Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearBridgehampton, NY
162 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Summit White
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 28,769
- Stock #:
- XPA2047
- VIN:
- 1GCPYCEL7NZ128900
Sponsored by Napoli Auto Xpress
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
28,769 mi
Milford, CT
45 mi away
Fair Deal
$38,991
- 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:
- Slate Gray Metallic
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 34,003
- Stock #:
- PV26086A
- VIN:
- 3GCPDCEKXRG398597
Sponsored Listing
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
34,003 mi
Chicopee, MA
86 mi away
Fair Deal
$43,087
- 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:
- Summit White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 2,808
- Stock #:
- B8311
- VIN:
- 3GCPKCEK6SG112367
Sponsored Listing
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
2,808 mi
Raynham, MA
95 mi away
Fair Deal
$45,522
- Year:
- 2025
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Black
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 4,286
- Stock #:
- PM213863
- VIN:
- 3GCUKCE89SG213863
New arrival
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
4,286 mi
Home delivery from Honesdale, PA
Price includes $160 shipping
Great Deal
$44,545
- 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:
- 153,929
- Stock #:
- F2558197M
- VIN:
- 1GCRYCEF6KZ295103
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
153,929 mi
Watertown, CT
60 mi away
Fair Deal
$20,287
- 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:
- Shadow Gray Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 56,969
- Stock #:
- 3927
- VIN:
- 1GCRYCEF9KZ249670
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
56,969 mi
Home delivery from Belford, NJ
Price includes $250 shipping
Good Deal
$29,923
- 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:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 43,590
- Stock #:
- P42470A
- VIN:
- 3GCUDCED8PG130990
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
43,590 mi
Warwick, RI
72 mi away
Good Deal
$38,877
- 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:
- Black
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 25,595
- Stock #:
- GB0401
- VIN:
- 3GCPDCEK8PG340310
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
25,595 mi
Carmel, NY
78 mi away
Good Deal
$37,766
- 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:
- Black
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 51,065
- Stock #:
- 22696A
- VIN:
- 3GCPDCEK3PG106074
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,065 mi
Home delivery from Tampa, FL
Price includes $1,112 shipping
Great Deal
$36,091
- 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:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 113,737
- Stock #:
- 275538
- VIN:
- 3GCPYCEF6LG275538
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
113,737 mi
Windsor Locks, CT
69 mi away
Good Deal
$24,794
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 82,729
- Stock #:
- K5824A
- VIN:
- 1GCRYCEF8LZ286243
2020 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
82,729 mi
Johnston, RI
74 mi away
Fair Deal
$29,398
- 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:
- Shadow Gray Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 122,864
- Stock #:
- 175496
- VIN:
- 3GCPYCEF9LG175496
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
122,864 mi
Home delivery from Dawsonville, GA
Price includes $984 shipping
Fair Deal
$27,228
- 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:
- Blue
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 10-Speed Automatic
- Mileage:
- 102,783
- Stock #:
- 5211
- VIN:
- 3GCPYCEF9MG436837
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
102,783 mi
Old Saybrook, CT
26 mi away
Fair Deal
$28,543
- 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:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 51,903
- Stock #:
- 610597T
- VIN:
- 3GCPDCED4NG610597
Price drop
-$900
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,903 mi
Home delivery from Gorham, NH
Price includes $478 shipping
Good Deal
$37,167
$36,267
- 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:
- Glacier Blue Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- JET BLACK
- Transmission:
- Automatic
- Mileage:
- 89,467
- Stock #:
- P581637B
- VIN:
- 3GCPDCED8NG581637
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
89,467 mi
Home delivery from Livingston, TX
Price includes $2,158 shipping
Good Deal
$32,388
- 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:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 125,117
- Stock #:
- CU378338
- VIN:
- 1GCPYCEF0KZ378338
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
125,117 mi
Middletown, CT
45 mi away
Fair Deal
$24,492
- 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:
- Summit White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 53,768
- Stock #:
- PM174391
- VIN:
- 1GCPYCEL0NZ174391
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
53,768 mi
Home delivery from Pleasantville, NJ
Price includes $326 shipping
Good Deal
$35,561
- 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:
- Gray
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 57,412
- Stock #:
- CT12064
- VIN:
- 1GCRYCEF4KZ223400
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
57,412 mi
Manchester, CT
59 mi away
Good Deal
$28,494
- 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 $808 shipping
Great Deal
$32,718
- 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:
- Glacier Blue Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 82,773
- Stock #:
- 54173
- VIN:
- 3GCPDCEK6NG533147
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
82,773 mi
Home delivery from Cambridge, OH
Price includes $368 shipping
Fair Deal
$31,645
- 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:
- JET BLACK
- Transmission:
- 8-Speed Automatic
- Mileage:
- 63,090
- Stock #:
- SI1924A
- VIN:
- 1GCPYCEK6NZ109889
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
63,090 mi
Brooklyn, CT
63 mi away
Fair Deal
$34,787
- 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:
- 43,490
- Stock #:
- 313824
- VIN:
- 1GCRYCEF2KZ313824
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
43,490 mi
Huntington Sta, NY
57 mi away
Fair Deal
$33,065
- 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:
- Gray
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 62,775
- Stock #:
- 5019
- VIN:
- 1GCPYCEF0LZ168095
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
62,775 mi
Home delivery from Burton, MI
Price includes $600 shipping
Great Deal
$29,600
- 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:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 43,590
- Stock #:
- P42470A
- VIN:
- 3GCUDCED8PG130990
Sponsored Listing
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
43,590 mi
Warwick, RI
72 mi away
Good Deal
$38,877
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Bridgehampton, NY?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $27,081.34. The average price has decreased by -0.5% since last year. The 117 for sale near Bridgehampton, NY on CarGurus, range from $23,659 to $64,883 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Bridgehampton, NY have no reported accidents or damage?
117 out of 117 for sale near Bridgehampton, NY 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.
Relevant articles
Craig Fitzgerald
The Best Trucks Under $25,000 in 2026
New trucks cost more than ever, but the prices of used ones finally seem to be cooling. You still can't find the latest and fanciest full-sizes for budget prices, but fortunately, there are plenty of good trucks under $25,000 these days. Here, we've assembled a list of the best.
Craig Fitzgerald
The Best Cars to Tow Behind an RV in 2026
Not many new models can be towed behind an RV. We’ve identified several that are recommended for flat-towing according to their owner’s manual, and a few used models that have fewer technological or engineering restrictions.
CarGurus Editorial Team
Car Deals with 0% APR in July 2026
Our experts have tracked down the latest 0% APR car deals, as well as examined the pros and cons of interest-free car loans versus other financing options.
Chevrolet Silverado 1500 LT in Bridgehampton NYChevrolet Silverado 1500 RST in Bridgehampton NYChevrolet Silverado 1500 LTZ in Bridgehampton NYChevrolet Silverado 1500 LT Trail Boss in Bridgehampton NYChevrolet Silverado 1500 LT1 in Bridgehampton NYChevrolet Silverado 1500 Custom in Bridgehampton NYChevrolet Silverado 1500 High Country in Bridgehampton NYChevrolet Silverado 1500 Custom Trail Boss in Bridgehampton NYChevrolet Silverado 1500 Work Truck in Bridgehampton NY
Chevrolet Silverado 1500 in Holtsville NYChevrolet Silverado 1500 in New Haven CTChevrolet Silverado 1500 in Hartford CTChevrolet Silverado 1500 in Stamford CTChevrolet Silverado 1500 in Providence RIChevrolet Silverado 1500 in New Bedford MAChevrolet Silverado 1500 in Chicopee MAChevrolet Silverado 1500 in New York NYChevrolet Silverado 1500 in Worcester MA
Chevrolet Silverado 1500 in Bridgehampton NYOld Chevy Trucks for Sale in Bridgehampton NYClassic Muscle Cars for Sale in Bridgehampton NYChevrolet Trucks For Sale in Bridgehampton NYCheap Muscle Cars for Sale in Bridgehampton NYWork Trucks for Sale in Bridgehampton NYReliable Cars For Sale in Bridgehampton NYAmerican Made Trucks For Sale in Bridgehampton NYBest Pickup Trucks For Sale in Bridgehampton NYBest Cars Under $5,000 For Sale in Bridgehampton NY
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 BridgehamptonUsed SUVs / Crossovers for Sale with Low Mileage in BridgehamptonUsed Hatchbacks for Sale with Low Mileage in BridgehamptonUsed Convertibles for Sale with Low Mileage in BridgehamptonUsed Vans for Sale with Low Mileage in BridgehamptonUsed Minivans for Sale with Low Mileage in BridgehamptonUsed Pickup Trucks for Sale with Low Mileage in BridgehamptonUsed Coupes for Sale with Low Mileage in BridgehamptonUsed Wagons for Sale with Low Mileage in Bridgehampton
