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 Altamonte Springs, FL

133 results
Altamonte Springs, FL
2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Chevrolet Center Incorporated

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

96,887 miles

$31,000

Fair Deal
Winter Haven, FL
49 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:
Jet Black
Transmission:
Automatic
Mileage:
96,887
Stock number:
261481
VIN:
3GCPYCEL7NG112552

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

88,211 miles

$23,498

Good Deal
Orlando, FL
15 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:
Gray
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
88,211
Stock number:
Z388924
VIN:
1GCRYCEF7KZ388924

Sponsored

2026 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

8,609 miles

$52,895

Fair Deal
Certified Pre-Owned
Orlando, FL
20 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:
Black
Fuel type:
Diesel
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
8,609
Stock number:
104237T
VIN:
3GCUKCE87TG104237

Sponsored

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,544 miles

$26,998

Great Deal
Orlando, FL
15 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

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

7,500 miles

$41,988

Good Deal
Sanford, FL
12 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:
Cypress Gray
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black, Cloth seat trim
Transmission:
Automatic
Mileage:
7,500
Stock number:
T1100547A
VIN:
3GCPKCEK8SG258138

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

32,473 miles

$33,300

Good Deal
Orlando, FL
8 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:
Northsky Blue Metallic
Fuel type:
Flex Fuel Vehicle
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
32,473
Stock number:
MZ186231
VIN:
1GCPYCEH2MZ186231

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

88,211 miles

$23,498

Good Deal
Orlando, FL
15 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:
Gray
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
88,211
Stock number:
Z388924
VIN:
1GCRYCEF7KZ388924

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
44 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

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

23,336 miles

$41,491

Fair Deal
Clermont, FL
17 mi away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Sterling Gray Metallic
Fuel type:
Gasoline
Mileage:
23,336
Stock number:
TRG393031
VIN:
3GCUDCED6RG393031

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,544 miles

$26,998

Great Deal
Orlando, FL
15 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

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

  • Chevrolet Silverado 1500 LT in Altamonte Springs FL

  • Chevrolet Silverado 1500 RST in Altamonte Springs FL

  • Chevrolet Silverado 1500 LTZ in Altamonte Springs FL

  • Chevrolet Silverado 1500 LT Trail Boss in Altamonte Springs FL

  • Chevrolet Silverado 1500 LT1 in Altamonte Springs FL

  • Chevrolet Silverado 1500 High Country in Altamonte Springs FL

  • Chevrolet Silverado 1500 Custom in Altamonte Springs FL

  • Chevrolet Silverado 1500 Custom Trail Boss in Altamonte Springs FL

  • Chevrolet Silverado 1500 Work Truck in Altamonte Springs FL

  • Chevrolet Silverado 1500 in Orlando FL

  • Chevrolet Silverado 1500 in Leesburg FL

  • Chevrolet Silverado 1500 in Titusville FL

  • Chevrolet Silverado 1500 in Daytona Beach FL

  • Chevrolet Silverado 1500 in Lakeland FL

  • Chevrolet Silverado 1500 in Ocala FL

  • Chevrolet Silverado 1500 in Brooksville FL

  • Chevrolet Silverado 1500 in Melbourne FL

  • Chevrolet Silverado 1500 in Crystal River FL

  • Chevrolet Silverado 1500 in Altamonte Springs FL

  • Old Chevy Trucks for Sale in Altamonte Springs FL

  • Classic Muscle Cars for Sale in Altamonte Springs FL

  • Chevrolet Trucks For Sale in Altamonte Springs FL

  • Cheap Muscle Cars for Sale in Altamonte Springs FL

  • Work Trucks for Sale in Altamonte Springs FL

  • Reliable Cars For Sale in Altamonte Springs FL

  • American Made Trucks For Sale in Altamonte Springs FL

  • Best Pickup Trucks For Sale in Altamonte Springs FL

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

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Altamonte Springs 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

  • AutoNation Chevrolet West Colonial

  • Carroll Chevrolet

  • Don Mealey Chevrolet

  • AutoNation Chevrolet Airport

  • Carl Black of Orlando

  • Vann Gannaway Chevrolet

  • Seminole Chevrolet

  • Jon Hall Chevrolet, Inc.

  • George Nahas 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.