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

131 results
Windermere, FL
2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD HGreg.com Orlando

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,544 miles

$26,998

Great Deal
Orlando, FL
13 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

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
13 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

2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

75,894 miles

$33,999

Fair Deal
Lake Wales, FL
38 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:
Glacier Blue Metallic
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
75,894
Stock number:
3P2814
VIN:
3GCPDCEK3PG167361

Sponsored

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

23,336 miles

$40,991

Good Deal
Clermont, FL
8 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

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

88,211 miles

$23,498

Good Deal
Orlando, FL
13 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

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

123,205 miles

$21,495

Fair Deal
Dade City, FL
40 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:
Black
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
123,205
Stock number:
14883
VIN:
1GCRYCEF1KZ314883

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
13 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

32,473 miles

$33,300

Good Deal
Orlando, FL
9 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

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

7,500 miles

$41,988

Good Deal
Sanford, FL
27 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

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

96,887 miles

$31,000

Fair Deal
Winter Haven, FL
35 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

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  4. / Custom Trail Boss
  5. / Florida
  6. / Windermere
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