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 Orlando, FL

143 results
Orlando, FL
2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Starling Chevrolet GMC

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

64,264 miles

$31,999

Fair Deal
Saint Cloud, FL
22 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Gray (Satin Steel Metallic)
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
64,264
Stock number:
123629T
VIN:
3GCPYCEK6NG123629

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,544 miles

$27,998

Great Deal
Orlando, FL
7 mi away
Year:
2022
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:
Automatic
Mileage:
59,544
Stock number:
Z129755
VIN:
1GCPYCEK8NZ129755

Sponsored

2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

3,482 miles

$42,997

Good Deal
Orlando, FL
3 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:
Slate Gray Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
3,482
Stock number:
SG168515
VIN:
3GCPKCEK0SG168515

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

67,324 miles

$29,999

Good Deal
Certified Pre-Owned
Lake Wales, FL
45 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:
67,324
Stock number:
6T25497A
VIN:
1GCPYCEK7NZ105933

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

72,546 miles

$25,998

Great Deal
Orlando, FL
7 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
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
72,546
Stock number:
G151037
VIN:
3GCPYCEF0LG151037

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,544 miles

$27,998

Great Deal
Orlando, FL
7 mi away
Year:
2022
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:
Automatic
Mileage:
59,544
Stock number:
Z129755
VIN:
1GCPYCEK8NZ129755

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

125,492 miles

$21,868

Great Deal
Melbourne, FL
45 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:
125,492
Stock number:
P1327
VIN:
1GCPYCEF6KZ377520

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

64,264 miles

$31,999

Fair Deal
Saint Cloud, FL
22 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Gray (Satin Steel Metallic)
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
64,264
Stock number:
123629T
VIN:
3GCPYCEK6NG123629

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

81,664 miles

$26,298

Great Deal
Orlando, FL
7 mi away
Year:
2021
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:
Gray
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
Automatic
Mileage:
81,664
Stock number:
Z243264
VIN:
1GCPYCEH7MZ243264

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

76,923 miles

$27,599

Fair Deal
Lake Wales, FL
45 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:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
76,923
Stock number:
2S25609C
VIN:
1GCRYCEF1KZ198083

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,199 miles

$37,992

Fair Deal
Clermont, FL
18 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:
Red Hot
Fuel type:
Gasoline
Mileage:
55,199
Stock number:
TPG304807
VIN:
3GCUDCED7PG304807

Sponsored

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

  • Chevrolet Silverado 1500 LT in Orlando FL

  • Chevrolet Silverado 1500 RST in Orlando FL

  • Chevrolet Silverado 1500 LTZ in Orlando FL

  • Chevrolet Silverado 1500 LT Trail Boss in Orlando FL

  • Chevrolet Silverado 1500 LT1 in Orlando FL

  • Chevrolet Silverado 1500 Custom in Orlando FL

  • Chevrolet Silverado 1500 High Country in Orlando FL

  • Chevrolet Silverado 1500 Custom Trail Boss in Orlando FL

  • Chevrolet Silverado 1500 Work Truck in Orlando FL

  • Chevrolet Silverado 1500 in Titusville FL

  • Chevrolet Silverado 1500 in Leesburg FL

  • Chevrolet Silverado 1500 in Daytona Beach FL

  • Chevrolet Silverado 1500 in Lakeland FL

  • Chevrolet Silverado 1500 in Melbourne FL

  • Chevrolet Silverado 1500 in Brooksville FL

  • Chevrolet Silverado 1500 in Ocala FL

  • Chevrolet Silverado 1500 in Sebring FL

  • Chevrolet Silverado 1500 in Tampa FL

  • Chevrolet Silverado 1500 in Orlando FL

  • Old Chevy Trucks for Sale in Orlando FL

  • Classic Muscle Cars for Sale in Orlando FL

  • Chevrolet Trucks For Sale in Orlando FL

  • Cheap Muscle Cars for Sale in Orlando FL

  • Work Trucks for Sale in Orlando FL

  • Reliable Cars For Sale in Orlando FL

  • American Made Trucks For Sale in Orlando FL

  • Best Pickup Trucks For Sale in Orlando FL

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

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Orlando 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

  • Starling Chevrolet of Orlando

  • Starling Chevrolet GMC

  • Don Mealey Chevrolet

  • AutoNation Chevrolet Airport

  • Dyer Chevrolet Lake Wales

  • Regal Chevrolet

  • Carroll Chevrolet

  • Carl Black of Orlando

  • Vann Gannaway Chevrolet

  • Jon Hall Chevrolet, Inc.

  • Cecil Clark Chevrolet

  • Seminole 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

© 2025 CarGurus, Inc., All Rights Reserved.