Used Pickup Trucks for Sale nearMiddletown, CT
3,803 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Bright White Clearcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 36,416
- Stock #:
- CU629390A
- VIN:
- 1C6SRFFT8MN570010
Sponsored by Middletown Chevrolet
2021 RAM 1500
Big Horn Crew Cab 4WD
36,416 mi
Middletown, CT
1 mi away
Fair Deal
$34,589
- Year:
- 2017
- Make:
- Toyota
- Model:
- Tundra
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 381 hp 5.7L V8
- Exterior color:
- Super White
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 6-Speed Automatic
- Mileage:
- 172,948
- Stock #:
- A53440A
- VIN:
- 5TFUY5F15HX620045
New arrival
Sponsored Listing
2017 Toyota Tundra
SR5 Double Cab 5.7L 4WD
172,948 mi
Milford, CT
32 mi away
Great Deal
$17,890
- 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
Sponsored Listing
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
89,178 mi
Thomaston, CT
23 mi away
Good Deal
$29,981
- Year:
- 2014
- Make:
- Toyota
- Model:
- Tacoma
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 236 hp 4L V6
- Exterior color:
- Magnetic Gray Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- Automatic
- Mileage:
- 145,375
- Stock #:
- 30406B
- VIN:
- 3TMLU4EN1EM138759
New arrival
2014 Toyota Tacoma
Double Cab SB V6 4WD
145,375 mi
New London, CT
31 mi away
Fair Deal
$19,649
- 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:
- Summit White
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 80,395
- Stock #:
- 25-363A
- VIN:
- 1GCHTDEN4J1265859
Price drop
-$3,740
2018 Chevrolet Colorado
Z71 Extended Cab LB 4WD
80,395 mi
Torrington, CT
29 mi away
Good Deal
$23,726
$19,986
- Year:
- 2020
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Sting-Gray Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 48,928
- Stock #:
- 146167U
- VIN:
- 1C6HJTFG7LL146167
Price drop
-$2,541
2020 Jeep Gladiator
Overland Crew Cab 4WD
48,928 mi
New Milford, CT
40 mi away
Fair Deal
$31,391
$28,850
- Year:
- 2022
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 395 hp 5.7L V8
- Exterior color:
- Delmonico Red Pearlcoat
- Fuel type:
- Gasoline
- Interior color:
- Diesel Gray/Black
- Mileage:
- 49,024
- Stock #:
- 5546A
- VIN:
- 1C6SRFFT4NN374597
Price drop
-$1,100
2022 RAM 1500
Big Horn Crew Cab 4WD
49,024 mi
West Springfield, MA
38 mi away
Great Deal
$34,195
$33,095
- Year:
- 2018
- Make:
- Ford
- Model:
- F-150
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 375 hp 3.5L V6
- Exterior color:
- Shadow Black
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 36,085
- Stock #:
- U15026A
- VIN:
- 1FTFW1EG5JFE06682
2018 Ford F-150
Lariat SuperCrew LB 4WD
36,085 mi
Watertown, CT
23 mi away
Good Deal
$33,779
- Year:
- 2018
- 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 (Graphite Metallic)
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 59,287
- Stock #:
- 1827267
- VIN:
- 1GCVKREC5JZ227267
New arrival
2018 Chevrolet Silverado 1500
LT Double Cab 4WD
59,287 mi
Naugatuck, CT
21 mi away
Good Deal
$25,793
- Year:
- 2023
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 305 hp 3.6L V6
- Exterior color:
- Diamond Black Crystal Pearl Coat
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Transmission:
- 8-Speed Automatic
- Mileage:
- 20,916
- Stock #:
- UR1345
- VIN:
- 1C6RRFFG7PN549283
2023 RAM 1500
Big Horn Crew Cab 4WD
20,916 mi
Riverhead, NY
43 mi away
Good Deal
$35,052
- 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:
- Blue Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 22,084
- Stock #:
- JU3437T
- VIN:
- 1GCUDDEDXNZ586878
2022 Chevrolet Silverado 1500
LT Crew Cab 4WD
22,084 mi
Port Jefferson Station, NY
48 mi away
Good Deal
$36,105
- Year:
- 2014
- Make:
- GMC
- Model:
- Sierra 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 5.3L V8 Flex Fuel Vehicle
- Exterior color:
- Gray
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Flex Fuel Vehicle
- Transmission:
- Automatic
- Mileage:
- 90,242
- VIN:
- 1GTV2UECXEZ338227
New arrival
2014 GMC Sierra 1500
SLE Double Cab 4WD
90,242 mi
Southwick, MA
36 mi away
Great Deal
$15,290
- 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:
- Silver Sky Metallic
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Cement
- Transmission:
- Automatic
- Mileage:
- 41,910
- Stock #:
- 46480UU
- VIN:
- 5TFCZ5AN4MX263163
2021 Toyota Tacoma
TRD Sport Double Cab 4WD
41,910 mi
Riverhead, NY
43 mi away
Great Deal
$34,170
Popular Pickup Truck reviews
4.5 Overall rating(10221 reviews)
Jun 6, 2026
2012 Chevrolet LT Crew Cab 4WD
Before purchasing a used Silverado 2500HD, I would strongly recommend checking the overall condition of the truck with special attention to rust, the transmission, suspension, and maintenance history. Look closely at the rocker panels, cab corners, wheel wells, frame rails, brake lines, and fuel lines for excessive rust, flaking metal, or holes. During the test drive, make sure the transmission shifts smoothly without slipping, shuddering, hard shifts, or delayed engagement into drive or reverse, and ask whether it is the original transmission or if it has ever been rebuilt or replaced. Check the engine for oil leaks, coolant leaks, unusual noises, excessive exhaust smoke, or warning lights, and ask if major components such as the water pump, radiator, or thermostat have been replaced. Pay close attention to the steering and suspension by listening for clunks, checking for loose steering, and looking for uneven tire wear that could indicate worn ball joints, tie rods, wheel bearings, or other front-end components. Also inspect the brakes for pulsation, soft pedal feel, or rusted lines, and examine the tires for uneven wear, dry rot, or signs that an alignment or suspension issue may be present. Most importantly, ask for maintenance records and receipts for major repairs, as a well-documented truck is generally a much safer purchase than one with an unknown service history. For a high-mileage Silverado 2500HD, rust, transmission condition, front-end wear, four-wheel-drive operation, and cooling system maintenance are the areas most likely to lead to expensive repairs if they have been neglected.
Apr 23, 2026
2020 Ford XLT Crew Cab 4WD
Great condition really nice interior, really good priced drives and runs great
Jan 23, 2026
2022 Hyundai SEL Premium Crew Cab AWD
The car comes with incredible features I wasn’t even prepared for. Everything is thoughtfully crafted and they make use of every inch of space with hidden storage compartments. I love it so far
Dec 6, 2025
2019 Ford XLT SuperCrew RWD
Great vehicle! Has everything I need in a strong durable truck! Will definitely buy Ford again.
Oct 17, 2025
2022 GMC Denali Ultimate Crew Cab 4WD
Love this truck! Love the inline 6 diesel! And my fiance loves the massaging seats!
- Year:
- 2019
- Make:
- RAM
- Model:
- 2500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 410 hp 6.4L V8
- Exterior color:
- Billet Silver Metallic
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 90,766
- Stock #:
- JU3551T
- VIN:
- 3C6UR5CJXKG675627
New arrival
2019 RAM 2500
Tradesman Crew Cab 4WD
90,766 mi
Port Jefferson Station, NY
48 mi away
Good Deal
$26,602
- Year:
- 2023
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 305 hp 3.6L V6
- Exterior color:
- GY
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Transmission:
- 8-Speed Automatic
- Mileage:
- 15,322
- Stock #:
- UR1521
- VIN:
- 1C6RRFFG9PN666475
2023 RAM 1500
Big Horn Crew Cab 4WD
15,322 mi
Riverhead, NY
43 mi away
Great Deal
$34,052
- 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:
- 153,098
- Stock #:
- F2558197M
- VIN:
- 1GCRYCEF6KZ295103
Price drop
-$599
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
153,098 mi
Watertown, CT
23 mi away
Good Deal
$18,298
$17,699
- Year:
- 2013
- Make:
- GMC
- Model:
- Sierra 3500HD
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 360 hp 6L V8
- Exterior color:
- White
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 91,144
- Stock #:
- 112
- VIN:
- 1GT422CG6DF234470
2013 GMC Sierra 3500HD
Work Truck Crew Cab 4WD
91,144 mi
Thomaston, CT
23 mi away
Good Deal
$20,698
- Year:
- 2019
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 395 hp 5.7L V8
- Exterior color:
- Delmonico Red Pearl Coat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Diesel Gray/Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 71,908
- Stock #:
- UR1919
- VIN:
- 1C6RR7LT9KS558228
2019 RAM 1500
Classic Big Horn Crew Cab 4WD
71,908 mi
Riverhead, NY
43 mi away
Good Deal
$24,973
- Year:
- 2024
- Make:
- GMC
- Model:
- Sierra 3500HD
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 401 hp 6.6L V8
- Exterior color:
- Titanium Rush Metallic
- Fuel type:
- Gasoline
- Interior color:
- Jet Black With Kalahari Accents
- Transmission:
- Automatic
- Mileage:
- 32,436
- Stock #:
- G26084A
- VIN:
- 1GT49VE7XRF190720
2024 GMC Sierra 3500HD
AT4 Crew Cab 4WD
32,436 mi
New Britain, CT
10 mi away
Great Deal
$57,429
- Year:
- 2019
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 4.3L V6 Flex Fuel Vehicle
- Exterior color:
- Shadow Gray Metallic
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 48,574
- VIN:
- 1GCRYAEH4KZ413820
2019 Chevrolet Silverado 1500
LT Double Cab 4WD
48,574 mi
Yantic, CT
28 mi away
Good Deal
$26,590
- Year:
- 2025
- Make:
- Ford
- Model:
- F-150 Lightning
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- Electric
- Exterior color:
- Carbonized Gray Metallic
- Fuel type:
- Electric
- Interior color:
- Medium Dark Slate
- Transmission:
- 1-Speed Automatic
- Mileage:
- 12,025
- Stock #:
- U28525
- VIN:
- 1FTVW3LK4SWG10292
2025 Ford F-150 Lightning
XLT SuperCrew AWD
12,025 mi
Litchfield, CT
32 mi away
Great Deal
$45,589
- 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:
- Gray (Granite Crystal Metallic Clearcoat)
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Diesel Gray/Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 50,138
- Stock #:
- U2102
- VIN:
- 1C6RR7FT1HS619608
New arrival
2017 RAM 1500
Express Quad Cab 4WD
50,138 mi
Milford, CT
31 mi away
Fair Deal
$23,552
- Year:
- 2012
- Make:
- Honda
- Model:
- Ridgeline
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 250 hp 3.5L V6
- Exterior color:
- Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 5-Speed Automatic
- Mileage:
- 134,063
- VIN:
- 5FPYK1F75CB455186
Price drop
-$800
Sponsored Listing
2012 Honda Ridgeline
Sport
134,063 mi
Waterbury, CT
20 mi away
Good Deal
$12,499
$11,699
4.5 Overall rating for Pickup Truck
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Filter by rating
Britt O
Reviewed a 2012 Chevrolet LT Crew Cab 4WD on Jun 6, 2026
Before purchasing a used Silverado 2500HD, I would strongly recommend checking the overall condition of the truck with special attention to rust, the transmission, suspension, and maintenance history. Look closely at the rocker panels, cab corners, wheel wells, frame rails, brake lines, and fuel lines for excessive rust, flaking metal, or holes. During the test drive, make sure the transmission shifts smoothly without slipping, shuddering, hard shifts, or delayed engagement into drive or reverse, and ask whether it is the original transmission or if it has ever been rebuilt or replaced. Check the engine for oil leaks, coolant leaks, unusual noises, excessive exhaust smoke, or warning lights, and ask if major components such as the water pump, radiator, or thermostat have been replaced. Pay close attention to the steering and suspension by listening for clunks, checking for loose steering, and looking for uneven tire wear that could indicate worn ball joints, tie rods, wheel bearings, or other front-end components. Also inspect the brakes for pulsation, soft pedal feel, or rusted lines, and examine the tires for uneven wear, dry rot, or signs that an alignment or suspension issue may be present. Most importantly, ask for maintenance records and receipts for major repairs, as a well-documented truck is generally a much safer purchase than one with an unknown service history. For a high-mileage Silverado 2500HD, rust, transmission condition, front-end wear, four-wheel-drive operation, and cooling system maintenance are the areas most likely to lead to expensive repairs if they have been neglected.
Is this review helpful?
Josiah L
Reviewed a 2020 Ford XLT Crew Cab 4WD on Apr 23, 2026
Great condition really nice interior, really good priced drives and runs great
Is this review helpful?
Jesse S
Reviewed a 2022 Hyundai SEL Premium Crew Cab AWD on Jan 23, 2026
The car comes with incredible features I wasn’t even prepared for. Everything is thoughtfully crafted and they make use of every inch of space with hidden storage compartments. I love it so far
Is this review helpful?
Dale W
Reviewed a 2019 Ford XLT SuperCrew RWD on Dec 6, 2025
Great vehicle! Has everything I need in a strong durable truck! Will definitely buy Ford again.
Is this review helpful?
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