Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearOakville, CT
160 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- 71,786
- Stock #:
- M5080
- VIN:
- 3GCUDCED8PG122758
New arrival
Sponsored by Ruge's Automotive
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
71,786 mi
Rhinebeck, NY
49 mi away
Good Deal
$34,944
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 92,992
- Stock #:
- CU4125B
- VIN:
- 1GCPYCEF0KZ223191
Price drop
-$1,424
Sponsored Listing
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
92,992 mi
Beacon, NY
46 mi away
Good Deal
$25,700
$24,276
- 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:
- 8-Speed Automatic
- Mileage:
- 13,807
- Stock #:
- M5066
- VIN:
- 3GCPKCEK0SG108461
Sponsored Listing
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
13,807 mi
Rhinebeck, NY
49 mi away
Fair Deal
$43,075
- 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:
- 10,418
- Stock #:
- U20778T
- VIN:
- 3GCPKCEK4SG326516
Price drop
-$2,388
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
10,418 mi
Home delivery from St James, NY
Free home delivery
Great Deal
$41,168
$38,780
- Year:
- 2026
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 11,602
- Stock #:
- S1560A
- VIN:
- 3GCUKCED1TG144617
Price drop
-$1,364
2026 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
11,602 mi
Stafford Springs, CT
46 mi away
Fair Deal
$47,724
$46,360
- 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
-$1,000
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,903 mi
Home delivery from Gorham, NH
Price includes $420 shipping
Great Deal
$33,309
$32,309
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 92,992
- Stock #:
- CU4125B
- VIN:
- 1GCPYCEF0KZ223191
Price drop
-$1,424
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
92,992 mi
Beacon, NY
46 mi away
Good Deal
$25,700
$24,276
- 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:
- 112,673
- Stock #:
- 330377
- VIN:
- 1GCPYCEF1KZ330377
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
112,673 mi
Suffield, CT
35 mi away
Good Deal
$22,339
- 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
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black, Cloth seat trim
- Transmission:
- 8-Speed Automatic
- Mileage:
- 34,003
- Stock #:
- PV26086A
- VIN:
- 3GCPDCEKXRG398597
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
34,003 mi
Chicopee, MA
47 mi away
Fair Deal
$39,566
- 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:
- Summit White
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 89,178
- Stock #:
- C9068209A
- VIN:
- 3GCPYCEF1MG344184
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
89,178 mi
Thomaston, CT
4 mi away
Good Deal
$28,283
- 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 (Satin Steel Metallic)
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gideon/Very Dark Atmosphere
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 60,733
- Stock #:
- ZR64242A
- VIN:
- 1GCPYCEF7LZ123588
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
60,733 mi
East Hartford, CT
25 mi away
Good Deal
$30,398
- 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:
- Brown (Tan)
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 59,400
- Stock #:
- GB0805
- VIN:
- 3GCPDCEK1NG667404
Photos coming soon
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
59,400 mi
Carmel, NY
33 mi away
Fair Deal
$32,670
- 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:
- Shadow Gray Metallic
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 41,657
- Stock #:
- 20325
- VIN:
- 1GCPYCEF4MZ289181
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
41,657 mi
Home delivery from Mesa, AZ
Price includes $2,176 shipping
Fair Deal
$35,171
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Summit White
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 60,943
- Stock #:
- 29517
- VIN:
- 1GCPYCEKXNZ109832
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
60,943 mi
Home delivery from Cambridge, OH
Price includes $686 shipping
Fair Deal
$30,662
- 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:
- 21,405
- Stock #:
- BU2554A
- VIN:
- 3GCUDCED7PG364215
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
21,405 mi
Poughkeepsie, NY
43 mi away
Fair Deal
$41,675
- 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:
- 93,992
- Stock #:
- 144813B
- VIN:
- 1GCPYCEK5NZ144813
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
93,992 mi
Home delivery from Dallas, TX
Price includes $1,435 shipping
Fair Deal
$28,160
- 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
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 43,725
- Stock #:
- Z4575
- VIN:
- 3GCPDCEK0RG141805
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
43,725 mi
Brookfield, CT
19 mi away
Good Deal
$35,992
- 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:
- Gray
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 80,543
- Stock #:
- 184095
- VIN:
- 1GCRYCEF4KZ184095
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
80,543 mi
Home delivery from Peabody, MA
Price includes $252 shipping
Fair Deal
$27,752
- 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:
- Blue
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 53,625
- Stock #:
- 70139418
- VIN:
- 3GCPDCEK0PG123320
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
53,625 mi
Store transfer to Waterbury, CT
Price includes $1,599 shipping
Fair Deal
$36,597
- 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 (Satin Steel Metallic)
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 103,145
- Stock #:
- U1683MA
- VIN:
- 1GCPYCEL8NZ172209
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
103,145 mi
Cheshire, CT
10 mi away
Fair Deal
$29,564
- 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
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 32,641
- Stock #:
- MX5558
- VIN:
- 1GCPYCEF3MZ296638
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
32,641 mi
Home delivery from Louisville, TN
Price includes $1,282 shipping
Fair Deal
$36,637
- 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:
- Gideon/Very Dark Atmosphere
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 61,843
- Stock #:
- 3U1795
- VIN:
- 1GCPYCEF3MZ358300
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
61,843 mi
Home delivery from Lenoir, NC
Price includes $628 shipping
Fair Deal
$34,117
- 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:
- 68,630
- Stock #:
- 110992
- VIN:
- 3GCPDCEK0NG534178
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
68,630 mi
Home delivery from Nashua, NH
Price includes $345 shipping
Good Deal
$29,740
- 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:
- 112,673
- Stock #:
- 330377
- VIN:
- 1GCPYCEF1KZ330377
Sponsored Listing
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
112,673 mi
Suffield, CT
35 mi away
Good Deal
$22,339
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in Oakville, CT?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $25,981.00. The average price has decreased by -5.2% since last year. The 160 for sale near Oakville, CT on CarGurus, range from $19,028 to $63,523 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in Oakville, CT have no reported accidents or damage?
145 out of 160 for sale near Oakville, CT 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.
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