Skip to FiltersReport abuse
2,230 listings
- Price Drop$33,322fair price$525 below market
- 65,716 miles
- No accidents, 2 owners, rental vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Doug Henry Chevrolet Buick GMC (110 mi away)
Close
Located in Farmville, NC / 110 miles away from Chesapeake, VA
Doug Henry of Farmville believes in displaying an upfront low competitive price that is eligible for everyone in the general public. You qualify for t...
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: Yes
Features and Specs:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDGZRAH7NS539281
Stock: G8241A
Certified Pre-Owned: No
Listed since: 04-26-2025 - Price Drop$36,998great price$3,185 below market
- 33,849 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from GA to VA*
Close
Located in Bogart, GA / 452 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: 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH4NS236361
Stock: 27361094
Certified Pre-Owned: No - $39,998good price$1,304 below market
- 19,874 miles
- 1 accident, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from NV to VA*
Close
Located in Las Vegas, NV / 2,153 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: 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: Yes
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDDZRBH7NS187515
Stock: 26902449
Certified Pre-Owned: No - $30,795good price
- 62,412 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in San Antonio, TX / 1,392 miles away from Chesapeake, VA
CarFax 1-Owner,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keeping Assist,Remo...
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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDGZRAH8NS115219
Stock: NS115219P
Certified Pre-Owned: No - Price Drop
- 24,175 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from WA to VA*
Close
Located in Vancouver, WA / 2,449 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDFZRBH7NS233076
Stock: 27271601
Certified Pre-Owned: No - New Listing$36,999fair price$757 above market
- 52,560 miles
- 7 Seats, 20 City / 27 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Stockton, CA / 2,450 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 Unavailable.
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH2NS585082
Stock: 8D9HRX
Certified Pre-Owned: No
Listed since: 04-22-2025 - New Listing$39,998good price$1,458 below market
- 27,614 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from OK to VA*
Close
Located in Norman, OK / 1,190 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: 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDJZRBH4NS199382
Stock: 27085187
Certified Pre-Owned: No - $28,995good price$1,629 below market
- 55,880 miles
- 1 accident, 2 owners, personal use only
- 8 Seats, 21 City / 29 Hwy MPG
- Ourisman Chantilly Toyota (164 mi away)
Close
Located in Chantilly, VA / 164 miles away from Chesapeake, VA
OURISMAN CERTIFIED! Enjoy peace of mind with a 12-month or/ 12,000-mile limited comprehensive warranty and a 7-year or/100,000-mile (on the odometer) ...
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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDCZRAH3NS557422
Stock: DA10511
Certified Pre-Owned: No
Listed since: 04-30-2025 - New Listing$30,213good price$1,297 below market
- 57,957 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- DARCARS Toyota of Baltimore (177 mi away)
Close
Located in Baltimore, MD / 177 miles away from Chesapeake, VA
2020 Toyota Highlander XLE Recent Arrival! CARFAX One-Owner.AWD, Radio: Premium Audio w/Navigation, 18" Machined Alloy Wheels, 3.003 Axle Ratio, 3rd...
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/27 Highway)
Listing Information:
VIN: 5TDHZRBH7LS049858
Stock: 52E8523A
Certified Pre-Owned: No
Listed since: 06-07-2025 - $25,500fair price$125 above market
- 77,844 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Koons Annapolis Toyota (155 mi away)
Close
Located in Annapolis, MD / 155 miles away from Chesapeake, VA
18" Painted Alloy Wheels, 3.003 Axle Ratio, 3rd row seats: split-bench, 4-Wheel Disc Brakes, 6 Speakers, ABS brakes, Air Conditioning, Alloy wheels, 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDBZRBH9LS048331
Stock: KAT250225A
Certified Pre-Owned: No
Listed since: 06-05-2025 - $29,999fair price$7 above market
- 55,440 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 29 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Bloomington, CA / 2,307 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: 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDZZRAH5NS119365
Stock: 8DWT7Y
Certified Pre-Owned: No
Listed since: 04-30-2025 - 26,156 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in West Allis, WI / 760 miles away from Chesapeake, VA
CarFax No Accidents Reported,CarFax 1-Owner,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Keyless Start,Lane Kee...
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/27 Highway)
Listing Information:
VIN: 5TDBZRBH4NS588348
Stock: F92620
Certified Pre-Owned: No- Price Drop
- 25,899 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from WA to VA*
Close
Located in Vancouver, WA / 2,449 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDFZRBH0NS230262
Stock: 27271527
Certified Pre-Owned: No - $38,999fair price$100 above market
- 51,810 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Henderson, NV / 2,144 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDDZRBH2NS251752
Stock: 7VH286
Certified Pre-Owned: No
Listed since: 04-30-2025 - New Listing$32,988fair price
- 29,414 miles
- No accidents, 1 owner, personal use
- 8 Seats, 21 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Frisco, TX / 1,186 miles away from Chesapeake, VA
Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Remote Start,Satellite...
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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDZZRAH8NS127444
Stock: NS127444A
Certified Pre-Owned: No - $38,998fair price$393 above market
- 28,263 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to VA*
Close
Located in Escondido, CA / 2,311 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: 5TDJZRAH7NS117873
Stock: 27136806
Certified Pre-Owned: No - New Listing$37,999fair price$707 above market
- 28,311 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- King Kia (176 mi away)
Close
Located in Gaithersburg, MD / 176 miles away from Chesapeake, VA
***2022 Toyota Highlander XLE***CARFAX 1-OWNER***LOCAL TRADE***AWD***APP CONNECT***REAR VIEW CAMERA*** **BLIND SPOT MONITOR*** Highlander XLE, 8-Speed...
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/27 Highway)
Listing Information:
VIN: 5TDGZRBH3NS582692
Stock: KS582692
Certified Pre-Owned: No
Listed since: 06-02-2025 - 21,520 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Wayne, NJ / 309 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: 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/27 Highway)
Listing Information:
VIN: 5TDGZRBH8NS568884
Stock: 8GHLXP
Certified Pre-Owned: No
Listed since: 04-18-2025- New Listing$37,998fair price$172 above market
- 28,812 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from NH to VA*
Close
Located in Manchester, NH / 499 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/27 Highway)
Listing Information:
VIN: 5TDGZRBH1NS172294
Stock: 27449662
Certified Pre-Owned: No - Price Drop$38,499good price$872 below market
- 29,705 miles
- 2 accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- DARCARS Nissan of Rockville (172 mi away)
Close
Located in Rockville, MD / 172 miles away from Chesapeake, VA
2022 Toyota Highlander XSE Celestial Silver Metallic 3.5L V6 DOHC 8-Speed Automatic AWD**CARFAX ONE OWNER**BALANCE OF FACTORY WARRANTY**AWD**POWER SUN...
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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDLZRBH0NS197248
Stock: P1L0588
Certified Pre-Owned: No
Listed since: 05-22-2025 - Price Drop
- 29,600 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from WA to VA*
Close
Located in Vancouver, WA / 2,449 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDFZRBH3NS162037
Stock: 27434061
Certified Pre-Owned: No
Showing 379 - 399 out of 2,230 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
Rolling again
Ken S, 10/28/2021
2022 Toyota Highlander Limited 4dr SUV AWD (3.5L 6cyl 8A)
Just replaced a 2018 Highlander due to accident. Of course the car is comfortable and nice to drive but I especially appreciate it after the accident. The 2018 was totaled because of a head on collision. My wife and I only had minor injuries that I attribute to the strength of the vehicle and the air bags that completely isolated us.
Used 2022 Toyota Highlander in Chesapeake, VA Values
Estimated values
2022 Toyota Highlander XLE 4dr SUV (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $31,411 | $33,595 | $35,875 |
| Clean | $30,883 | $33,005 | $35,218 |
| Average | $30,004 | $32,022 | $34,122 |
| Rough | $28,861 | $30,743 | $32,697 |
The average list price of a used 2022 Toyota Highlander in Chesapeake, Virginia is $36,840. The average mileage on a used Toyota Highlander 2022 for sale in Chesapeake, Virginia is 39,658. Based on the average mileage of 39,658 for used 2022 Toyota Highlander 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 Toyota Highlander 2022 in Chesapeake, Virginia to be $30,004.
Filters
Skip to ResultsApplied Filters4Active
Make & Model
Year
New / Used
Price & Payments
Price Rating
Body Type
Trim
Mileage
Accidents & History
Engine & Drivetrain
Exterior Color
Interior Color
Total Seating
Edmunds Review
Features
Options & Packages
MPG
* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.