Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Windsor, ON
2,243 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2020
- 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:
- Red Hot
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 84,961
- Stock #:
- C630228A
- VIN:
- 1GCPYCEH5LZ139161
Price drop
-$1,369
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
84,961 mi
Dade City, FL
1 mi away
Good Deal
$27,817
$26,448
- 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:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 45,061
- Stock #:
- TU114164
- VIN:
- 3GCPKCEK2SG114164
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
45,061 mi
Round Rock, TX
1 mi away
Good Deal
$36,724
- 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:
- 10,078
- Stock #:
- TG422805A
- VIN:
- 3GCPKCEK6TG128831
New arrival
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
10,078 mi
Glenpool, OK
1 mi away
Good Deal
$41,476
- 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:
- Red
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 129,452
- VIN:
- 1GCPYCEF2LZ162069
New arrival
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
129,452 mi
Detroit Lakes, MN
1 mi away
Good Deal
$21,999
- 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
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 64,213
- Stock #:
- B7006B
- VIN:
- 1GCRYCEF1KZ343008
New arrival
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
64,213 mi
Bourbonnais, IL
1 mi away
Fair Deal
$29,696
- 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:
- 46,449
- Stock #:
- 123346
- VIN:
- 3GCPDCED8NG672391
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
46,449 mi
Woods Cross, UT
1 mi away
Great Deal
$32,500
- 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:
- Summit White
- Fuel type:
- Gasoline
- Interior color:
- Cloth
- Mileage:
- 10,292
- Stock #:
- H211261
- VIN:
- 3GCUKCED8SG211261
New arrival
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
10,292 mi
Graniteville, SC
1 mi away
Fair Deal
$46,373
- 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:
- Black
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 106,192
- Stock #:
- MP7430A
- VIN:
- 1GCPYCEF7MZ281592
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
106,192 mi
Northglenn, CO
1 mi away
Good Deal
$27,326
- 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
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Mileage:
- 2,601
- Stock #:
- U13095
- VIN:
- 3GCPKCEK1SG233162
New arrival
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
2,601 mi
Waipahu, HI
1 mi away
Great Deal
$45,772
- 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:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 19,487
- Stock #:
- 26799A
- VIN:
- 3GCPKCEK3SG312753
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
19,487 mi
Thompsontown, PA
1 mi away
Good Deal
$40,837
- 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:
- Summit White
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 59,020
- Stock #:
- GG26312A
- VIN:
- 3GCPDCEK8PG279279
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
59,020 mi
Carson City, NV
1 mi away
Good Deal
$36,726
- 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
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 153,098
- Stock #:
- F2558197M
- VIN:
- 1GCRYCEF6KZ295103
Price drop
-$361
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
153,098 mi
Watertown, CT
1 mi away
Good Deal
$17,648
$17,287
- 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:
- Automatic
- Mileage:
- 108,735
- Stock #:
- PM31343
- VIN:
- 1GCPYCEF5LZ274946
Price drop
-$2,170
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
108,735 mi
Kokomo, IN
1 mi away
Great Deal
$26,702
$24,532
- Year:
- 2019
- 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:
- Red Hot
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 86,986
- Stock #:
- YP716
- VIN:
- 1GCPYCEH4KZ399582
Price drop
-$2,762
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
86,986 mi
Danville, IL
1 mi away
Good Deal
$28,607
$25,845
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 277 hp 3L I6 Diesel
- Exterior color:
- Sand Dune Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 54,240
- Stock #:
- C16139
- VIN:
- 3GCUDCET0NG535858
Price drop
-$1,500
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
54,240 mi
Dayton, OH
1 mi away
Good Deal
$35,893
$34,393
- 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:
- Silver
- Fuel type:
- Gasoline
- Mileage:
- 83,680
- Stock #:
- 25G047B
- VIN:
- 3GCPYCEF0LG109712
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
83,680 mi
Karnes City, TX
1 mi away
Great Deal
$27,719
- 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
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 90,908
- Stock #:
- 4746H
- VIN:
- 1GCPYCEF9KZ177084
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
90,908 mi
Pekin, IL
1 mi away
Fair Deal
$27,996
- 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 (Satin Steel Metallic)
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 49,279
- Stock #:
- WT60309A
- VIN:
- 1GCPYCEH7MZ404924
New arrival
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
49,279 mi
Saint Albans, WV
1 mi away
Good Deal
$32,053
- 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
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 83,964
- Stock #:
- C26460A
- VIN:
- 1GCPYCEF2MZ364900
Price drop
-$972
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
83,964 mi
Avon, IN
1 mi away
Great Deal
$28,624
$27,914
- 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:
- 62,373
- Stock #:
- NG558202A
- VIN:
- 3GCPDCED1NG558202
Price drop
-$1,310
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
62,373 mi
Miami, OK
1 mi away
Good Deal
$35,427
$34,117
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Black
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 60,985
- Stock #:
- F0140AE
- VIN:
- 1GCPYCEK5NZ128658
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
60,985 mi
Columbiana, OH
1 mi away
Good Deal
$31,410
- 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:
- 7,734
- Stock #:
- BB2065
- VIN:
- 3GCUKCED9SG279147
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
7,734 mi
Boise, ID
1 mi away
Good Deal
$43,646
- 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:
- White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 55,264
- Stock #:
- A628177C
- VIN:
- 3GCUDCED0RG145647
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
55,264 mi
Tampa, FL
1 mi away
Great Deal
$36,292
- 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:
- 86,352
- Stock #:
- 9010A
- VIN:
- 3GCPYCEL9NG144497
Price drop
-$1,705
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
86,352 mi
Brewton, AL
1 mi away
Good Deal
$34,311
$32,606
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Windsor, ON?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $26,372.53. The average price has decreased by -2.8% since last year. The 174 for sale near Windsor, ON on CarGurus, range from $20,504 to $65,094 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Windsor, ON have no reported accidents or damage?
148 out of 174 for sale near Windsor, ON 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/MPGe.
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.
Relevant articles
CarGurus Editorial Team
Best Cars for New Parents
Discover the best family cars for first-time parents in 2025, accounting for door access, car seat compatibility, and other real-world considerations new parents will want to keep in mind.
Drew Johnson
The Cheapest New Trucks on Sale in 2026
Is there such a thing as a cheap new truck any more? Absolutely! Here's our expert guide to the top 10 cheapest new trucks on sale.
CarGurus Editorial Team
The Best Gas Mileage Trucks of 2026
No one wants to cover unnecessary fuel expenses, particularly when operating a business. Here are the top 9 pickup trucks in the US market with the best fuel efficiency.
Chevrolet Silverado 1500 LT in Windsor ONChevrolet Silverado 1500 RST in Windsor ONChevrolet Silverado 1500 LTZ in Windsor ONChevrolet Silverado 1500 LT Trail Boss in Windsor ONChevrolet Silverado 1500 LT1 in Windsor ONChevrolet Silverado 1500 Custom in Windsor ONChevrolet Silverado 1500 High Country in Windsor ONChevrolet Silverado 1500 Custom Trail Boss in Windsor ONChevrolet Silverado 1500 Work Truck in Windsor ON
Chevrolet Silverado 1500 in Detroit MIChevrolet Silverado 1500 in Lake Orion MIChevrolet Silverado 1500 in Ann Arbor MIChevrolet Silverado 1500 in Howell MIChevrolet Silverado 1500 in Toledo OHChevrolet Silverado 1500 in Flint MIChevrolet Silverado 1500 in Jackson MIChevrolet Silverado 1500 in Lansing MIChevrolet Silverado 1500 in Cleveland OH
Chevrolet Silverado 1500 in Windsor ONOld Chevy Trucks for Sale in Windsor ONClassic Muscle Cars for Sale in Windsor ONChevrolet Trucks For Sale in Windsor ONCheap Muscle Cars for Sale in Windsor ONWork Trucks for Sale in Windsor ONReliable Cars For Sale in Windsor ONAmerican Made Trucks For Sale in Windsor ONBest Pickup Trucks For Sale in Windsor ONBest Cars Under $5,000 For Sale in Windsor ON
All Used CarsManual Transmission CarsLuxury CarsCars with Red InteriorCheap Manual CarsHybrid CarsSports CarsElectric SUVsCheap TrucksSmall CarsThird Row SUVsThree Quarter Ton TrucksLifted TrucksManual Transmission TrucksDiesel TrucksHybrid SUVsDually TrucksOne Ton TrucksCheap SUVsLifted Ford Trucks4x4 TrucksWork TrucksAWD SUVsFord TrucksChevrolet TrucksToyota TrucksTrucks Under $10,000Cars Under $15,000Sports Cars Under $20,000Trucks Under $20,000Used Sedans for Sale with Low Mileage in WindsorUsed SUVs / Crossovers for Sale with Low Mileage in WindsorUsed Hatchbacks for Sale with Low Mileage in WindsorUsed Convertibles for Sale with Low Mileage in WindsorUsed Vans for Sale with Low Mileage in WindsorUsed Minivans for Sale with Low Mileage in WindsorUsed Pickup Trucks for Sale with Low Mileage in WindsorUsed Coupes for Sale with Low Mileage in WindsorUsed Wagons for Sale with Low Mileage in Windsor
