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 Crestview, FL

143 results
Crestview, FL
2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD AutoNation Ford Mobile

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

27,261 miles

$37,230

Great Deal
Mobile, AL
91 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:
Red Hot
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
27,261
Stock number:
SG316935
VIN:
3GCPKCEK7SG316935

Sponsored

2026 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

7,161 miles

$52,894

Fair Deal
Brewton, AL
37 mi away
Year:
2026
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Sterling Gray Metallic
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
7,161
Stock number:
15164C
VIN:
3GCUKCE87TG104688

Sponsored

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

134,229 miles

$25,500

Great Deal
Mobile, AL
91 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:
Shadow Gray Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
134,229
Stock number:
V01591T
VIN:
1GCPYCEL2NZ201591

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

27,261 miles

$37,230

Great Deal
Mobile, AL
91 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:
Red Hot
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
27,261
Stock number:
SG316935
VIN:
3GCPKCEK7SG316935

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

48,585 miles

$32,550

Fair Deal
Fort Walton Beach, FL
22 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:
Northsky Blue Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
48,585
Stock number:
12P247857
VIN:
3GCPYCEF5KG247857

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / Florida
  6. / Crestview

  • Chevrolet Silverado 1500 LT in Crestview FL

  • Chevrolet Silverado 1500 RST in Crestview FL

  • Chevrolet Silverado 1500 LTZ in Crestview FL

  • Chevrolet Silverado 1500 LT Trail Boss in Crestview FL

  • Chevrolet Silverado 1500 LT1 in Crestview FL

  • Chevrolet Silverado 1500 High Country in Crestview FL

  • Chevrolet Silverado 1500 Custom in Crestview FL

  • Chevrolet Silverado 1500 Custom Trail Boss in Crestview FL

  • Chevrolet Silverado 1500 Work Truck in Crestview FL

  • Chevrolet Silverado 1500 in Fort Walton Beach FL

  • Chevrolet Silverado 1500 in Pensacola FL

  • Chevrolet Silverado 1500 in Atmore AL

  • Chevrolet Silverado 1500 in Panama City FL

  • Chevrolet Silverado 1500 in Monroeville AL

  • Chevrolet Silverado 1500 in Dothan AL

  • Chevrolet Silverado 1500 in Marianna FL

  • Chevrolet Silverado 1500 in Mobile AL

  • Chevrolet Silverado 1500 in Montgomery AL

  • Chevrolet Silverado 1500 in Crestview FL

  • Old Chevy Trucks for Sale in Crestview FL

  • Classic Muscle Cars for Sale in Crestview FL

  • Chevrolet Trucks For Sale in Crestview FL

  • Cheap Muscle Cars for Sale in Crestview FL

  • Work Trucks for Sale in Crestview FL

  • Reliable Cars For Sale in Crestview FL

  • American Made Trucks For Sale in Crestview FL

  • Best Pickup Trucks For Sale in Crestview FL

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

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Crestview 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

  • Peach Chevrolet Buick GMC

  • J M Jackson Chevrolet Buick

  • Pete Moore 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.