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

4X4 trucks for Sale in Chestertown, MD

1,736 results
Chestertown, MD
2022 Chevrolet Silverado 1500 RST Crew Cab 4WD Pointe GMC

2022 Chevrolet Silverado 1500

RST Crew Cab 4WD

61,421 miles

$36,934

Fair Deal
Certified Pre-Owned
Penns Grove, NJ
48 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:
Summit White
Fuel type:
Gasoline
Mileage:
61,421
Stock number:
G3522B
VIN:
1GCUYEED9NZ186482

Sponsored

2020 Ford F-150 XLT SuperCrew LB 4WD

2020 Ford F-150

XLT SuperCrew LB 4WD

105,552 miles

$26,200

Fair Deal
Denton, MD
27 mi away
Year:
2020
Make:
Ford
Model:
F-150
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
375 hp 3.5L V6
Exterior color:
Oxford White
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
105,552
Stock number:
F250267A
VIN:
1FTFW1E46LFC30220

Sponsored

2022 Toyota Tacoma SR5 V6 Double Cab LB 4WD

2022 Toyota Tacoma

SR5 V6 Double Cab LB 4WD

33,124 miles

$34,995

Fair Deal
Elkton, MD
30 mi away
Year:
2022
Make:
Toyota
Model:
Tacoma
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
278 hp 3.5L V6
Exterior color:
Magnetic Gray Metallic
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Interior color:
Cement
Transmission:
6-Speed Automatic
Mileage:
33,124
Stock number:
R709
VIN:
3TMDZ5BN1NM139264

Sponsored

2019 Chevrolet Silverado 2500HD LTZ Crew Cab 4WD

2019 Chevrolet Silverado 2500HD

LTZ Crew Cab 4WD

50,234 miles

$50,991

Fair Deal
Laurel, MD
43 mi away
Year:
2019
Make:
Chevrolet
Model:
Silverado 2500HD
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
6.6L V8 Biodiesel
Exterior color:
Gray (Graphite Metallic)
Fuel type:
Biodiesel
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
50,234
Stock number:
KF168038
VIN:
1GC1KTEY9KF168038

2022 Ford F-450 Super Duty King Ranch Crew Cab LB DRW 4WD

2022 Ford F-450 Super Duty

King Ranch Crew Cab LB DRW 4WD

36,759 miles

$79,921

Good Deal
Milford, DE
39 mi away
Year:
2022
Make:
Ford
Model:
F-450 Super Duty
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
6.7L V8 Biodiesel
Exterior color:
Oxford White
Fuel type:
Biodiesel
Interior color:
Java
Transmission:
Automatic
Mileage:
36,759
Stock number:
1261380A
VIN:
1FT8W4DT1NEF77031

2018 Chevrolet Silverado 1500 LTZ Crew Cab 4WD

2018 Chevrolet Silverado 1500

LTZ Crew Cab 4WD

139,145 miles

$23,875

Great Deal
Milford, DE
39 mi away
Year:
2018
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Centennial Blue Metallic
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic Overdrive
Mileage:
139,145
Stock number:
7257211B
VIN:
3GCUKSEJ8JG448038

Preparing for a close up...

Photos coming soon

2018 RAM 3500 Chassis

Tradesman Crew Cab 4WD

30,386 miles

$27,959

Great Deal
Quarryville, PA
48 mi away
Year:
2018
Make:
RAM
Model:
3500 Chassis
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
370 hp 6.4L V8
Exterior color:
Bright White Clearcoat - PW7
Fuel type:
Gasoline
Interior color:
Diesel Gray/Black - X8
Transmission:
Automatic
Mileage:
30,386
Stock number:
C23211A
VIN:
3C7WRTCJ6JG201522

Preparing for a close up...

Photos coming soon

2018 Chevrolet Colorado

Z71 Extended Cab LB 4WD

37,260 miles

$23,282

Great Deal
Quarryville, PA
48 mi away
Year:
2018
Make:
Chevrolet
Model:
Colorado
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
308 hp 3.6L V6
Exterior color:
Deepwood Green Metallic - GMW
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Interior color:
Jet Black - HH1
Transmission:
Automatic
Mileage:
37,260
Stock number:
C21916B
VIN:
1GCHTDENXJ1251349

Preparing for a close up...

Photos coming soon

2016 Ford F-150

XLT SuperCrew 4WD

105,430 miles

$21,581

Good Deal
Dover, DE
29 mi away
Year:
2016
Make:
Ford
Model:
F-150
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
5L V8 Flex Fuel Vehicle
Exterior color:
Shadow Black
Combined gas mileage:
18 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
Automatic
Mileage:
105,430
Stock number:
26063A
VIN:
1FTEW1EF2GFD14540

Preparing for a close up...

Photos coming soon

2022 RAM 2500

Tradesman Crew Cab LB 4WD

64,902 miles

$29,999

Good Deal
Penns Grove, NJ
48 mi away
Year:
2022
Make:
RAM
Model:
2500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
410 hp 6.4L V8
Exterior color:
Bright White Clearcoat
Fuel type:
Gasoline
Mileage:
64,902
Stock number:
2836
VIN:
3C6UR5HJ9NG130953

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

High Country Crew Cab 4WD

72,171 miles

$41,000

Great Deal
Seaford, DE
49 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:
Radiant Red Tintcoat
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
72,171
Stock number:
26009A
VIN:
1GCUDJED2PZ207115

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 2500HD

Custom Crew Cab 4WD

70,739 miles

$38,800

Great Deal
Easton, MD
32 mi away
Year:
2024
Make:
Chevrolet
Model:
Silverado 2500HD
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
401 hp 6.6L V8
Exterior color:
Black
Fuel type:
Gasoline
Interior color:
Jet Black, Cloth seat trim
Transmission:
Automatic
Mileage:
70,739
Stock number:
EC26230A
VIN:
2GC4YME77R1144234

Preparing for a close up...

Photos coming soon

2018 Ford F-150

XLT SuperCab 4WD

93,361 miles

$20,995

Great Deal
Dover, DE
29 mi away
Year:
2018
Make:
Ford
Model:
F-150
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
White Gold
Interior color:
Medium Light Camel
Transmission:
Automatic
Mileage:
93,361
Stock number:
DVX0282A
VIN:
1FTEX1EP6JFB19182

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

RST Crew Cab 4WD

51,667 miles

$33,800

Good Deal
Parkville, MD
28 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)
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
51,667
Stock number:
LU120051
VIN:
3GCUYEED6MG120051

Preparing for a close up...

Photos coming soon

2019 RAM 2500

Limited Crew Cab 4WD

72,077 miles

$48,999

Great Deal
Penns Grove, NJ
48 mi away
Year:
2019
Make:
RAM
Model:
2500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
370 hp 6.7L I6 Diesel
Exterior color:
Diamond Black Crystal Pearlcoat
Fuel type:
Diesel
Transmission:
6-Speed Automatic
Mileage:
72,077
Stock number:
2806
VIN:
3C6UR5SL4KG553493

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 2500HD

LTZ Crew Cab 4WD

87,315 miles

$44,877

Good Deal
Milford, DE
38 mi away
Year:
2019
Make:
Chevrolet
Model:
Silverado 2500HD
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
6.6L V8 Biodiesel
Exterior color:
Black
Fuel type:
Biodiesel
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
87,315
Stock number:
250215A
VIN:
1GC1KTEY3KF166611

Preparing for a close up...

Photos coming soon

2020 RAM 3500

Big Horn Crew Cab 4WD

55,319 miles

$46,926

Good Deal
Milford, DE
39 mi away
Year:
2020
Make:
RAM
Model:
3500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
370 hp 6.7L I6 Diesel
Exterior color:
Gray (Maximum Steel Metallic Clearcoat)
Fuel type:
Diesel
Interior color:
Diesel Gray/Black
Transmission:
6-Speed Automatic
Mileage:
55,319
Stock number:
1261324A
VIN:
3C63R3DL1LG295545

Preparing for a close up...

Photos coming soon

2017 RAM 1500

Laramie Crew Cab 4WD

89,116 miles

$23,900

Good Deal
Wilmington, DE
45 mi away
Year:
2017
Make:
RAM
Model:
1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
395 hp 5.7L V8
Exterior color:
Bright White Clearcoat
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Canyon Brown/Light Frost Beige
Transmission:
8-Speed Automatic
Mileage:
89,116
Stock number:
HS800537
VIN:
1C6RR7VT9HS800537

Preparing for a close up...

Photos coming soon

2021 RAM 1500

Laramie Crew Cab 4WD

78,535 miles

$30,929

Good Deal
Penns Grove, NJ
48 mi away
Year:
2021
Make:
RAM
Model:
1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
395 hp 5.7L V8
Exterior color:
Hydro Blue Pearlcoat
Fuel type:
Gasoline
Mileage:
78,535
Stock number:
G3648A
VIN:
1C6SRFJT9MN621599

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

59,945 miles

$32,997

Great Deal
Dover, DE
29 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:
Cherry Red Tintcoat
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black, Cloth seat trim
Transmission:
Automatic
Mileage:
59,945
Stock number:
26142A
VIN:
1GCPYCEF8MZ420032

Preparing for a close up...

Photos coming soon

2021 Toyota Tacoma

TRD Pro Double Cab 4WD

56,745 miles

$39,299

Great Deal
Milford, DE
38 mi away
Year:
2021
Make:
Toyota
Model:
Tacoma
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
278 hp 3.5L V6
Exterior color:
Super White
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
56,745
Stock number:
P129021
VIN:
5TFCZ5AN5MX260210

Preparing for a close up...

Photos coming soon

2019 Chevrolet Colorado

LT Crew Cab 4WD

51,738 miles

$24,200

Good Deal
Towson, MD
32 mi away
Year:
2019
Make:
Chevrolet
Model:
Colorado
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
308 hp 3.6L V6
Exterior color:
Black
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
51,738
Stock number:
NB236376
VIN:
1GCGTCEN5K1236376

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

LTZ Crew Cab 4WD

65,798 miles

$33,995

Good Deal
Dover, DE
29 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:
19 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
65,798
Stock number:
DU00409A
VIN:
1GCUYGED8KZ142657

Preparing for a close up...

Photos coming soon

2025 Toyota Tacoma

TRD Off-Road Double Cab 4WD

16,582 miles

$43,000

Good Deal
Bowie, MD
40 mi away
Year:
2025
Make:
Toyota
Model:
Tacoma
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Exterior color:
Celestial Silver
Interior color:
Boulder/Black
Transmission:
8-Speed Automatic
Mileage:
16,582
Stock number:
560109A
VIN:
3TYLC5LN9ST025122

Sponsored

  • AWD cars for Sale in Chestertown MD

  • Ford Trucks for Sale in Chestertown MD

  • Chevrolet Trucks For Sale in Chestertown MD

  • Dodge Trucks For Sale in Chestertown MD

  • Best Cars In Snow For Sale in Chestertown MD

  • Fuel Efficient Cars for Sale in Chestertown MD

  • Hybrid Cars For Sale in Chestertown MD

  • Cars with Online Financing For Sale in Chestertown MD

  • Third Row SUVs For Sale in Chestertown MD

  • American Made Trucks For Sale in Chestertown MD

  • Affordable Luxury Cars For Sale in Chestertown MD

  • Cars with Free Test Drive at Home For Sale in Chestertown MD

  • 4X4 trucks for Sale in Baltimore MD

  • 4X4 trucks for Sale in Dover DE

  • 4X4 trucks for Sale in Newark DE

  • 4X4 trucks for Sale in Washington DC

  • 4X4 trucks for Sale in Lancaster PA

  • 4X4 trucks for Sale in Hanover PA

  • 4X4 trucks for Sale in Salisbury MD

  • 4X4 trucks for Sale in Philadelphia PA

  • 4X4 trucks for Sale in Reading PA

  • 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

  • Hampstead Preowned Auto Sales

  • DARCARS Lexus of Silver Spring

  • Koons Clarksville Chevrolet GMC

  • Hyundai of Dundalk

  • National Motors - Ellicott City

  • Koons Ford of Baltimore

  • Auto Team Delaware

  • Koons White Marsh Chevrolet

  • Mercedes-Benz of Catonsville

  • Union Park Automotive Group

  • JBA Chevrolet

  • DARCARS Toyota of Silver Spring

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

© 2025 CarGurus, Inc., All Rights Reserved.