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2,090 listings
- $24,750good price$1,651 below market
- 99,693 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Koons Easton Toyota (138 mi away)
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Located in Easton, MD / 138 miles away from Chesapeake, VA
2021 Toyota Highlander LE 2021 Toyota Highlander LE in Blizzard Pearl, Please call 410-822-8000 with any equipment or availability questions!, Schedul...
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: 5TDBZRBH5MS089928
Stock: KET250059A
Certified Pre-Owned: No
Listed since: 05-05-2025 - $36,998fair price$280 below market
- 12,650 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 28 Hwy MPG
- CarMax (In-stock online)
- Transfer available from ID to VA*
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Located in Meridian, ID / 2,148 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: 5TDKDRBH5PS505916
Stock: 26833814
Certified Pre-Owned: No - New Listing$34,279fair price$192 below market
- 17,247 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Van Nuys, CA / 2,363 miles away from Chesapeake, VA
3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Remote Start,Satellite Radio,Tur...
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: 5TDKDRAH2PS512114
Stock: PS512114T
Certified Pre-Owned: No - Price Drop$35,488good price$2,294 below market
- 50,961 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Hubert Vester Honda (119 mi away)
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Located in Wilson, NC / 119 miles away from Chesapeake, VA
CARFAX One-Owner.Cypress 2023 Toyota Highlander XLE 4D Sport Utility FWD 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp 8-Speed AutomaticVester ...
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: 5TDKDRAHXPS501541
Stock: TP5782
Certified Pre-Owned: No
Listed since: 05-06-2025 - $38,999fair price$1,002 below market
- 49,496 miles
- No accidents, 2 owners, rental vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Enterprise Car Sales Raleigh (150 mi away)
- Home delivery*
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Located in Raleigh, NC / 150 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: 5TDFZRBH5MS072791
Stock: 8DWVMN
Certified Pre-Owned: No
Listed since: 04-29-2025 - $29,460fair price$489 below market
- 56,922 miles
- 1 accident, 2 owners, corporate fleet vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- Johnson Lexus of Raleigh (144 mi away)
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Located in Raleigh, NC / 144 miles away from Chesapeake, VA
JUST ARRIVED!! DETAILS COMING SOON!This vehicle is located at Johnson Lexus of Raleigh.Here at Johnson Lexus we price our cars online aggressively ...
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 (20 City/27 Highway)
Listing Information:
VIN: 5TDBZRBH0MS068131
Stock: D42298B
Certified Pre-Owned: No
Listed since: 04-26-2025 - Price Drop$33,990good price$1,974 below market
- 33,197 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Hendrick Toyota Wilmington (195 mi away)
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Located in Wilmington, NC / 195 miles away from Chesapeake, VA
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: 5TDKDRAH5PS505349
Stock: P8208
Certified Pre-Owned: Yes
Listed since: 11-19-2024 - New Listing$40,998good price
- 25,496 miles
- No accidents, 2 owners, personal use
- 7 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to VA*
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Located in San Antonio, TX / 1,370 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: 5TDKDRAH7PS040010
Stock: 27295522
Certified Pre-Owned: No - New Listing$42,998good price$1,224 below market
- 20,481 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from SC to VA*
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Located in Greenville, SC / 367 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: 5TDKDRAH8PS520248
Stock: 27446252
Certified Pre-Owned: No - New Listing$33,990fair price$534 below market
- 36,058 miles
- No accidents, 1 owner, corporate fleet vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Indianapolis, IN / 578 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: 5TDKDRBH3PS502125
Stock: 2003683276
Certified Pre-Owned: No
Listed since: 04-30-2025 - Price Drop$34,995good price$1,631 below market
- 27,063 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Hendrick Toyota Wilmington (195 mi away)
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Located in Wilmington, NC / 195 miles away from Chesapeake, VA
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: 5TDKDRAH4PS033807
Stock: P8207
Certified Pre-Owned: Yes
Listed since: 12-29-2024 - Price Drop$31,699good price$2,740 below market
- 48,880 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Sheehy Toyota of Fredericksburg (126 mi away)
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Located in Fredericksburg, VA / 126 miles away from Chesapeake, VA
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: 5TDKDRAH9PS501319
Stock: F9231R
Certified Pre-Owned: Yes
Listed since: 04-04-2025 - New Listing$30,998good price
- 32,914 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to VA*
Close
Located in San Antonio, TX / 1,370 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: 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: 5TDKDRAH5PS516089
Stock: 27424526
Certified Pre-Owned: No - Price Drop$37,900good price$1,908 below market
- 31,499 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 28 Hwy MPG
- Jim Coleman Toyota (166 mi away)
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Located in Bethesda, MD / 166 miles away from Chesapeake, VA
1 OWNER, CLEAN CARFAX, SUNROOF, HEATED FRONT SEATS, APPLE CARPLAY, ANDROID AUTO, REAR VIEW CAMERA, 3RD ROW SEATING, ALL WHEEL DRIVE.Red 2023 Toyota Hi...
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: 5TDKDRBH1PS030037
Stock: RT13253
Certified Pre-Owned: No
Listed since: 03-30-2025 - $34,050great price$2,911 below market
- 46,006 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Wesley Chapel, FL / 687 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: 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: 5TDKDRAH9PS038100
Stock: M038100T
Certified Pre-Owned: No - $37,999fair price
- 35,668 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Arlington, TX / 1,214 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAHXPS036761
Stock: 7WWPV8
Certified Pre-Owned: No
Listed since: 04-22-2025 - Price Drop$36,998good price$3,265 below market
- 29,905 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to VA*
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Located in Bakersfield, CA / 2,374 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: 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: 5TDKDRBH4PS042425
Stock: 27452448
Certified Pre-Owned: No - Price Drop$33,695fair price$393 above market
- 39,094 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Trust Auto (192 mi away)
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Located in Sykesville, MD / 192 miles away from Chesapeake, VA
You can find this Loaded 2021 Toyota Highlander XLE 7-Passenger SUV FWD (Front Wheel Drive) and many others like it at Trust Auto. This Toyota include...
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: 5TDGZRAHXMS044670
Stock: 044670
Certified Pre-Owned: No
Listed since: 04-22-2025 - $33,998fair price
- 23,181 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to VA*
Close
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH3PS031479
Stock: 27204988
Certified Pre-Owned: No - 22,516 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to VA*
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Located in Fresno, CA / 2,390 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: 5TDKDRAH4PS506251
Stock: 27122262
Certified Pre-Owned: No- $32,490good price$1,968 below market
- 99,921 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Driveway (150 mi away)
- Home delivery*
Close
Located in Springfield, VA / 150 miles away from Chesapeake, VA
CarFax No Accidents Reported,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Hands-Free Liftgate,Heated Seats,Heat...
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: 5TDFZRBH8MS137388
Stock: 24830P
Certified Pre-Owned: No
Showing 232 - 252 out of 2,090 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 2021 Toyota Highlander in Chesapeake, VA Values
Estimated values
2021 Toyota Highlander LE 4dr SUV AWD (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $27,927 | $30,241 | $32,561 |
| Clean | $27,332 | $29,582 | $31,835 |
| Average | $26,341 | $28,484 | $30,625 |
| Rough | $25,053 | $27,056 | $29,053 |
The average list price of a used 2021 Toyota Highlander in Chesapeake, Virginia is $35,275. The average mileage on a used Toyota Highlander 2021 for sale in Chesapeake, Virginia is 39,945. Based on the average mileage of 39,945 for used 2021 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 2021 in Chesapeake, Virginia to be $26,341.
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