CarGurus Logo Homepage Link
  • Buy
    • Used cars
    • New cars
    • Certified pre-owned
    • Start your purchase online
    • Dealerships near me
  • Sell
    • Sell my car
    • Car values
    • Sell my car FAQs
  • Finance
    • Prequalify for financing
    • How does it work?
    • Financing FAQs
  • Research
    • Test drive reviews
    • Price trends
    • Tips & advice
    • Electric cars
    • Compare cars
  • Discover
    The latest way to shop:
    smarter research, better
    listings.
  • Saved cars & searches
  • Sign in / Register
    • My account
    • Saved searches
    • Saved cars
    • Recommended cars
    • Browsing history
    • Financing dashboard
      • United States (EN)
      • Estados Unidos (ES)
      • Canada (EN)
      • Canada (FR)
      • United Kingdom

Used Chevrolet Silverado 1500 Custom Trail Boss for Sale near Callicoon, NY

204 results
Callicoon, NY
2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Ruge's Automotive

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

10,208 miles

$37,900

Fair Deal
Rhinebeck, NY
62 mi away
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:
Silver Ice Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
10,208
Stock number:
M4775
VIN:
3GCPDCEK1NG611799

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

120,650 miles

$21,500

Good Deal
Bangor, PA
61 mi away
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:
White
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
6-Speed Automatic Overdrive
Mileage:
120,650
Stock number:
KZ376230
VIN:
1GCRYCEF2KZ376230

Sponsored

2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

37,988 miles

$36,490

Good Deal
Certified Pre-Owned
Nanuet, NY
73 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:
Red Hot
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
37,988
Stock number:
C123540A
VIN:
3GCPDCEK3PG123540

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

62,500 miles

$27,992

Fair Deal
Johnstown, NY
92 mi away
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
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
62,500
Stock number:
N16323A
VIN:
1GCRYCEF2KZ335922

2023 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

35,344 miles

$38,996

Good Deal
Certified Pre-Owned
Chittenango, NY
97 mi away
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:
Black
Transmission:
Automatic
Mileage:
35,344
Stock number:
PPG180550
VIN:
3GCUDCEDXPG180550

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

71,773 miles

$30,000

Great Deal
Albany, NY
92 mi away
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:
Gray (Satin Steel Metallic)
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
71,773
Stock number:
43146
VIN:
1GCPYCEF5MZ260840

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

83,639 miles

$27,880

Fair Deal
Litchfield, CT
95 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
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
83,639
Stock number:
U28091
VIN:
1GCRYCEF7LZ259731

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

24,381 miles

$36,465

Fair Deal
Norwich, NY
56 mi away
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:
Black
Transmission:
8-Speed Automatic
Mileage:
24,381
Stock number:
0514UT
VIN:
3GCPDCEK7NG608843

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

42,082 miles

$32,000

Great Deal
Albany, NY
92 mi away
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
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
42,082
Stock number:
42956
VIN:
1GCPYCEF5MZ376961

Preparing for a close up...

Photos coming soon

2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

2,783 miles

$45,900

Good Deal
Latham, NY
95 mi away
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
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
2,783
Stock number:
SS25958A
VIN:
3GCPKCEK5TG172495

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

40,702 miles

$34,500

Good Deal
Albany, NY
92 mi away
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:
Gray (Satin Steel Metallic)
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
40,702
Stock number:
43466
VIN:
1GCPYCEF2MZ298753

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

30,190 miles

$33,200

Great Deal
Wilkes Barre, PA
54 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Black
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
30,190
Stock number:
T50693B
VIN:
1GCPYCEK7NZ101039

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

21,141 miles

$39,599

Good Deal
Lake Katrine, NY
58 mi away
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
Transmission:
Automatic
Mileage:
21,141
Stock number:
26373A
VIN:
3GCUDCED2PG301796

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

47,616 miles

$34,999

Good Deal
Elmira, NY
97 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:
Brown (Tan)
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
47,616
Stock number:
D25-71A
VIN:
3GCPDCEK9PG130170

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

66,598 miles

$31,899

Good Deal
Lake Katrine, NY
58 mi away
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:
White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
66,598
Stock number:
TR25530
VIN:
1GCPYCEL8MZ280179

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

115,000 miles

$24,995

Good Deal
Apalachin, NY
58 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:
Automatic
Mileage:
115,000
Stock number:
23924
VIN:
3GCPYCEF9LG201742

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / New York
  6. / Callicoon
  • Chevrolet Silverado 1500 LT in Callicoon NY

  • Chevrolet Silverado 1500 RST in Callicoon NY

  • Chevrolet Silverado 1500 LTZ in Callicoon NY

  • Chevrolet Silverado 1500 LT Trail Boss in Callicoon NY

  • Chevrolet Silverado 1500 LT1 in Callicoon NY

  • Chevrolet Silverado 1500 Custom in Callicoon NY

  • Chevrolet Silverado 1500 High Country in Callicoon NY

  • Chevrolet Silverado 1500 Custom Trail Boss in Callicoon NY

  • Chevrolet Silverado 1500 Work Truck in Callicoon NY

  • Chevrolet Silverado 1500 in Binghamton NY

  • Chevrolet Silverado 1500 in Wilkes Barre PA

  • Chevrolet Silverado 1500 in Newburgh NY

  • Chevrolet Silverado 1500 in Allentown PA

  • Chevrolet Silverado 1500 in Ithaca NY

  • Chevrolet Silverado 1500 in New York NY

  • Chevrolet Silverado 1500 in Albany NY

  • Chevrolet Silverado 1500 in Utica NY

  • Chevrolet Silverado 1500 in Stamford CT

  • Chevrolet Silverado 1500 in Callicoon NY

  • Old Chevy Trucks for Sale in Callicoon NY

  • Classic Muscle Cars for Sale in Callicoon NY

  • Chevrolet Trucks For Sale in Callicoon NY

  • Cheap Muscle Cars for Sale in Callicoon NY

  • Work Trucks for Sale in Callicoon NY

  • Reliable Cars For Sale in Callicoon NY

  • American Made Trucks For Sale in Callicoon NY

  • Best Pickup Trucks For Sale in Callicoon NY

  • Best Cars Under $5,000 For Sale in Callicoon NY

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Callicoon NY

  • All Used Cars

  • Manual Transmission Cars

  • Luxury Cars

  • Cars with Red Interior

  • Cheap Manual Cars

  • Hybrid Cars

  • Sports Cars

  • Electric SUVs

  • Cheap Trucks

  • Small Cars

  • Third Row SUVs

  • Three Quarter Ton Trucks

  • Lifted Trucks

  • Manual Transmission Trucks

  • Diesel Trucks

  • Hybrid SUVs

  • Dually Trucks

  • One Ton Trucks

  • Cheap SUVs

  • Lifted Ford Trucks

  • 4x4 Trucks

  • Work Trucks

  • AWD SUVs

  • Ford Trucks

  • Chevrolet Trucks

  • Toyota Trucks

  • Trucks Under $10,000

  • Cars Under $15,000

  • Sports Cars Under $20,000

  • Trucks Under $20,000

  • Used Sedans for Sale with Low Mileage

  • Used SUVs / Crossovers for Sale with Low Mileage

  • Used Hatchbacks for Sale with Low Mileage

  • Used Convertibles for Sale with Low Mileage

  • Used Vans for Sale with Low Mileage

  • Used Minivans for Sale with Low Mileage

  • Used Pickup Trucks for Sale with Low Mileage

  • Used Coupes for Sale with Low Mileage

  • Used Wagons for Sale with Low Mileage

  • Ray Price Auto Park Mt. Pocono

  • Hornbeck Chevrolet

Connect with us
Download our app
Download on the App Store Get it on Google Play
  • Company
  • About CarGurus
  • Our team
  • Press
  • Investor relations
  • Price trends
  • Careers
  • Advertise with CarGurus
  • For dealers
  • Dealer signup
  • Dealer resources
  • Terms
  • Terms of use
  • Privacy policy
  • Interest-based ads
  • Security
  • Help
  • Help center
  • Contact us
Click for the BBB Business Review of this Auto Listing Service in Cambridge MA
    • United States (EN)
    • Estados Unidos (ES)
    • Canada (EN)
    • Canada (FR)
    • United Kingdom

© 2026 CarGurus, Inc., All Rights Reserved.