Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearFort Myers, FL
132 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Cherry Red Tintcoat
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 107,027
- Stock #:
- MZ235837
- VIN:
- 1GCPYCEF1MZ235837
Sponsored by Group 1 Chevrolet Estero Bay
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
107,027 mi
Estero, FL
15 mi away
Fair Deal
$27,640
- 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
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 22,101
- Stock #:
- M260783A
- VIN:
- 3GCPKCEK0SG331793
Sponsored Listing
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
22,101 mi
Tampa, FL
96 mi away
Fair Deal
$43,297
- 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:
- Red Hot
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 89,003
- Stock #:
- MG436124
- VIN:
- 3GCPYCEL8MG436124
Sponsored Listing
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
89,003 mi
Fort Myers, FL
3 mi away
Good Deal
$30,554
- 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:
- Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 48,518
- Stock #:
- 5153
- VIN:
- 3GCUDCED9PG302640
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
48,518 mi
Seffner, FL
98 mi away
Great Deal
$33,992
- 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:
- Cherry Red Tintcoat
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 107,027
- Stock #:
- MZ235837
- VIN:
- 1GCPYCEF1MZ235837
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
107,027 mi
Estero, FL
15 mi away
Fair Deal
$27,640
- 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:
- Slate Gray Metallic
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 14,105
- Stock #:
- P9991
- VIN:
- 3GCUKCED5SG215235
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
14,105 mi
Home delivery from Jacksonville, FL
Price includes $258 shipping
Fair Deal
$45,118
- 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:
- Black
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 85,183
- Stock #:
- TKE40312A
- VIN:
- 1GCPYCEL3MZ279358
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
85,183 mi
Home delivery from Delray Beach, FL
Price includes $330 shipping
Good Deal
$32,173
- 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:
- 5,703
- Stock #:
- 9217
- VIN:
- 3GCPKCEK9SG334188
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
5,703 mi
Home delivery from Excelsior Springs, MO
Price includes $2,036 shipping
Good Deal
$41,986
- 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:
- Dark Ash Metallic
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 15,155
- Stock #:
- 1T26421A
- VIN:
- 3GCPDCEKXRG445742
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
15,155 mi
Lake Wales, FL
90 mi away
Fair Deal
$41,994
- 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:
- 49,499
- Stock #:
- C10752A
- VIN:
- 1GCPYCEF4MZ371976
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
49,499 mi
Sarasota, FL
63 mi away
Fair Deal
$35,620
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Red Hot
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 49,453
- Stock #:
- ZC26344
- VIN:
- 1GCPYCEK2NZ120128
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
49,453 mi
Home delivery from Hicksville, OH
Price includes $1,284 shipping
Good Deal
$31,624
- 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:
- Red Hot
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 11,319
- Stock #:
- 260883A
- VIN:
- 3GCPKCEK1TG191626
Price drop
-$1,000
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
11,319 mi
Home delivery from Canfield, OH
Price includes $1,492 shipping
Good Deal
$43,891
$42,890
- 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:
- Silver
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 133,123
- Stock #:
- 374625
- VIN:
- 1GCRYCEF4KZ374625
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
133,123 mi
Brandon, FL
94 mi away
Great Deal
$19,985
- 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:
- Gray
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 59,206
- Stock #:
- CF18364
- VIN:
- 3GCPDCED8NG572405
New arrival
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
59,206 mi
Tampa, FL
96 mi away
Fair Deal
$37,288
- 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:
- Black
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 129,857
- Stock #:
- 119868
- VIN:
- 1GCPYCEL3NZ119868
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
129,857 mi
Home delivery from Orlando, FL
Price includes $194 shipping
Good Deal
$25,182
- 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:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 23,397
- Stock #:
- 303090
- VIN:
- 3GCPDCEK0PG303090
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
23,397 mi
Home delivery from Dallas, TX
Price includes $1,496 shipping
Fair Deal
$38,490
- 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:
- Red Hot
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 89,003
- Stock #:
- MG436124
- VIN:
- 3GCPYCEL8MG436124
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
89,003 mi
Fort Myers, FL
3 mi away
Good Deal
$30,554
- Year:
- 2024
- 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:
- 25 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 51,858
- Stock #:
- CT164172
- VIN:
- 3GCUDCE84RG164172
New arrival
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,858 mi
Home delivery from Coconut Creek, FL
Price includes $262 shipping
Great Deal
$37,222
- 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:
- Summit White
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 7,558
- Stock #:
- CP1616
- VIN:
- 3GCPDCEK6RG364740
Price drop
-$1,171
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
7,558 mi
Venice, FL
45 mi away
Fair Deal
$44,858
$43,687
- 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:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 141,315
- Stock #:
- 435347C
- VIN:
- 3GCPYCEF9MG435347
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
141,315 mi
Home delivery from Orlando, FL
Price includes $171 shipping
Great Deal
$20,451
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Red
- Fuel type:
- Diesel
- Interior color:
- Black
- Mileage:
- 110,590
- Stock #:
- 301317
- VIN:
- 3GCUDCE84PG301317
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
110,590 mi
Home delivery from Euless, TX
Price includes $1,512 shipping
Good Deal
$29,730
- 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:
- Summit White
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 89,269
- Stock #:
- 261114A
- VIN:
- 1GCPYCEHXMZ389870
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
89,269 mi
Home delivery from East Liverpool, OH
Price includes $2,919 shipping
Fair Deal
$29,817
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 60,075
- Stock #:
- STK126304
- VIN:
- 1GCPYCEK4NZ126304
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
60,075 mi
Home delivery from Westfield, IN
Price includes $959 shipping
Fair Deal
$32,443
- 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:
- Gray
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 59,206
- Stock #:
- CF18364
- VIN:
- 3GCPDCED8NG572405
New arrival
Sponsored Listing
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
59,206 mi
Tampa, FL
96 mi away
Fair Deal
$37,288
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Fort Myers, FL?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $26,702.40. The average price has decreased by -1.1% since last year. The 135 for sale near Fort Myers, FL on CarGurus, range from $20,123 to $66,909 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Fort Myers, FL have no reported accidents or damage?
121 out of 135 for sale near Fort Myers, FL have no reported accidents or damage.
What is the fuel economy of the Chevrolet Silverado 1500 Custom Trail Boss?
Depending on the engine and options, the Chevrolet Silverado 1500 Custom Trail Boss gets between 15 and 24 MPG (or EV battery range).
What fuel types are available?
Diesel, Flex Fuel Vehicle, Gasoline engines are available.
*CarGurus meticulously monitors the prices of millions of pre-owned vehicle listings, offering users precise and up-to-date market insights. Historical pricing data excludes any additional dealer fees as of May 3, 2026.
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