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1,638 listings
- Price Drop$19,998fair price$1,383 below market
- 73,748 miles
- No accidents, 1 owner, personal use only
- 5 Seats
- Hertrich's Ford of Milford (160 mi away)
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Located in Milford, DE / 160 miles away from Chesapeake, VA
Serviced here, Non-Smoker vehicle, Originally bought here, Auto Check One Owner! Heated Leather Seats, Sunroof, Navigation, Back-Up Camera, Power Lift...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: Yes
Features and Specs:
Listing Information:
VIN: 1C4PJMDN6LD553399
Stock: P8527A
Certified Pre-Owned: No
Listed since: 06-01-2025 - New Listing$18,900fair price$976 below market
- 63,188 miles
- No accidents, 2 owners, personal use only
- 5 Seats
- Deacon Jones Chrysler Dodge Jeep Ram (144 mi away)
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Located in Smithfield, NC / 144 miles away from Chesapeake, VA
Recent Arrival! Certified. Sting-Gray Clearcoat 2020 Jeep Cherokee Latitude Plus 3.2L V6 FWD Comfort/Convenience Group (115V Auxiliary Power Outlet, A...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
Listing Information:
VIN: 1C4PJLLX6LD648901
Stock: J450167B
Certified Pre-Owned: Yes
Listed since: 07-09-2025 - $10,210fair price$444 below market
- 144,070 miles
- No accidents, 2 owners, personal use only
- 5 Seats, 21 City / 30 Hwy MPG
- Xride Cars (148 mi away)
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Located in Raleigh, NC / 148 miles away from Chesapeake, VA
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
25 Combined MPG (21 City/30 Highway)
Listing Information:
VIN: 1C4PJLDB6JD531478
Stock: 531478
Certified Pre-Owned: No - $23,998good price
- 23,613 miles
- No accidents, 1 owner, personal use
- 5 Seats
- CarMax (In-stock online)
- Transfer available from TX to VA*
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Located in Fort Worth, TX / 1,217 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: Yes
Features and Specs:
Listing Information:
VIN: 1C4PJMMN9ND529598
Stock: 27520522
Certified Pre-Owned: No - New Listing$24,998good price
- 23,945 miles
- No accidents, 1 owner, personal use
- 5 Seats
- CarMax (In-stock online)
- Transfer available from TX to VA*
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Located in Fort Worth, TX / 1,232 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
Listing Information:
VIN: 1C4PJMMNXND514303
Stock: 27599981
Certified Pre-Owned: No - New Listing$22,998fair price$129 above market
- 23,206 miles
- No accidents, 1 owner, personal use only
- 5 Seats, 20 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from FL to VA*
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Located in Fort Myers, FL / 774 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/29 Highway)
Listing Information:
VIN: 1C4PJLMX4ND515880
Stock: 27607858
Certified Pre-Owned: No - $26,119good price
- 22,955 miles
- No accidents, 1 owner, corporate fleet vehicle
- 5 Seats, 19 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Rockwall, TX / 1,174 miles away from Chesapeake, VA
Rare Find,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,Lane Keeping Assist,...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 1C4PJMDXXND501522
Stock: ND501522P
Certified Pre-Owned: No - $20,998fair price$401 below market
- 36,976 miles
- No accidents, 2 owners, personal use only
- 5 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from WA to VA*
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Located in Renton, WA / 2,432 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: Yes
Features and Specs:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 1C4PJMLB9LD625798
Stock: 27454857
Certified Pre-Owned: No - $25,498fair price$460 below market
- 26,262 miles
- No accidents, 1 owner, personal use
- 5 Seats
- Driveway (In-stock online)
- Home delivery*
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Located in Coon Rapids, MN / 1,062 miles away from Chesapeake, VA
CarFax No Accidents Reported,CarFax 1-Owner,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
Listing Information:
VIN: 1C4PJMMN8ND510413
Stock: PND510413
Certified Pre-Owned: Yes - New Listing$22,400fair price$495 below market
- 50,813 miles
- No accidents, 1 owner, personal use only
- 5 Seats, 19 City / 27 Hwy MPG
- Casey Toyota (51 mi away)
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Located in Williamsburg, VA / 51 miles away from Chesapeake, VA
ADULT DRIVEN!, Clean Carfax, Extended Warranty Available, GPS / NAVIGATION, Bluetooth, Apple CarPlay, 1 Owner, LEATHER, Local Trade, Manager's Special...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 1C4PJMDX3LD525772
Stock: TS50561
Certified Pre-Owned: No
Listed since: 07-03-2025 - $12,982great price$2,124 below market
- 83,583 miles
- 1 accident, 3 owners, corporate fleet vehicle
- 5 Seats, 22 City / 31 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Grants Pass, OR / 2,506 miles away from Chesapeake, VA
Rare Find,Back-Up Camera,Bluetooth,Brake Assist,4 Cylinder Engine,4-Wheel Disc Brakes,9-Speed A/T,A/C,A/T,ABS,Adjustable Steering Wheel,Aluminum Wheel...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
25 Combined MPG (22 City/31 Highway)
Listing Information:
VIN: 1C4PJLCB8LD515920
Stock: LD515920G
Certified Pre-Owned: No - New Listing$24,554fair price$250 below market
- 25,962 miles
- No accidents, 1 owner, corporate fleet vehicle
- 5 Seats, 18 City / 24 Hwy MPG
- Westgate Dodge Ram (139 mi away)
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Located in Wake Forest, NC / 139 miles away from Chesapeake, VA
2022 Jeep Cherokee Trail hawk This isnt your average soft-road crossover. The Trailhawk laughs in the face of gravel, snow, and that one road your GPS...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 1C4PJMBX7ND528048
Stock: 62902P
Certified Pre-Owned: No
Listed since: 06-06-2025 - New Listing$27,590good price$1,504 below market
- 29,336 miles
- 1 accident, 1 owner, personal use
- 5 Seats, 18 City / 24 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Chicago, IL / 746 miles away from Chesapeake, VA
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 1C4PJMBX2ND523310
Stock: 2003894751
Certified Pre-Owned: No
Listed since: 07-16-2025 - $18,990fair price$567 below market
- 68,336 miles
- No accidents, 4 owners, corporate fleet vehicle
- 5 Seats, 19 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Salem, OR / 2,474 miles away from Chesapeake, VA
CarFax No Accidents Reported,Rare Find,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyle...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
22 Combined MPG (19 City/27 Highway)
Listing Information:
VIN: 1C4PJMDX5LD563746
Stock: N563746
Certified Pre-Owned: No - $23,998fair price$913 below market
- 49,732 miles
- No accidents, 1 owner, personal use only
- 5 Seats, 18 City / 24 Hwy MPG
- CarMax (In-stock online)
- Transfer available from KS to VA*
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Located in Merriam, KS / 1,017 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: Yes
Features and Specs:
21 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 1C4PJMBX3ND555487
Stock: 27256200
Certified Pre-Owned: No - New Listing$26,590fair price
- 30,140 miles
- No accidents, 1 owner, personal use
- 5 Seats, 18 City / 24 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Dallas, TX / 1,195 miles away from Chesapeake, VA
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 1C4PJMBX6ND521852
Stock: 2003901161
Certified Pre-Owned: No
Listed since: 07-17-2025 - New Listing$18,999fair price$683 below market
- 73,744 miles
- No accidents, 1 owner, personal use only
- 5 Seats
- HoneyCar Charlottesville (151 mi away)
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Located in Charlottesville, VA / 151 miles away from Chesapeake, VA
HoneyCar provides The Sweetest Way to Buy or Sell Your Car. We take the Sour out of car buying with super low prices and a highly responsive team answ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
Listing Information:
VIN: 1C4PJMDN7LD549832
Stock: LD549832
Certified Pre-Owned: No
Listed since: 06-30-2025 - New Listing$22,998good price$1,861 below market
- 57,457 miles
- No accidents, 1 owner, personal use only
- 5 Seats, 18 City / 24 Hwy MPG
- CarMax (In-stock online)
- Transfer available from GA to VA*
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Located in Stockbridge, GA / 505 miles away from Chesapeake, VA
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: Yes
Features and Specs:
21 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 1C4PJMBXXND541652
Stock: 27496924
Certified Pre-Owned: No - New Listing$14,983fair price$1,057 below market
- 92,928 miles
- No accidents, 4 owners, rental vehicle
- 5 Seats, 22 City / 31 Hwy MPG
- Victory Nissan of Mechanicsville (86 mi away)
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Located in Mechanicsville, VA / 86 miles away from Chesapeake, VA
Recent Arrival! 2020 Jeep Cherokee Limited 2.4L I4 9-Speed 948TE Automatic FWDThis stunning vehicle has just arrived at Victory Nissan Mechanicsville ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
25 Combined MPG (22 City/31 Highway)
Listing Information:
VIN: 1C4PJLDB7LD565013
Stock: 83E06005
Certified Pre-Owned: No
Listed since: 06-07-2025 - Price Drop$25,987good price$1,314 below market
- 29,123 miles
- 1 accident, 1 owner, corporate fleet vehicle
- 5 Seats, 18 City / 24 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Coon Rapids, MN / 1,062 miles away from Chesapeake, VA
CarFax 1-Owner,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Hands-Free Liftgate,Heated Seats,Heated Steering Wheel,Keyless S...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 1C4PJMBX8ND517172
Stock: PND517172
Certified Pre-Owned: Yes - $22,999good price$1,766 below market
- 51,463 miles
- No accidents, 2 owners, rental vehicle
- 5 Seats, 18 City / 24 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
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Located in Morgantown, WV / 282 miles away from Chesapeake, VA
Transfer of vehicle from another location to your neighborhood Enterprise Car Sales may require payment of a non-refundable transfer fee to begin the ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
21 Combined MPG (18 City/24 Highway)
Listing Information:
VIN: 1C4PJMBX8ND527894
Stock: 8FNP5C
Certified Pre-Owned: No
Listed since: 06-24-2025
Showing 379 - 399 out of 1,638 listings
Consumer Reviews for the Jeep Cherokee
Read recent reviews for the Jeep Cherokee
My new Jeep
bmwcharlie, 02/01/2021
2021 Jeep Cherokee Limited 4dr SUV (3.2L 6cyl 9A)
Time for a new lease as my Tiguan went back. I looked at a new Tiguan, Subaru Outback, Jeep Cherokee and the Volvo X 40. I chose the Jeep Cherokee.
The Jeep felt the most substantial by far. I was surprised by the cheap plastic center in the Subaru and the Volvo. The Tiguan was all plastic but for 289.00 a month all in (including all taxes and fees) the Tiguan Se was the least … expensive vehicle I have ever leased. The same equipped Tiguan was 370.00 a month. I really missed the heated steering wheel from my previous BMW so it was a must for my new lease. A Tiguan with a heated steering wheel was 407.00 a month. I set out for a new compact SUV for 350.00 a month. I never thought of leasing a Jeep but in my budget it kept coming up so I test drove it. I knew instantly this would be my next vehicle. I leased a Jeep Cherokee V6 Limited with Elite Pkg. for 381.00 a month including taxes and all fees. This was the most equipped car I ever had. Cooled seats front and back it even can parallel park. I love the remote start which automatically turns on the heated seats and steering wheel. This Jeep is on par with my X3. Which was 500.00 a month a new one 700. a month to lease. Value wise this is the best vehicle you will find. It took months of tracking prices and negotiating for me to get this price.
The Jeep ride is great, acceleration is great too. The Volvo was slightly better but the Jeep was pretty close. It rides more like the X3. The info entertainment is easy to use intuitive and fast which really makes for a great driving experience. The Jeep is compact unlike the Tiguan which felt like you had so much space in the cabin. Handling is sharp seats are comfortable. Since it mainly me and one other person most of the time I can live with the snug cabin. I took Delivery at the end of November and have had no problems. Fit and finish is great so I am thinking it should be pretty reliable.
Update: I still love my Cherokee. The Adaptive cruise control is amazing. Life changing feature. The stop and go really takes the sting out of heavy traffic. The automatic high beams are amazing. The ride is great it really takes any size pot hole no problem. Well not quite the razor sharp handle of a BMW it’s much more comfortable. The ride, handling, and acceleration strike a great balance. The lane keep assist is the cars big down fall. It’s will pull slightly at the wheel for no reason. Less on the highway than around town. It feels like you hit a piece of ice. I doesn’t bother me as much now but at first it was annoying as hell. I tried to disable it but couldn’t. I just put it on the lowest setting. Hopefully they will use a lane centering on the next update. The car feels so high tech it’s quite unexpected.. I am so glad I got this Jeep. I would have never considered it, if not for the chip shortage. Inventories were starting to get tight and they had the inventory. I got this lease at such a great deal.I am so grateful as prices are skyrocketing on leases. Blown away by the luxury driving experience from a Jeep, Who knew!
Used 2020 Jeep Cherokee in Chesapeake, VA Values
Estimated values
2020 Jeep Cherokee High Altitude 4dr SUV 4WD (2.0L 4cyl Turbo 9A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $18,322 | $20,338 | $22,278 |
| Clean | $17,848 | $19,805 | $21,687 |
| Average | $17,057 | $18,917 | $20,703 |
| Rough | $16,029 | $17,762 | $19,422 |
The average list price of a used 2020 Jeep Cherokee in Chesapeake, Virginia is $21,752. The average mileage on a used Jeep Cherokee 2020 for sale in Chesapeake, Virginia is 51,456. Based on the average mileage of 51,456 for used 2020 Jeep Cherokee for sale in Chesapeake, VA and using an average vehicle condition rating, which means the vehicle may have a few mechanical and/or cosmetic problems and may require a considerable amount of reconditioning, we appraise the average trade-in value of a used Jeep Cherokee 2020 in Chesapeake, Virginia to be $17,057.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.