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Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Winter Park, FL

129 results
Winter Park, FL
2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Starling Chevrolet of Orlando

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

29,676 miles

$36,449

Good Deal
Orlando, FL
16 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:
29,676
Stock number:
672607T
VIN:
3GCPDCED5NG672607

Sponsored

2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

5,885 miles

$43,799

Fair Deal
Certified Pre-Owned
Mount Dora, FL
25 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:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
5,885
Stock number:
T25412A
VIN:
3GCPKCEK0SG323144

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,544 miles

$27,382

Great Deal
Orlando, FL
10 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

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

12,753 miles

$43,899

Good Deal
Certified Pre-Owned
Titusville, FL
32 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:
Slate Gray Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
12,753
Stock number:
283172E
VIN:
3GCUDCED0RG283172

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

52,534 miles

$33,999

Fair Deal
Certified Pre-Owned
Lake Wales, FL
49 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:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
52,534
Stock number:
3T26219A
VIN:
3GCPDCEK0NG518272

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

72,546 miles

$25,390

Great Deal
Orlando, FL
10 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

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

101,246 miles

$25,999

Good Deal
Lake Wales, FL
49 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 (Satin Steel Metallic)
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
101,246
Stock number:
5K26045B
VIN:
1GCPYCEF5LZ143001

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,035 miles

$29,700

Good Deal
Daytona Beach, FL
46 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

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

125,492 miles

$21,000

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

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

18,090 miles

$36,888

Great Deal
Longwood, FL
7 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:
Red Hot
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
18,090
Stock number:
NB340790
VIN:
3GCPDCEK4PG340790

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Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,544 miles

$27,382

Great Deal
Orlando, FL
10 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

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

89,192 miles

$29,490

Fair Deal
Orlando, FL
14 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
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Transmission:
6-Speed Automatic Overdrive
Mileage:
89,192
Stock number:
141396
VIN:
3GCPYCEH7MG141396

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

89,192 miles

$29,490

Fair Deal
Orlando, FL
14 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
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Transmission:
6-Speed Automatic Overdrive
Mileage:
89,192
Stock number:
141396
VIN:
3GCPYCEH7MG141396

Sponsored

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  4. / Custom Trail Boss
  5. / Florida
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