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

112 results

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

33,701 miles

$38,949

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:: Gray
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 33,701
Stock #:: L612605A
VIN:: 3GCPDCEKXRG188646

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2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

4,072 miles

$47,912

Fair Deal

$898/mo est.

Manufacturer certified

Venice, FL

11 mi away

Year:: 2025
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 355 hp 5.3L V8
Exterior color:: Cypress Gray
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 4,072
Stock #:: CP1526
VIN:: 3GCUKCED4SG352599

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

89,089 miles

$30,592

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:: Red
Combined gas mileage:: 15 MPG
Fuel type:: Gasoline
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 89,089
Stock #:: I160769
VIN:: 1GCPYCEF7MZ160769

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

111,467 miles

$23,991

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:: Blue
Combined gas mileage:: 16 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 111,467
Stock #:: 8063
VIN:: 1GCPYCEF5KZ254789

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

25,631 miles

$38,304

Fair Deal

$729/mo est.

Manufacturer certified

Venice, FL

11 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:: 25,631
Stock #:: C5148A
VIN:: 3GCPDCEK6PG168357

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

68,057 miles

$31,393

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:: White
Combined gas mileage:: 15 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 68,057
Stock #:: I114086A
VIN:: 3GCPYCEF4MG317691

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

49,080 miles

$35,250

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:: 49,080
Stock #:: M7558Z
VIN:: 3GCPDCEK9PG147650

Home delivery

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

18,798 miles

$36,342

Good Deal

$705/mo est.

Third-party certified

Home delivery from Orlando, FL

Price includes $345 shipping

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 (Steel Metallic)
Combined gas mileage:: 16 MPG
Fuel type:: Flex Fuel Vehicle
Interior color:: Jet Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 18,798
Stock #:: D29209B
VIN:: 3GCPYCEH2MG141340

2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

4,802 miles

$43,491

Year:: 2026
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 310 hp 2.7L I4
Exterior color:: Gray
Combined gas mileage:: 16 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 4,802
Stock #:: G281745A
VIN:: 3GCPKCEK7TG158470

2024 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

33,701 miles

$38,949

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:: Gray
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 33,701
Stock #:: L612605A
VIN:: 3GCPDCEKXRG188646

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Home delivery

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

70,478 miles

$36,019

Fair Deal

$686/mo est.

Home delivery from Houston, TX

Price includes $1,020 shipping

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:: Dark Ash Metallic
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Gray
Transmission:: Automatic
Mileage:: 70,478
Stock #:: 189356
VIN:: 3GCUDCED4PG189356

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Home delivery

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

42,179 miles

$35,454

Fair Deal

$687/mo est.

Third-party certified

Home delivery from Lake Worth, FL

Price includes $459 shipping

Year:: 2022
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Exterior color:: Northsky Blue Metallic
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 42,179
Stock #:: L26040450T1
VIN:: 3GCPYCEK4NG106246

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

89,089 miles

$30,592

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:: Red
Combined gas mileage:: 15 MPG
Fuel type:: Gasoline
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 89,089
Stock #:: I160769
VIN:: 1GCPYCEF7MZ160769

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2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

9,604 miles

$39,999

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:: Sterling Gray Metallic
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 9,604
Stock #:: P0578
VIN:: 3GCPKCEK7SG305594

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2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,130 miles

$32,495

Fair Deal

$636/mo est.

Manufacturer certified

Brooksville, FL

93 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:: Black
Combined gas mileage:: 16 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 59,130
Stock #:: LZ250061
VIN:: 1GCPYCEFXLZ250061

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2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

87,697 miles

$26,555

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:: Cajun Red Tintcoat
Combined gas mileage:: 16 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 87,697
Stock #:: P263252
VIN:: 1GCPYCEF5LZ263252

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

81,650 miles

$31,797

Fair Deal

$617/mo est.

Store transfer to Bradenton, FL

19 mi awayPrice includes $799 store transfer

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:: White
Combined gas mileage:: 15 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 81,650
Stock #:: 28290621
VIN:: 3GCPYCEF3MG249383

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Home delivery

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

69,169 miles

$34,046

Fair Deal

$661/mo est.

Home delivery from Louisville, TN

Price includes $1,087 shipping

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:: 15 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 69,169
Stock #:: MD2611
VIN:: 1GCPYCEF8MZ358258

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Home delivery

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

12,642 miles

$45,944

Fair Deal

$861/mo est.

Home delivery from Deland, FL

Price includes $256 shipping

Year:: 2025
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
Interior color:: Black
Transmission:: Automatic
Mileage:: 12,642
Stock #:: G222732P
VIN:: 3GCUKCEDXSG222732

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

42,631 miles

$38,297

Fair Deal

$743/mo est.

Store transfer to Bradenton, FL

19 mi awayPrice includes $299 store transfer

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:: Silver
Combined gas mileage:: 17 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 42,631
Stock #:: 28557776
VIN:: 1GCPYCELXMZ375617

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2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

66,745 miles

$33,878

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:: Gray
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 66,745
Stock #:: STK163303
VIN:: 3GCUDCED7PG163303

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Home delivery

2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

1,008 miles

$45,244

Fair Deal

$845/mo est.

Home delivery from Deland, FL

Price includes $256 shipping

Year:: 2026
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:: 16 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 1,008
Stock #:: G172103T
VIN:: 3GCPKCEK6TG172103

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Home delivery

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

78,225 miles

$28,444

Fair Deal

$557/mo est.

Home delivery from Omaha, NE

Price includes $1,852 shipping

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
Combined gas mileage:: 16 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 78,225
Stock #:: 20067355
VIN:: 1GCPYCEF4KZ378634

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2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

7,726 miles

$49,299

Year:: 2026
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:: 22 MPG
Fuel type:: Diesel
Interior color:: Black
Transmission:: Automatic
Mileage:: 7,726
Stock #:: 4602407A
VIN:: 3GCUKCE87TG121328

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

2024 Chevrolet Silverado 1500

$38,949

2025 Chevrolet Silverado 1500

$47,912

2021 Chevrolet Silverado 1500

$30,592

2019 Chevrolet Silverado 1500

$23,991

2023 Chevrolet Silverado 1500

$38,304

2021 Chevrolet Silverado 1500

$31,393

2023 Chevrolet Silverado 1500

$35,250

2021 Chevrolet Silverado 1500

$36,342

2026 Chevrolet Silverado 1500

$43,491

2024 Chevrolet Silverado 1500

$38,949

2023 Chevrolet Silverado 1500

$36,019

2022 Chevrolet Silverado 1500

$35,454

2021 Chevrolet Silverado 1500

$30,592

2025 Chevrolet Silverado 1500

$39,999

2020 Chevrolet Silverado 1500

$32,495

2020 Chevrolet Silverado 1500

$26,555

2021 Chevrolet Silverado 1500

$31,797

2021 Chevrolet Silverado 1500

$34,046

2025 Chevrolet Silverado 1500

$45,944

2021 Chevrolet Silverado 1500

$38,297

2023 Chevrolet Silverado 1500

$33,878

2026 Chevrolet Silverado 1500

$45,244

2019 Chevrolet Silverado 1500

$28,444

2026 Chevrolet Silverado 1500

$49,299

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