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New and used
2026 Chevrolet Silverado 2500 trucks
for sale
near
Woodbury, CT
49 matches
30 miles from 06798
Be the first to know!
Est.
$400
/mo*
- Down Payment
- $0
- Net trade-in value
- $0
- Months
- 72
- APR
- 7.0%
- Sales tax
- 0.0%
*Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.
**Your Saved Vehicles list will be shared along with your contact information when you submit a vehicle request to a dealership. To opt out of this sharing, please view your options on Cars.com Privacy Notice.
New
2026 Chevrolet Silverado 2500 Custom
$55,213
MSRP $58,555
$500 price drop
Ingersoll Auto of Pawling
Vehicle information
Ext. color: Summit White
Int. color: Jet Black
Drivetrain: Four-wheel Drive
Fuel type: Gasoline
Transmission: Automatic
Engine: 6.6L V-8 gasoline direct injection, variable valve control, regu
Stock #: N136174
VIN: 1GC5KME70TF136174
Features
Convenience:
Keyless Entry, Keyless Start, Navigation System, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Premium Sound System, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Blind Spot Monitor, Brake Assist, Lane Departure Warning, Rear Cross Traffic Alert, Stability Control
Reviews
Ingersoll Auto of Pawling review
Good vibes
Extremely nice staff, very professional team players from service desk to the shop. A very clean and safely run facility. Waiting area was comfortable. Service was done in a reasonable time. Service prices appear to be fair. Will definitely continue with my service here, also would consider a purchase from them in the future.
New
2026 Chevrolet Silverado 2500 WT
$53,100
MSRP $57,100
$500 price drop
Loehmann-Blasius Chevrolet
Vehicle information
Ext. color: Summit White
Int. color: Jet Black
Drivetrain: Four-wheel Drive
Fuel type: Gasoline
Transmission: Automatic
Engine: 6.6L V-8 gasoline direct injection, variable valve control, regu
Stock #: TR11620T26
VIN: 1GC4KLE77TF120091
Features
Convenience:
Keyless Entry, Keyless Start, Navigation System
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Premium Sound System, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Blind Spot Monitor, Brake Assist, Lane Departure Warning, Rear Cross Traffic Alert, Stability Control
Reviews
Loehmann-Blasius Chevrolet review
Great dealer.
Great dealer. No hassle. In my new vehicle the same day. Smooth transaction. Very happy with whole experience.
New
2026 Chevrolet Silverado 2500 LT
$75,609
MSRP $78,109
$500 price drop
Executive Chevrolet
Vehicle information
Ext. color: Summit White
Int. color: Jet Black, Cloth seat trim
Drivetrain: Four-wheel Drive
Fuel type: Gasoline
Transmission: Automatic
Engine: 6.6L V-8 gasoline direct injection, variable valve control, regu
Stock #: 26092
VIN: 1GC4KNEY6TF143138
Features
Convenience:
Heated Steering Wheel, Keyless Entry, Keyless Start, Navigation System
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Blind Spot Monitor, Brake Assist, Lane Departure Warning, Rear Cross Traffic Alert, Stability Control
Reviews
Executive Chevrolet review
Fantastic Experience
Had a great experience buying a used car here. Everyone I dealt with was friendly and knowledgeable. I never felt pressured, and being a single female, that was important to me. They gave me a fair price on my trade-in, and their cars are reasonably priced. Will Anderson was a terrific sales guy, and Jill and Matt guided me through all the paperwork. *Highly* recommend this dealership!
New
2026 Chevrolet Silverado 2500 LT
$63,850
MSRP $67,350
$500 price drop
Executive Chevrolet
Vehicle information
Ext. color: Gray
Int. color: Jet Black, Leather-appointed front outboard seat t
Drivetrain: Four-wheel Drive
Fuel type: Gasoline
Transmission: Automatic
Engine: 6.6L V-8 gasoline direct injection, variable valve control, regu
Stock #: 26065
VIN: 2GC4KNE78T1113279
Features
Convenience:
Heated Steering Wheel, Keyless Entry, Keyless Start, Navigation System
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Premium Sound System, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Blind Spot Monitor, Brake Assist, Lane Departure Warning, Rear Cross Traffic Alert, Stability Control
Seating:
Leather Seats
Reviews
Executive Chevrolet review
C8 Corvette repair
Although I live on Long Island, I chose to bring my 2021 Corvette back to Executive (where I purchased it) for a minor problem. I was impressed with the service mgr.(Kevin) because he was concerned that the Vette was parked under a tree, and told an employee to move it so it wouldn't get soiled(sap). I was grateful that Jennifer was able to get me an appointment in less than 24 hours of me calling her. Mark was my service advisor and he was a pleasure to deal with- he took the time to explain to me the problem and the steps they took, and the phone calls they made to Chevrolet, to resolve the problem. When the repair was completed the Corvette tech. (Steve) parked the car off to the side where it would be "safe". Everybody that handled the car treated it with respect. Although it's almost a 300 mile roundtrip from my home, I will definitely use Executive for my scheduled services.
New
2026 Chevrolet Silverado 2500 LT
$67,350
MSRP $67,350
Executive Chevrolet
Vehicle information
Ext. color: Lakeshore Blue Metallic
Int. color: Jet Black, Leather-appointed front outboard seat trim
Drivetrain: Four-wheel Drive
Fuel type: Gasoline
Transmission: Automatic
Engine: 6.6L V-8 gasoline direct injection, variable valve control, regu
Stock #: 26069
VIN: 2GC4KNE75T1114356
Features
Convenience:
Heated Steering Wheel, Keyless Entry, Keyless Start, Navigation System
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Blind Spot Monitor, Brake Assist, Lane Departure Warning, Rear Cross Traffic Alert, Stability Control
Seating:
Leather Seats
Reviews
Executive Chevrolet review
The dealer knew their product, fair and let you make your
The dealer knew their product, fair and let you make your own decision. The sales person was wonderful.
No photo available
New
2026 Chevrolet Silverado 2500 LT
$65,635
$500 price drop
Northwest Hills
Vehicle information
Ext. color: Summit White
Int. color: Jet Black
Drivetrain: Four-wheel Drive
Fuel type: Gasoline
Transmission: Automatic
Engine: 6.6L V-8 gasoline direct injection, variable valve control, regu
Stock #: C26-138
VIN: 2GC4KNE7XT1123392
Features
Convenience:
Heated Seats, Heated Steering Wheel, Keyless Entry, Keyless Start, Navigation System, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Premium Sound System, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Blind Spot Monitor, Brake Assist, LED Headlights, Lane Departure Warning, Rear Cross Traffic Alert, Stability Control
Reviews
Northwest Hills review
Great service every time
I bring my fleet vehicle here for repairs/maintenance. Other dealerships have treated me like a second class customer because the fleet company pays for everything. I have never once felt that way at Sullivan's. They are always kind and have gone above and beyond for me at times. My husband became a loyal customer here because of their great customer service.
No photo available
New
2026 Chevrolet Silverado 2500 Custom
$55,520
$500 price drop
Northwest Hills
Vehicle information
Ext. color: Sterling Gray Metallic
Int. color: Jet Black
Drivetrain: Four-wheel Drive
Fuel type: Diesel
Transmission: Automatic
Engine: Duramax 6.6L V-8 diesel direct injection, intercooled turbo, die
Stock #: C26-157
VIN: 1GC5KME76TF149866
Features
Convenience:
Keyless Entry, Keyless Start, Navigation System, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Premium Sound System, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Blind Spot Monitor, Brake Assist, Lane Departure Warning, Rear Cross Traffic Alert, Stability Control
Reviews
Northwest Hills review
Vinny at Sullivan's Northwest Hills was great to work
Vinny at Sullivan's Northwest Hills was great to work with and to buy a car from. It was truly a good experience. He was very knowledgeable and let you lead the conversation. I will buy my next vehicle from Vinny the next time I need one.
Vehicle information
Ext. color: Sterling Gray Metallic
Int. color: Jet Black
Drivetrain: Four-wheel Drive
Fuel type: Gasoline
Transmission: 10-Speed Automatic
Engine: 6.6L V-8 gasoline direct injection, variable valve control, regu
Stock #: C26064
VIN: 1GC5KNE77TF133777
Features
Convenience:
Heated Seats, Heated Steering Wheel, Keyless Entry, Keyless Start, Navigation System, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Premium Sound System, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Blind Spot Monitor, Brake Assist, Lane Departure Warning, Rear Cross Traffic Alert, Stability Control
Seating:
Leather Seats
Reviews
Hamden Chevrolet review
Great service, very professional, did take long in and
Great service, very professional, did take long in and out quick.price very reasonable, very nice people, everything was excellent and all problems that were found were explained
There are additional matching cars outside your search area.
Partial matches are generated by applying your search criteria to a larger search area. Our goal is to help you discover additional cars that match your search preferences.
As a benefit to some of our dealer customers, we display their listings first.
New
2026 Chevrolet Silverado 2500 LT
$63,680
$500 price drop
Arnold Chevrolet
Vehicle information
Ext. color: Exterior, Sharkskin Met-1 (130H)
Int. color: Sterling Gray Metallic
Drivetrain: Four-wheel Drive
Fuel type: Gasoline
Transmission: Automatic
Engine: 6.6L V-8 gasoline direct injection, variable valve control, regu
Stock #: 26-1114
VIN: 1GC4KNE7XTF105919
Features
Convenience:
Heated Steering Wheel, Keyless Entry, Keyless Start, Navigation System
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Blind Spot Monitor, Brake Assist, Lane Departure Warning, Rear Cross Traffic Alert, Stability Control
New
2026 Chevrolet Silverado 2500 Custom
$57,950
$500 price drop
DePaula Chevrolet
Vehicle information
Ext. color: Summit White
Int. color: Black
Drivetrain: Four-wheel Drive
Fuel type: Gasoline
Transmission: 10-Speed Automatic
Engine: 6.6L V8 16V GDI OHV
Stock #: T32919
VIN: 1GC4KME7XTF121550
Features
Convenience:
Keyless Entry, Keyless Start, Remote Start
Entertainment:
Apple CarPlay®, Bluetooth®, Premium Sound System, Satellite Radio, USB Port
Exterior:
Alloy Wheels, Tow Hitch
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Rear Cross Traffic Alert, Stability Control
New
2026 Chevrolet Silverado 2500 WT
$54,268
MSRP $57,845
$1,078 price drop
Imperial Chevrolet
Vehicle information
Ext. color: Summit White
Int. color: Jet Black
Drivetrain: Four-wheel Drive
Fuel type: Gasoline
Transmission: Automatic
Engine: 6.6L V-8 gasoline direct injection, variable valve control, regu
Stock #: 126060
VIN: 2GC4KLE73T1105028
Features
Convenience:
Keyless Entry, Keyless Start, Navigation System
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Premium Sound System, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Blind Spot Monitor, Brake Assist, Lane Departure Warning, Rear Cross Traffic Alert, Stability Control
New
2026 Chevrolet Silverado 2500 LT
$83,145
East Hills Chevrolet of Freeport
Vehicle information
Ext. color: Black
Int. color: Jet Black
Drivetrain: Four-wheel Drive
Fuel type: Diesel
Transmission: 10-Speed Automatic
Engine: 6.6L V8 32V DDI OHV Turbo Diesel
Stock #: F0225
VIN: 1GC4KNEYXTF129727
Features
Convenience:
Keyless Start
Entertainment:
Apple CarPlay®, Bluetooth®, Premium Sound System, Satellite Radio, USB Port
Exterior:
Alloy Wheels, Tow Hitch
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
New
2026 Chevrolet Silverado 2500 Custom
$71,125
MSRP $71,125
Bob Valenti Chevrolet
Vehicle information
Ext. color: Summit White
Int. color: Jet Black
Drivetrain: Four-wheel Drive
Fuel type: Diesel
Transmission: Automatic
Engine: Duramax 6.6L V-8 diesel direct injection, intercooled turbo, die
Stock #: 4068
VIN: 1GC4KMEY3TF121981
Features
Convenience:
Keyless Entry, Keyless Start, Navigation System, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Blind Spot Monitor, Brake Assist, Lane Departure Warning, Rear Cross Traffic Alert, Stability Control
New
2026 Chevrolet Silverado 2500 LT
$65,380
MSRP $67,880
$1,000 price drop
Central Chevrolet
Vehicle information
Ext. color: Sterling Gray Metallic
Int. color: Jet Black, Cloth Seat Trim
Drivetrain: Four-wheel Drive
Fuel type: Gasoline
Transmission: Automatic
Engine: 6.6L V-8 gasoline direct injection, variable valve control, regu
Stock #: FMRWFVO
VIN: 2GC4KNE72T1122690
Features
Convenience:
Keyless Entry, Keyless Start, Navigation System
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
New
2026 Chevrolet Silverado 2500 Custom
$56,905
$1,000 price drop
Paul Masse Chevrolet
Vehicle information
Ext. color: Summit White
Int. color: Jet Black
Drivetrain: Four-wheel Drive
Fuel type: Gasoline
Transmission: 10-Speed Automatic
Engine: 6.6L V8 16V GDI OHV
Stock #: CK6091
VIN: 1GC5KME77TF144398
Features
Convenience:
Keyless Start
Entertainment:
Apple CarPlay®, Bluetooth®, Premium Sound System, Satellite Radio, USB Port
Exterior:
Alloy Wheels, Tow Hitch
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
New
2026 Chevrolet Silverado 2500 LT
$69,940
MSRP $69,940
$2,000 price drop
East Hartford Chevrolet
Vehicle information
Ext. color: Gxd
Int. color: Jet Black
Drivetrain: Four-wheel Drive
Fuel type: Gasoline
Transmission: Automatic
Engine: 6.6L V-8 gasoline direct injection, variable valve control, regu
Stock #: 260129
VIN: 2GC4KNE70T1106147
Features
Convenience:
Heated Seats, Heated Steering Wheel, Keyless Entry, Keyless Start, Navigation System, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Premium Sound System, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Blind Spot Monitor, Brake Assist, LED Headlights, Lane Departure Warning, Rear Cross Traffic Alert, Stability Control
Seating:
Leather Seats
New
2026 Chevrolet Silverado 2500 Custom
$69,995
Ruge's Automotive Inc.
Vehicle information
Ext. color: Summit White
Int. color: Jet Black
Drivetrain: Four-wheel Drive
Fuel type: Diesel
Transmission: 10-Speed Automatic
Engine: 6.6L V8 32V DDI OHV Turbo Diesel
Stock #: 26M043
VIN: 2GC4KMEY3T1105173
Features
Convenience:
Keyless Start
Entertainment:
Apple CarPlay®, Bluetooth®, Premium Sound System, Satellite Radio, USB Port
Exterior:
Alloy Wheels, Tow Hitch
Safety:
Automatic Emergency Braking, Backup Camera, Brake Assist, Lane Departure Warning, Stability Control
New
2026 Chevrolet Silverado 2500 Custom
$57,485
$500 price drop
Bomnin Chevrolet Buick GMC Nanuet
Vehicle information
Ext. color: Sterling
Int. color: Jet Blk Clth
Drivetrain: Four-wheel Drive
Fuel type: Diesel
Transmission: Automatic
Engine: Duramax 6.6L V-8 diesel direct injection, intercooled turbo, die
Stock #: T1123366
VIN: 2GC4KME76T1123366
Features
Convenience:
Keyless Entry, Keyless Start, Navigation System, Remote Start
Entertainment:
Android Auto®, Apple CarPlay®, Bluetooth®, Premium Sound System, USB Port, WiFi Hotspot
Exterior:
Alloy Wheels, Tow Hitch, Tow Hooks
Safety:
Automatic Emergency Braking, Backup Camera, Blind Spot Monitor, Brake Assist, Lane Departure Warning, Rear Cross Traffic Alert, Stability Control
*Estimated payments are calculated by Cars.com and are for informational purposes only. We’ve estimated your taxes based on your provided ZIP code. These estimates do not include title, registration fees, lien fees, or any other fees that may be imposed by a governmental agency in connection with the sale and financing of the vehicle. Other taxes may apply. They do not represent a financing offer or a guarantee of credit from the seller. Actual terms vary by lender.
**Your Saved Vehicles list will be shared along with your contact information when you submit a vehicle request to a dealership. To opt out of this sharing, please view your options on Cars.com Privacy Notice.
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