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Used Chevrolet Silverado 1500 LT Trail Boss for Sale near Fort Myers, FL

278 results
Fort Myers, FL
2024 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD Nissan of Cape Coral

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

53,857 miles

$45,888

Fair Deal
Cape Coral, FL
6 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:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
53,857
Stock number:
CP3289
VIN:
3GCUDFED5RG104528

Sponsored

2020 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

70,424 miles

$32,888

Good Deal
Tampa, FL
96 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:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
70,424
Stock number:
C262028A
VIN:
3GCPYFED6LG356247

Sponsored

2022 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

55,623 miles

$35,894

Good Deal
Certified Pre-Owned
Lakeland, FL
97 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Black
Interior color:
Black
Transmission:
Automatic
Mileage:
55,623
Stock number:
KP14272
VIN:
3GCPYFEL9NG195158

Sponsored

2023 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

47,375 miles

$39,998

Great Deal
Naples, FL
29 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:
White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
47,375
Stock number:
G286639
VIN:
3GCUDFED6PG286639

2022 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

74,803 miles

$34,888

Great Deal
Certified Pre-Owned
Tampa, FL
96 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:
Non-Color
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
74,803
Stock number:
C261719A
VIN:
3GCPYFED7NG207641

2022 Chevrolet Silverado 1500 LT Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

55,623 miles

$35,894

Good Deal
Certified Pre-Owned
Lakeland, FL
97 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Black
Interior color:
Black
Transmission:
Automatic
Mileage:
55,623
Stock number:
KP14272
VIN:
3GCPYFEL9NG195158

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

9,946 miles

$50,842

Good Deal
Certified Pre-Owned
Punta Gorda, FL
24 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:
White (Iridescent Pearl Tricoat)
Combined gas mileage:
25 MPG
Fuel type:
Diesel
Interior color:
Gideon/Very Dark Atmosphere
Transmission:
Automatic
Mileage:
9,946
Stock number:
G123656A
VIN:
3GCUDFE82RG442102

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2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

104,058 miles

$24,850

Great Deal
Venice, FL
48 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:
104,058
Stock number:
MZ302700
VIN:
1GCPYFED3MZ302700

Preparing for a close up...

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2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

106,123 miles

$24,993

Great Deal
South Venice, 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:
Northsky Blue Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
106,123
Stock number:
MS160A
VIN:
1GCPYFED6KZ346994

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2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

62,530 miles

$35,683

Great Deal
Bartow, FL
87 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:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
62,530
Stock number:
R25173
VIN:
3GCUDFED6PG313774

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2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

19,520 miles

$41,997

Fair Deal
Store transfer to Fort Myers, FL
2,586 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...

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2020 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

86,015 miles

$29,861

Great Deal
Tampa, FL
96 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:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
86,015
Stock number:
T1637A
VIN:
3GCPYFED3LG372485

Preparing for a close up...

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2022 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

43,661 miles

$39,993

Good Deal
Lakeland, FL
97 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Black
Interior color:
Black
Transmission:
Automatic
Mileage:
43,661
Stock number:
25C503A
VIN:
1GCPYFEL7NZ150283

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

44,970 miles

$39,793

Great Deal
Tampa, FL
96 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:
Radiant Red Tintcoat
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
44,970
Stock number:
T1021A
VIN:
3GCUDFED9PG188804

Preparing for a close up...

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2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

86,178 miles

$38,675

Good Deal
Plant City, FL
98 mi away
Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Sterling Gray Metallic
Combined gas mileage:
24 MPG
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
86,178
Stock number:
PG308117
VIN:
3GCUDFE87PG308117

Preparing for a close up...

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2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

72,584 miles

$35,988

Fair Deal
Tampa, FL
96 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:
Brown
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
72,584
Stock number:
CF17874A
VIN:
3GCPYFED5MG425141

Sponsored

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  5. / Florida
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