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 Poestenkill, NY

125 results
Poestenkill, NY
2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD Country Nissan

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

24,760 miles

$39,998

Fair Deal
Hadley, MA
55 mi away
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:
Northsky Blue Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
24,760
Stock number:
NA1792
VIN:
3GCPDCED8NG679874

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

39,376 miles

$37,999

Fair Deal
Warrensburg, NY
57 mi away
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:
Sand Dune Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
39,376
Stock number:
6546PRB
VIN:
3GCPDCED1NG534448

Sponsored

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

24,251 miles

$36,000

Fair Deal
Pawling, NY
80 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:
Northsky Blue Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
24,251
Stock number:
A605415
VIN:
3GCPDCEK4NG605415

Sponsored

2020 Chevrolet Silverado 1500 Custom Trail Boss Double Cab 4WD

2020 Chevrolet Silverado 1500

Custom Trail Boss Double Cab 4WD

14,901 miles

$31,891

Great Deal
Brattleboro, VT
53 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:
Silver Ice Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
14,901
Stock number:
C26040A
VIN:
1GCRYCEF3LZ293973

2021 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

44,505 miles

$33,999

Good Deal
Warrensburg, NY
57 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
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
44,505
Stock number:
6848PRA
VIN:
1GCPYCEF6MZ171584

2022 Chevrolet Silverado 1500 Custom Trail Boss Crew Cab 4WD

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

65,410 miles

$31,099

Good Deal
Bristol, CT
76 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:
65,410
Stock number:
UA38236A
VIN:
3GCPDCEK4NG569791

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

25,071 miles

$43,858

Good Deal
Leominster, MA
92 mi away
Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Slate Gray Metallic
Fuel type:
Diesel
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
25,071
Stock number:
HL6363A
VIN:
3GCUKCE8XSG245723

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

45,484 miles

$31,997

Great Deal
Hudson, NY
30 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:
White
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
45,484
Stock number:
2173P
VIN:
1GCPYCEF3LZ260351

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

113,737 miles

$24,995

Good Deal
Windsor Locks, CT
72 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:
Jet Black
Transmission:
Automatic
Mileage:
113,737
Stock number:
275538
VIN:
3GCPYCEF6LG275538

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

95,600 miles

$25,999

Good Deal
Rhinebeck, NY
53 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:
95,600
Stock number:
M4743
VIN:
3GCPYCEF2KG152981

Preparing for a close up...

Photos coming soon

2022 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

39,376 miles

$37,999

Fair Deal
Warrensburg, NY
57 mi away
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:
Sand Dune Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
39,376
Stock number:
6546PRB
VIN:
3GCPDCED1NG534448

Preparing for a close up...

Photos coming soon

2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

6,300 miles

$45,097

Good Deal
Store transfer to Albany, NY
217 mi away • Price includes $99 shipping Price includes $99 shipping
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:
Brown (Tan)
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
6,300
Stock number:
28249598
VIN:
3GCPKCEK1TG122953

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

70,757 miles

$25,999

Great Deal
Middletown, CT
91 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
Interior color:
Jet Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
70,757
Stock number:
BM4183
VIN:
1GCPYCEF7KZ275417

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

119,644 miles

$23,995

Good Deal
Manchester, CT
82 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:
Jet Black
Transmission:
Automatic
Mileage:
119,644
Stock number:
224999
VIN:
3GCPYCEF7LG224999

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

25,071 miles

$43,858

Good Deal
Leominster, MA
92 mi away
Year:
2025
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Slate Gray Metallic
Fuel type:
Diesel
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
25,071
Stock number:
HL6363A
VIN:
3GCUKCE8XSG245723

Sponsored

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

  • Chevrolet Silverado 1500 LT in Poestenkill NY

  • Chevrolet Silverado 1500 RST in Poestenkill NY

  • Chevrolet Silverado 1500 LTZ in Poestenkill NY

  • Chevrolet Silverado 1500 LT Trail Boss in Poestenkill NY

  • Chevrolet Silverado 1500 LT1 in Poestenkill NY

  • Chevrolet Silverado 1500 Custom in Poestenkill NY

  • Chevrolet Silverado 1500 High Country in Poestenkill NY

  • Chevrolet Silverado 1500 Custom Trail Boss in Poestenkill NY

  • Chevrolet Silverado 1500 Work Truck in Poestenkill NY

  • Chevrolet Silverado 1500 in Albany NY

  • Chevrolet Silverado 1500 in Pittsfield MA

  • Chevrolet Silverado 1500 in Brattleboro VT

  • Chevrolet Silverado 1500 in Chicopee MA

  • Chevrolet Silverado 1500 in Hartford CT

  • Chevrolet Silverado 1500 in Newburgh NY

  • Chevrolet Silverado 1500 in Utica NY

  • Chevrolet Silverado 1500 in Worcester MA

  • Chevrolet Silverado 1500 in New Haven CT

  • Chevrolet Silverado 1500 in Poestenkill NY

  • Old Chevy Trucks for Sale in Poestenkill NY

  • Classic Muscle Cars for Sale in Poestenkill NY

  • Chevrolet Trucks For Sale in Poestenkill NY

  • Cheap Muscle Cars for Sale in Poestenkill NY

  • Work Trucks for Sale in Poestenkill NY

  • Reliable Cars For Sale in Poestenkill NY

  • American Made Trucks For Sale in Poestenkill NY

  • Best Pickup Trucks For Sale in Poestenkill NY

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

  • 2019 Chevrolet Silverado 1500 Custom Trail Boss in Poestenkill 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 in Poestenkill

  • Used SUVs / Crossovers for Sale with Low Mileage in Poestenkill

  • Used Hatchbacks for Sale with Low Mileage in Poestenkill

  • Used Convertibles for Sale with Low Mileage in Poestenkill

  • Used Vans for Sale with Low Mileage in Poestenkill

  • Used Minivans for Sale with Low Mileage in Poestenkill

  • Used Pickup Trucks for Sale with Low Mileage in Poestenkill

  • Used Coupes for Sale with Low Mileage in Poestenkill

  • Used Wagons for Sale with Low Mileage in Poestenkill

  • Mohawk Chevrolet

  • Bedard Bros Auto Sales

  • McGee Chevrolet of Greenwich

  • Fina Auto Mall

  • Langway Chevrolet Volkswagen of Manchester

  • Cobleskill Chevrolet GMC

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.