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2,223 listings
- New Listing
- 14,646 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from FL to VA*
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Located in Daytona Beach, FL / 593 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH9PS029509
Stock: 26959296
Certified Pre-Owned: No - New Listing
- 14,974 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 28 Hwy MPG
- CarMax (In-stock online)
- Transfer available from OH to VA*
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Located in Cincinnati, OH / 485 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:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH4PS515160
Stock: 26484353
Certified Pre-Owned: No - 16,777 miles
- No accidents, personal use only
- 8 Seats, 21 City / 28 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Casper, WY / 1,635 miles away from Chesapeake, VA
CarFax No Accidents Reported,Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Satellite Ra...
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: 5TDKDRBH3PS140099
Stock: 8534CF
Certified Pre-Owned: No- New Listing$40,998fair price$737 above market
- 16,000 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from FL to VA*
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Located in Pompano Beach, FL / 759 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH1PS519006
Stock: 27324170
Certified Pre-Owned: No - New Listing
- 16,417 miles
- No accidents, 1 owner, personal use
- 7 Seats, 22 City / 29 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Atlanta, GA / 506 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH5PS021312
Stock: 2003786140
Certified Pre-Owned: No
Listed since: 06-10-2025 - New Listing$37,590great price
- 31,230 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 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: 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: 5TDKDRAH4RS531217
Stock: 2003628005
Certified Pre-Owned: No
Listed since: 04-17-2025 - New Listing$42,998fair price$1,138 above market
- 16,889 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from FL to VA*
Close
Located in Pompano Beach, FL / 759 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH5PS029135
Stock: 27461398
Certified Pre-Owned: No - New Listing$39,999fair price$56 below market
- 31,361 miles
- 7 Seats, 21 City / 28 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
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Located in New Rochelle, NY / 317 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:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH3PS029777
Stock: 8DYJSV
Certified Pre-Owned: No
Listed since: 05-30-2025 - Price Drop
- 38,608 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Hall Toyota Virginia Beach (13 mi away)
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Located in Virginia Beach, VA / 13 miles away from Chesapeake, VA
Celestial Silver Metallic 2021 Toyota Highlander Platinum AWD 8-Speed Automatic 3.5L V6 DOHC AWD.AWD, 11 Speakers, 20" Painted Alloy Wheels, 3.003 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: 5TDFZRBH0MS100478
Stock: 24255595A
Certified Pre-Owned: No
Listed since: 05-31-2025 - Price Drop$39,998fair price$578 above market
- 18,954 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from NV to VA*
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Located in Reno, NV / 2,352 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH0PS513102
Stock: 27420382
Certified Pre-Owned: No - Price Drop
- 21,061 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Charlotte, NC / 277 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH6PS008715
Stock: 2003773528
Certified Pre-Owned: No
Listed since: 05-30-2025 - 28,808 miles
- 2 accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Lucky Line Motors (127 mi away)
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Located in Fredericksburg, VA / 127 miles away from Chesapeake, VA
***** WE FINANCE ***** 2021 TOYOTA HIGHLANDER LE ONE OWNER CARFAX / VEHICLE LOADED WITH PREMIUM SOUND SYSTEM / AUX PORT / BLUETOOTH CONNECTION/ BACKUP...
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: Yes
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDBZRBHXMS153767
Stock: LLM11887
Certified Pre-Owned: No- New Listing
- 19,690 miles
- No accidents, 1 owner, corporate fleet vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Buffalo, NY / 443 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: 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: 5TDKDRBHXPS522940
Stock: 2003772375
Certified Pre-Owned: No
Listed since: 06-06-2025 - 36,833 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 28 Hwy MPG
- Pearson Toyota (34 mi away)
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Located in Newport News, VA / 34 miles away from Chesapeake, VA
2023 Toyota Highlander XSE 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp AWD WhiteAWD.21/28 City/Highway MPGWe offer Market Based Pricing, so p...
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: 5TDKDRBH3PS018746
Stock: 17211A
Certified Pre-Owned: No
Listed since: 05-24-2025- 37,123 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Classic Toyota Hampton (23 mi away)
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Located in Hampton, VA / 23 miles away from Chesapeake, VA
Moon Dust 2023 Toyota Highlander XLEOdometer is 5536 miles below market average!** SPECIAL LARGE 12.3-IN SCREEN ** **FREE OIL CHANGES AND STATE INSPEC...
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: 5TDKDRAH2PS041016
Stock: PPS041016
Certified Pre-Owned: No
Listed since: 04-24-2025- New Listing
- 25,747 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Miami, FL / 796 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH9PS008143
Stock: 2003743926
Certified Pre-Owned: No
Listed since: 05-26-2025 - New Listing
- 32,528 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Carvana - Richmond (99 mi away)
- Home delivery*
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Located in Richmond, VA / 99 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDHZRBH6MS061453
Stock: 2003705610
Certified Pre-Owned: No
Listed since: 05-10-2025 - 26,695 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from AZ to VA*
Close
Located in Tolleson, AZ / 2,038 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH1PS041573
Stock: 27450995
Certified Pre-Owned: No- New Listing
- 13,836 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Hendrick Toyota Apex (160 mi away)
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Located in Apex, NC / 160 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 (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH6PS049748
Stock: S59217A
Certified Pre-Owned: No
Listed since: 06-10-2025 - Price Drop$38,990fair price$575 above market
- 30,949 miles
- No accidents, 3 owners, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Phoenix, AZ / 2,024 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: 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: 5TDKDRAH1PS003518
Stock: 2003746543
Certified Pre-Owned: No
Listed since: 06-05-2025 - New Listing
- 58,731 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Hall Honda Elizabeth City (31 mi away)
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Located in Elizabeth City, NC / 31 miles away from Chesapeake, VA
Blizzard Pearl 2021 Toyota Highlander XLE AWD 8-Speed Automatic 3.5L V6 DOHC We are currently offering Vehicle Purchase Home Delivery by appointment. ...
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: 5TDHZRBH2MS107831
Stock: 2252260B
Certified Pre-Owned: No
Listed since: 06-11-2025
Showing 421 - 441 out of 2,223 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
Love the vehicle, Infotainment is unusable
bbells, 04/16/2023
2023 Toyota Highlander LE 4dr SUV (2.4L 4cyl Turbo 8A)
Love the gas mileage, 30+mpg in eco mode. Towing capacity. Comfort. Nice vehicle except the "drive connect" app advertisement makes the entertainment system unusable. It will lock up the system for 1 to 10 minutes so no music, no google maps, no phone, nothing, until it decides to clear itself. Toyota says you can pay $200 a year to remove the advertisement by subscribing to drive … connect. This makes it the definition of ransomware. But there is nothing in the app I need or want. Neither ToyotaUSA, their tech department, or the dealer can fix it. I will either be selling the vehicle or replacing the entertainment system when the free trial of drive connect ends in a couple months. For those of us who use their phone for maps, texts or communication the system makes the vehicle unusable. Update: Can't put in different infotainment system, it is integrated into the vehicle. Toyota gave me a free trial of drive connect. Unfortunately anytime i am in an area without internet the display is locked up asking for a password. Can't enter a password until i get into an internet area, then go s back to asking for a password when i leave it. Worthless and unusable. Toyota wouldn't fix it. After 7 months they bought it back from me. Last Toyota.
Used 2023 Toyota Highlander in Chesapeake, VA Values
Estimated values
2023 Toyota Highlander Platinum 4dr SUV (2.4L 4cyl Turbo 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $40,715 | $42,946 | $45,460 |
| Clean | $40,205 | $42,363 | $44,795 |
| Average | $39,355 | $41,391 | $43,687 |
| Rough | $38,250 | $40,127 | $42,246 |
The average list price of a used 2023 Toyota Highlander in Chesapeake, Virginia is $41,383. The average mileage on a used Toyota Highlander 2023 for sale in Chesapeake, Virginia is 26,088. Based on the average mileage of 26,088 for used 2023 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 2023 in Chesapeake, Virginia to be $39,355.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.