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

129 results
Eustis, FL

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2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

53,074 miles

$35,440

Fair Deal
Orlando, FL
37 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:
Silver Ice Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
53,074
Stock number:
535854T
VIN:
3GCPDCED6NG535854

Sponsored

2025 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

27,261 miles

$36,997

Good Deal
Orlando, FL
26 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:
Red Hot
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
27,261
Stock number:
SG316935
VIN:
3GCPKCEK7SG316935

Sponsored

2024 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

51,267 miles

$34,399

Good Deal
Orlando, FL
32 mi away
Year:
2024
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
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
51,267
Stock number:
RG191331
VIN:
3GCPDCEK0RG191331

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

108,208 miles

$23,586

Great Deal
Dade City, FL
47 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:
108,208
Stock number:
A531106A
VIN:
3GCPYCEF0KG304160

2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

72,546 miles

$25,498

Great Deal
Orlando, FL
35 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

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2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

55,035 miles

$30,000

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

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2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

52,262 miles

$36,982

Good Deal
Ocala, FL
36 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:
52,262
Stock number:
A094456A
VIN:
3GCUDCED2PG279444

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2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,544 miles

$27,498

Great Deal
Orlando, FL
35 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

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2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

18,090 miles

$36,888

Great Deal
Longwood, FL
24 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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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

89,192 miles

$29,490

Fair Deal
Orlando, FL
35 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

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2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

3,601 miles

$41,978

Good Deal
Daytona Beach, FL
46 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

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

81,664 miles

$25,998

Great Deal
Orlando, FL
35 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:
Gray
Combined gas mileage:
16 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
Automatic
Mileage:
81,664
Stock number:
Z243264
VIN:
1GCPYCEH7MZ243264

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2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

123,205 miles

$21,495

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

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2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

12,587 miles

$46,999

Fair Deal
Davenport, FL
44 mi away
Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Cypress
Combined gas mileage:
23 MPG
Fuel type:
Diesel
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
12,587
Stock number:
U561784A
VIN:
3GCUKCE8XSG242451

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2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

52,262 miles

$36,982

Good Deal
Ocala, FL
36 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:
52,262
Stock number:
A094456A
VIN:
3GCUDCED2PG279444

Sponsored

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