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 Waterville, NY

176 results
Sangerfield, NY
2020 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Auto Outlet of Wolcott

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

69,870 miles

$33,495

Fair Deal
Wolcott, NY
75 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:
Cajun Red Tintcoat
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
69,870
Stock number:
A9580
VIN:
1GCPYCEF3LZ153624

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

115,265 miles

$21,778

Good Deal
Lake Katrine, NY
97 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:
Black
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
115,265
Stock number:
26287A
VIN:
1GCRYCEF8KZ194421

Sponsored

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

68,185 miles

$30,483

Great Deal
Certified Pre-Owned
Utica, NY
18 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:
Red Hot
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
68,185
Stock number:
F39783A
VIN:
1GCPYCEF9MZ326757

Sponsored

2019 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

63,335 miles

$27,995

Good Deal
Boonville, NY
35 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:
Silver Ice Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
63,335
Stock number:
1437RA
VIN:
1GCRYCEF5KZ266109

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

42,082 miles

$31,800

Great Deal
Albany, NY
81 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

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

33,527 miles

$34,880

Good Deal
Liverpool, NY
48 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:
Gray
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
33,527
Stock number:
S27673
VIN:
1GCPYCEK0NZ144167

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

71,773 miles

$30,000

Great Deal
Albany, NY
81 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

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

54,623 miles

$33,995

Good Deal
Auburn, NY
59 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:
Blue
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
54,623
Stock number:
13495A
VIN:
1GCPYCEF0MZ186288

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

115,265 miles

$21,778

Good Deal
Lake Katrine, NY
97 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:
Black
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
115,265
Stock number:
26287A
VIN:
1GCRYCEF8KZ194421

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

81,439 miles

$26,998

Great Deal
Lake Katrine, NY
97 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:
Red
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
81,439
Stock number:
26228A
VIN:
1GCPYCEF8MZ154091

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

73,086 miles

$30,999

Good Deal
Hudson, NY
95 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:
Shadow Gray Metallic
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
73,086
Stock number:
2200P
VIN:
1GCPYCEF7MZ408339

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

34,107 miles

$39,995

Fair Deal
Certified Pre-Owned
Ballston Spa, NY
77 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:
34,107
Stock number:
90226B
VIN:
3GCUDCEDXPG332214

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

81,601 miles

$27,988

Good Deal
Herkimer, NY
22 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:
Black
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
81,601
Stock number:
8237A
VIN:
3GCPYCEF6KG267163

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

50,705 miles

$32,550

Fair Deal
East Syracuse, NY
36 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:
Silver Ice Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
50,705
Stock number:
CSS260358A
VIN:
1GCPYCEF5KZ388444

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

68,185 miles

$30,483

Great Deal
Certified Pre-Owned
Utica, NY
18 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:
Red Hot
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
68,185
Stock number:
F39783A
VIN:
1GCPYCEF9MZ326757

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

66,598 miles

$30,999

Great Deal
Lake Katrine, NY
97 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

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

33,527 miles

$34,880

Good Deal
Liverpool, NY
48 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:
Gray
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
33,527
Stock number:
S27673
VIN:
1GCPYCEK0NZ144167

Sponsored

  1. Home
  2. / Used Cars
  3. / Chevrolet Silverado 1500
  4. / Custom Trail Boss
  5. / New York
  6. / Waterville

  • Chevrolet Silverado 1500 LT in Waterville NY

  • Chevrolet Silverado 1500 RST in Waterville NY

  • Chevrolet Silverado 1500 LTZ in Waterville NY

  • Chevrolet Silverado 1500 LT Trail Boss in Waterville NY

  • Chevrolet Silverado 1500 LT1 in Waterville NY

  • Chevrolet Silverado 1500 Custom in Waterville NY

  • Chevrolet Silverado 1500 High Country in Waterville NY

  • Chevrolet Silverado 1500 Custom Trail Boss in Waterville NY

  • Chevrolet Silverado 1500 Work Truck in Waterville NY

  • Chevrolet Silverado 1500 in Utica NY

  • Chevrolet Silverado 1500 in Syracuse NY

  • Chevrolet Silverado 1500 in Binghamton NY

  • Chevrolet Silverado 1500 in Ithaca NY

  • Chevrolet Silverado 1500 in Albany NY

  • Chevrolet Silverado 1500 in Elmira NY

  • Chevrolet Silverado 1500 in Pittsfield MA

  • Chevrolet Silverado 1500 in Rochester NY

  • Chevrolet Silverado 1500 in Wilkes Barre PA

  • Chevrolet Silverado 1500 in Waterville NY

  • Old Chevy Trucks for Sale in Waterville NY

  • Classic Muscle Cars for Sale in Waterville NY

  • Chevrolet Trucks For Sale in Waterville NY

  • Cheap Muscle Cars for Sale in Waterville NY

  • Work Trucks for Sale in Waterville NY

  • Reliable Cars For Sale in Waterville NY

  • American Made Trucks For Sale in Waterville NY

  • Best Pickup Trucks For Sale in Waterville NY

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

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Waterville 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

  • NYE Automotive Group

  • Sharon Chevrolet, Inc.

  • LeadCar Chevrolet Yorkville

  • Sun 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.