jacksonville, FL
37 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:
Jet Black
Transmission:
Automatic
Mileage:
74,120
Stock number:
26C478A
VIN:
3GCPDCED5NG664362

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

79,400 miles

$28,091

Good Deal
Jacksonville, FL
34 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:
Shadow Gray Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
79,400
Stock number:
KZ387181T
VIN:
1GCPYCEF5KZ387181

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

34,265 miles

$36,995

Great Deal
Jacksonville, FL
37 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:
Sterling Gray Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
34,265
Stock number:
26C275A
VIN:
3GCPDCEK7RG198311

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

15,144 miles

$40,593

Good Deal
Certified Pre-Owned
Jacksonville, FL
32 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:
15,144
Stock number:
313252A
VIN:
3GCPDCEKXRG256489

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

29,946 miles

$36,988

Good Deal
Saint Augustine, FL
3 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:
Black
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
29,946
Stock number:
DPG271429
VIN:
3GCPDCEK5PG271429

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,035 miles

$30,000

Good Deal
Daytona Beach, FL
50 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:
55,035
Stock number:
S080959R
VIN:
1GCPYCEF7KZ428801

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

34,593 miles

$36,500

Great Deal
Saint Augustine, FL
6 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:
34,593
Stock number:
254686A
VIN:
3GCPDCEK0RG198313

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

74,120 miles

$32,995

Good Deal
Jacksonville, FL
37 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:
Jet Black
Transmission:
Automatic
Mileage:
74,120
Stock number:
26C478A
VIN:
3GCPDCED5NG664362

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

3,601 miles

$41,978

Good Deal
Daytona Beach, FL
50 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:
3,601
Stock number:
265877A
VIN:
3GCPKCEK7SG250645

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,035 miles

$30,000

Good Deal
Daytona Beach, FL
50 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:
55,035
Stock number:
S080959R
VIN:
1GCPYCEF7KZ428801

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Florida
  6. / Saint Augustine
  • Chevrolet Silverado 1500 LT in Saint Augustine FL

  • Chevrolet Silverado 1500 RST in Saint Augustine FL

  • Chevrolet Silverado 1500 LTZ in Saint Augustine FL

  • Chevrolet Silverado 1500 LT Trail Boss in Saint Augustine FL

  • Chevrolet Silverado 1500 LT1 in Saint Augustine FL

  • Chevrolet Silverado 1500 Custom in Saint Augustine FL

  • Chevrolet Silverado 1500 High Country in Saint Augustine FL

  • Chevrolet Silverado 1500 Custom Trail Boss in Saint Augustine FL

  • Chevrolet Silverado 1500 Work Truck in Saint Augustine FL

  • Chevrolet Silverado 1500 in Jacksonville FL

  • Chevrolet Silverado 1500 in Daytona Beach FL

  • Chevrolet Silverado 1500 in Gainesville FL

  • Chevrolet Silverado 1500 in Ocala FL

  • Chevrolet Silverado 1500 in Lake City FL

  • Chevrolet Silverado 1500 in Leesburg FL

  • Chevrolet Silverado 1500 in Brunswick GA

  • Chevrolet Silverado 1500 in Orlando FL

  • Chevrolet Silverado 1500 in Titusville FL

  • Chevrolet Silverado 1500 in Saint Augustine FL

  • Old Chevy Trucks for Sale in Saint Augustine FL

  • Classic Muscle Cars for Sale in Saint Augustine FL

  • Chevrolet Trucks For Sale in Saint Augustine FL

  • Cheap Muscle Cars for Sale in Saint Augustine FL

  • Work Trucks for Sale in Saint Augustine FL

  • Reliable Cars For Sale in Saint Augustine FL

  • American Made Trucks For Sale in Saint Augustine FL

  • Best Pickup Trucks For Sale in Saint Augustine FL

  • Best Cars Under $5,000 For Sale in Saint Augustine FL

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Saint Augustine FL

  • 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

  • George Moore Chevrolet

  • Tom Gibbs Chevrolet, Inc.

  • Nimnicht Chevrolet

  • Beaver Chevrolet

  • Gordon Chevrolet

  • Garber Automall

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.