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 LT Trail Boss for Sale near Winter Springs, FL

268 results
Winter Springs, FL
2023 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD AutoNation Chevrolet West Colonial

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

93,433 miles

$32,997

Fair Deal
Orlando, FL
13 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
Transmission:
8-Speed Automatic
Mileage:
93,433
Stock number:
PG303985
VIN:
3GCPDFEK8PG303985

Sponsored

2019 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

92,018 miles

$30,495

Fair Deal
Titusville, FL
29 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:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
92,018
Stock number:
198874T
VIN:
1GCPYFED0KZ198874

Sponsored

2022 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

19,810 miles

$37,990

Great Deal
St Cloud, FL
30 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Black
Mileage:
19,810
Stock number:
196738
VIN:
1GCPYFED9NZ196738

Sponsored

2023 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

10,083 miles

$44,988

Fair Deal
Certified Pre-Owned
Leesburg, FL
34 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:
Dark Ash Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Mileage:
10,083
Stock number:
P25067
VIN:
3GCPDFEK2PG249776

2020 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

87,057 miles

$29,188

Great Deal
Deland, FL
21 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:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
87,057
Stock number:
Z150393T
VIN:
1GCPYFED6LZ150393

2021 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

53,062 miles

$36,800

Fair Deal
New Smyrna Beach, FL
30 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
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
53,062
Stock number:
G384752A
VIN:
1GCPYFED0MZ404729

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

18,359 miles

$41,999

Good Deal
Winter Park, FL
5 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:
Gray (Satin Steel Metallic)
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
18,359
Stock number:
MZ313974
VIN:
1GCPYFEL8MZ313974

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

19,810 miles

$37,990

Great Deal
St Cloud, FL
30 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Black
Mileage:
19,810
Stock number:
196738
VIN:
1GCPYFED9NZ196738

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

86,536 miles

$28,978

Great Deal
Daytona Beach, FL
39 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:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
86,536
Stock number:
265580A
VIN:
1GCPYFED4KZ424463

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

97,015 miles

$33,440

Great Deal
Orlando, FL
23 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:
Sterling Gray Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
97,015
Stock number:
332215T
VIN:
3GCUDFEDXPG332215

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

92,018 miles

$30,495

Fair Deal
Titusville, FL
29 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:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
92,018
Stock number:
198874T
VIN:
1GCPYFED0KZ198874

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

19,520 miles

$40,997

Good Deal
Store transfer to Sanford, FL
2,521 mi away • Price includes $1,999 shipping Price includes $1,999 shipping
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Blue
Interior color:
Black
Transmission:
Automatic
Mileage:
19,520
Stock number:
26433898
VIN:
1GCPYFEL0NZ228094

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

48,763 miles

$40,000

Good Deal
Daytona Beach, FL
39 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:
Dark Ash Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
48,763
Stock number:
X291933A
VIN:
3GCUDFED8NG658723

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

63,982 miles

$41,965

Great Deal
Certified Pre-Owned
Daytona Beach, FL
39 mi away
Year:
2024
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:
25 MPG
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
63,982
Stock number:
266003A
VIN:
3GCUDFE83RG144268

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

54,752 miles

$37,471

Good Deal
Daytona Beach, FL
38 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:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
54,752
Stock number:
ZZ405813
VIN:
1GCPYFEL6MZ405813

Sponsored

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

  • Chevrolet Silverado 1500 LT in Winter Springs FL

  • Chevrolet Silverado 1500 RST in Winter Springs FL

  • Chevrolet Silverado 1500 LTZ in Winter Springs FL

  • Chevrolet Silverado 1500 LT Trail Boss in Winter Springs FL

  • Chevrolet Silverado 1500 LT1 in Winter Springs FL

  • Chevrolet Silverado 1500 Custom in Winter Springs FL

  • Chevrolet Silverado 1500 High Country in Winter Springs FL

  • Chevrolet Silverado 1500 Custom Trail Boss in Winter Springs FL

  • Chevrolet Silverado 1500 Work Truck in Winter Springs FL

  • Chevrolet Silverado 1500 in Orlando FL

  • Chevrolet Silverado 1500 in Titusville FL

  • Chevrolet Silverado 1500 in Daytona Beach FL

  • Chevrolet Silverado 1500 in Leesburg FL

  • Chevrolet Silverado 1500 in Melbourne FL

  • Chevrolet Silverado 1500 in Lakeland FL

  • Chevrolet Silverado 1500 in Ocala FL

  • Chevrolet Silverado 1500 in Brooksville FL

  • Chevrolet Silverado 1500 in Crystal River FL

  • Chevrolet Silverado 1500 in Winter Springs FL

  • Old Chevy Trucks for Sale in Winter Springs FL

  • Classic Muscle Cars for Sale in Winter Springs FL

  • Chevrolet Trucks For Sale in Winter Springs FL

  • Cheap Muscle Cars for Sale in Winter Springs FL

  • Work Trucks for Sale in Winter Springs FL

  • Reliable Cars For Sale in Winter Springs FL

  • American Made Trucks For Sale in Winter Springs FL

  • Best Pickup Trucks For Sale in Winter Springs FL

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

  • 2019 Chevrolet Silverado 1500 LT Trail Boss in Winter 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

  • AutoNation Chevrolet West Colonial

  • Starling Chevrolet GMC

  • Don Mealey Chevrolet

  • Carroll Chevrolet

  • AutoNation Chevrolet Airport

  • Carl Black of Orlando

  • Vann Gannaway Chevrolet

  • Jon Hall Chevrolet, Inc.

  • Cecil Clark Chevrolet

  • Seminole Chevrolet

  • 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.