Skip to FiltersReport abuse
2,034 listings
- $34,599fair price$591 above market
- 61,149 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Recharged (95 mi away)
Close
Located in Richmond, VA / 95 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH4NS239177
Stock: 239177
Certified Pre-Owned: No - Price Drop$30,238great price$3,736 below market
- 50,557 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Tampa, FL / 700 miles away from Chesapeake, VA
CarFax No Accidents Reported,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keepi...
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: 5TDHZRBH8MS554390
Stock: MS554390T
Certified Pre-Owned: No - Price Drop$25,987great price$2,656 below market
- 72,534 miles
- No accidents, 2 owners, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Liberty Ford of Fayetteville (190 mi away)
Close
Located in Fayetteville, NC / 190 miles away from Chesapeake, VA
2021 Toyota Highlander L Clean CARFAX | 72,400 Miles | Bold, Capable, and Family-ReadyIf you're looking for a dependable, feature-packed SUV with s...
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: 5TDCZRBH0MS537707
Stock: AMS537707
Certified Pre-Owned: No
Listed since: 07-17-2025 - $19,999fair price$276 above market
- 138,496 miles
- 2 accidents, 2 owners, personal use
- 8 Seats, 20 City / 26 Hwy MPG
- Ultimate Auto (150 mi away)
Close
Located in Temple Hills, MD / 150 miles away from Chesapeake, VA
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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH8JS904799
Stock: 10312
Certified Pre-Owned: No - New Listing$37,999great price$3,093 below market
- 18,060 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Sheehy Nissan Glen Burnie (170 mi away)
Close
Located in Glen Burnie, MD / 170 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDJZRBH7MS134931
Stock: E12381P
Certified Pre-Owned: No
Listed since: 08-01-2025 - New Listing$23,000great price$2,253 below market
- 98,123 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Capital Lincoln of Wilmington (195 mi away)
Close
Located in Wilmington, NC / 195 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH8KS586023
Stock: L250188A
Certified Pre-Owned: No
Listed since: 06-07-2025 - $19,577great price
- 80,015 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 20 City / 24 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Corpus Christi, TX / 1,386 miles away from Chesapeake, VA
CarFax 1-Owner,3rd Row Seat,Back-Up Camera,Bluetooth,Brake Assist,Lane Keeping Assist,Power Door Locks,Brake Assist,Front Wheel Drive,Gasoline Fuel,CD...
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:
22 Combined MPG (20 City/24 Highway)
Listing Information:
VIN: 5TDZARFH4KS052883
Stock: KS052883T
Certified Pre-Owned: No - Price Drop$30,398good price$2,283 below market
- 55,253 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- First Team Subaru Norfolk (9 mi away)
Close
Located in Norfolk, VA / 9 miles away from Chesapeake, VA
Silver 2023 Toyota Highlander L FWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hpThe 2023 Toyota Highlander LE is a popular ...
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/29 Highway)
Listing Information:
VIN: 5TDKDRAH5PS502757
Stock: NB1635
Certified Pre-Owned: No
Listed since: 06-23-2025 - Price Drop$39,329good price$2,149 below market
- 18,410 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Reidsville Nissan (194 mi away)
Close
Located in Reidsville, NC / 194 miles away from Chesapeake, VA
Your Next Ride Starts Here at Reidsville Nissan!Clean CARFAX. CARFAX One-Owner. Maroon 2023 Toyota Highlander XLE AWD 8-Speed Automatic 2.4L I4 PDI T...
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH4PS040657
Stock: R13446
Certified Pre-Owned: No
Listed since: 06-23-2025 - Price Drop$40,590fair price$814 below market
- 18,829 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 28 Hwy MPG
- Carvana - Richmond (100 mi away)
- Home delivery*
Close
Located in Richmond, VA / 100 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:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH8PS520362
Stock: 2003776743
Certified Pre-Owned: No
Listed since: 06-25-2025 - New Listing$29,595great price$4,808 below market
- 43,677 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 21 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Van Nuys, CA / 2,363 miles away from Chesapeake, VA
Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Chrome Wheels,Hands-Free Liftgate,Heated Seats,Heated St...
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: 5TDYZRAH7MS521818
Stock: MS521818P
Certified Pre-Owned: No - $19,995great price$2,076 below market
- 99,047 miles
- 1 accident, 2 owners, corporate fleet vehicle
- 7 Seats, 20 City / 26 Hwy MPG
- Imperial Highline (157 mi away)
Close
Located in Manassas, VA / 157 miles away from Chesapeake, VA
KEY FEATURES AND OPTIONS Comes equipped with: Rear Air Conditioning, Sunroof, Bluetooth, Navigation System. This Toyota Highlander also includes Clock...
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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH7HS434484
Stock: 34484
Certified Pre-Owned: No
Listed since: 10-22-2024 - Price Drop$32,207good price$2,182 below market
- 11,004 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Atlantic Auto & Truck Sales (9 mi away)
Close
Located in Virginia Beach, VA / 9 miles away from Chesapeake, VA
The 2021 Toyota Highlander LE offers a robust and comfortable driving experience, thanks to its powerful V6 engine and smooth ride quality. It also pr...
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: 5TDBZRBHXMS547754
Stock: 1311A
Certified Pre-Owned: No
Listed since: 07-22-2025 - Price Drop$23,590good price$1,388 below market
- 105,636 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Cincinnati, OH / 480 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFHXKS609513
Stock: 2003852771
Certified Pre-Owned: No
Listed since: 06-25-2025 - New Listing$32,000great price$2,938 below market
- 73,436 miles
- 7 Seats, 21 City / 29 Hwy MPG
- Bayside Ford (114 mi away)
Close
Located in King George, VA / 114 miles away from Chesapeake, VA
Toyota quality loaded with many features and priced to move from day #1!!! 3rd row seating, leather interior, panoramic sunroof and so many more optio...
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDFZRAH5MS063915
Stock: MS063915
Certified Pre-Owned: No
Listed since: 06-11-2025 - $29,798good price$3,407 below market
- 75,157 miles
- No accidents, 1 owner, corporate fleet vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- INFINITI of Suitland (149 mi away)
Close
Located in Suitland, MD / 149 miles away from Chesapeake, VA
2023 Toyota Highlander L Midnight Black AWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hpAWD.CARFAX One-Owner. Clean CARF...
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:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH5PS502997
Stock: B40096
Certified Pre-Owned: No
Listed since: 04-10-2025 - $32,495great price$1,998 below market
- 83,898 miles
- No accidents, 1 owner, corporate fleet vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Preston Chevrolet of Aberdeen (192 mi away)
Close
Located in Aberdeen, MD / 192 miles away from Chesapeake, VA
20/27 City/Highway MPGFounded in 1975, Preston has been providing a friendly, no-hassle car buying experience for more than 45 years. We have been fam...
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: 5TDFZRBH8MS101913
Stock: AP1011
Certified Pre-Owned: No
Listed since: 02-17-2025 - $16,990great price$1,635 below market
- 162,265 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 21 City / 27 Hwy MPG
- Apex Car & Truck Sales (161 mi away)
Close
Located in Apex, NC / 161 miles away from Chesapeake, VA
LIKE NEW ONE OWNER HIGHLANDER! Do not miss this excellent condition well maintained and well equipped 2019 Toyota Highlander XLE this versatile mid-si...
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 (21 City/27 Highway)
Listing Information:
VIN: 5TDKZRFH1KS336272
Stock: 336272
Certified Pre-Owned: No
Listed since: 06-02-2025 - $18,605fair price$54 below market
- 141,768 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 27 Hwy MPG
- Bayside Pre-Owned Super Center Hollywood (113 mi away)
Close
Located in Hollywood, MD / 113 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:
23 Combined MPG (21 City/27 Highway)
Listing Information:
VIN: 5TDKZRFH1HS525433
Stock: HS525433B
Certified Pre-Owned: No
Listed since: 06-27-2025 - Price Drop$22,990good price$1,218 below market
- 110,269 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
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: 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 (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH6KS610061
Stock: 2003831711
Certified Pre-Owned: No
Listed since: 06-19-2025 - Price Drop$24,250great price$2,290 below market
- 82,916 miles
- 1 accident, 3 owners, corporate fleet vehicle
- 7 Seats, 21 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Knoxville, TN / 436 miles away from Chesapeake, VA
3rd Row Seat,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Chrome Wheels,Heated Seats,Keyless Start,Lane Keeping Assist,Leather Seats,Navig...
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:
23 Combined MPG (21 City/27 Highway)
Listing Information:
VIN: 5TDYZRFH7KS360649
Stock: KS360649P
Certified Pre-Owned: No
Showing 337 - 357 out of 2,034 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
"Some Adjustment Needed"
Bill, 01/11/2020
2020 Toyota Highlander Limited 4dr SUV (3.5L 6cyl 8A)
Test drove the 2020 Limited. V-6 engine was responsive and ride was very quiet. Very good standard technology and driving safety packages. Interior had quality materials and good fit and finish. Second row captains chair seats are comfortable with plenty of room behind first row, third row seats useless except for small children which you would want in second row. Big disappointment … was drivers seat height adjustment; you better be 5'4" or above to have clear visibility over steering wheel and dash. Also, passenger seat has NO height adjustment; passengers 6'3" or above will be at or close to the ceiling. Except for the lack of adequate front seat height adjustments, I loved the car.
Used 2022 Toyota Highlander in Chesapeake, VA Values
Estimated values
2022 Toyota Highlander XLE 4dr SUV AWD (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $29,675 | $31,657 | $33,726 |
| Clean | $29,177 | $31,101 | $33,107 |
| Average | $28,346 | $30,175 | $32,077 |
| Rough | $27,267 | $28,970 | $30,738 |
The average list price of a used 2022 Toyota Highlander in Chesapeake, Virginia is $27,821. The average mileage on a used Toyota Highlander 2022 for sale in Chesapeake, Virginia is 76,214. Based on the average mileage of 76,214 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 $28,346.
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.