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2,076 listings
- Price Drop$33,390good price$2,560 below market
- 61,115 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Westgate Chrysler Jeep Dodge Ram (152 mi away)
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Located in Raleigh, NC / 152 miles away from Chesapeake, VA
11 Speakers, 3.003 Axle Ratio, 3rd row seats: split-bench, 4-Wheel Disc Brakes, ABS brakes, Air Conditioning, Alloy wheels, AM/FM radio: SiriusXM, App...
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: 5TDYZRAH5NS103064
Stock: J42549A
Certified Pre-Owned: No
Listed since: 12-03-2024 - $42,395fair price$186 above market
- 21,693 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Fitzgerald Toyota Gaithersburg (176 mi away)
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Located in Gaithersburg, MD / 176 miles away from Chesapeake, VA
You won't want to miss this excellent value! Pure practicality in a stylish package. Turbocharger technology provides forced air induction, enhancing ...
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: 5TDKDRBH0RS544383
Stock: ER44383
Certified Pre-Owned: No
Listed since: 04-16-2025 - $36,600good price$1,970 below market
- 36,669 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Hall Toyota Elizabeth City (31 mi away)
- Home delivery*
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Located in Elizabeth City, NC / 31 miles away from Chesapeake, VA
We are currently offering Vehicle Purchase Home Delivery by appointment. Please contact for details.. Blueprint LE FWD 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH4RS547255
Stock: 22255037A
Certified Pre-Owned: No
Listed since: 03-18-2025 - Price Drop$31,997good price$2,195 below market
- 62,146 miles
- No accidents, 2 owners, rental vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- EchoPark Automotive Raleigh (155 mi away)
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Located in Cary, NC / 155 miles away from Chesapeake, VA
At EchoPark, it’s all about offering you options for a happy experience. We have thousands of new-to-you makes and models that range from sedans to tr...
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/29 Highway)
Listing Information:
VIN: 5TDGZRAH6NS549896
Stock: CNS549896
Certified Pre-Owned: No
Listed since: 05-13-2025 - Price Drop$39,695good price$1,882 below market
- 30,516 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Bill Page Toyota (157 mi away)
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Located in Falls Church, VA / 157 miles away from Chesapeake, VA
2024 Toyota Highlander LE Midnight Black AWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hpToyota Safety Sense 2.5+: Pre-Colli...
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: 5TDKDRBH3RS552056
Stock: P8512
Certified Pre-Owned: Yes
Listed since: 05-08-2025 - $37,998good price$2,015 below market
- 30,687 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- CarMax Greenville NC (105 mi away)
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Located in Winterville, NC / 105 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: 5TDHZRBH2NS583126
Stock: 27239600
Certified Pre-Owned: No - Price Drop$33,500fair price$548 below market
- 20,363 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Ourisman Honda of Tysons Corner (161 mi away)
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Located in Vienna, VA / 161 miles away from Chesapeake, VA
ONE OWNER, CLEAN CARFAX, FACTORY WARRENTY, BACKUP CAMERA / REAR VIEW CAMERA / REVERSE CAMERA, ADAPTIVE CRUISE CONTROL / ACC / DYNAMIC RADAR CRUISE CON...
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: 5TDBZRBH1NS205918
Stock: P205918
Certified Pre-Owned: No
Listed since: 05-19-2025 - Price Drop$36,000good price$1,177 below market
- 37,217 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Lexus of Towson (186 mi away)
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Located in Towson, MD / 186 miles away from Chesapeake, VA
CARFAX One-Owner. 2022 Toyota Highlander XLE Midnight Black Metallic AWD 8-Speed Automatic 3.5L V6 DOHCAWD, 3.003 Axle Ratio, 3rd row seats: split-ben...
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: 5TDGZRBH1NS567074
Stock: BT1610
Certified Pre-Owned: No
Listed since: 04-26-2025 - Price Drop$39,995good price$1,439 below market
- 28,549 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 28 Hwy MPG
- Waldorf Toyota (137 mi away)
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Located in Waldorf, MD / 137 miles away from Chesapeake, VA
**Recent Arrival!** **CLEAN Carfax!** **One Owner Vehicle!** **XLE!** **2024!** **AWD!** **Power Sunroof!** **Power Liftgate!** **Heated Seats!** **Fa...
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: 5TDKDRBH0RS536316
Stock: 00081299
Certified Pre-Owned: No
Listed since: 04-04-2025 - Price Drop$36,800good price$1,391 below market
- 29,192 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Heritage Toyota Owings Mills (187 mi away)
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Located in Owings Mills, MD / 187 miles away from Chesapeake, VA
Recent Arrival! **ALL WHEEL DRIVE**, **POWER DRIVERS SEAT**, **HEATED LEATHER SEATS**, **POWER SUNROOF**, **BACKUP CAMERA**, *APPLE CARPLAY/ANDROID AU...
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: 5TDGZRBH5NS566008
Stock: 7Z566008
Certified Pre-Owned: No
Listed since: 05-09-2025 - $43,500fair price$142 above market
- 15,883 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Hall Honda Virginia Beach (11 mi away)
- Five Star Dealer
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Located in Virginia Beach, VA / 11 miles away from Chesapeake, VA
Clean CARFAX. 2024 Toyota Highlander XLE AWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp AWD, ABS brakes, Active Cruise Con...
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: 5TDKDRBH7RS569149
Stock: 2252602A
Certified Pre-Owned: No
Listed since: 05-14-2025 - $41,276fair price$213 below market
- 25,359 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Jim McKay Chevrolet (158 mi away)
- Five Star Dealer
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Located in Fairfax, VA / 158 miles away from Chesapeake, VA
CARFAX One-Owner. 2024 Toyota Highlander XLE Wind Chill Pearl AWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp21/28 City/H...
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: 5TDKDRBH3RS571691
Stock: T250165A
Certified Pre-Owned: No
Listed since: 04-29-2025 - $39,795good price$694 below market
- 25,613 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Waldorf Toyota (137 mi away)
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Located in Waldorf, MD / 137 miles away from Chesapeake, VA
FREE 6MO/6K MILE TOYOTA LIMITED POWERTRAIN WARRANTY INCLUDED, ***In stock at WALDORF TOYOTA. Please call to confirm availability as inventory changes ...
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: 5TDJZRBH6NS219812
Stock: 00081394
Certified Pre-Owned: No
Listed since: 05-14-2025 - $35,443good price$1,147 below market
- 44,399 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Driveway (2 mi away)
- Home delivery*
Close
Located in Chesapeake, VA / 2 miles away from Chesapeake, VA
CarFax No Accidents Reported,CarFax 1-Owner,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Brake Assist,Heated Seats,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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH0NS231660
Stock: NS231660P
Certified Pre-Owned: No - Price Drop$37,388fair price$835 below market
- 21,859 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- Johnson Lexus of Durham (162 mi away)
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Located in Durham, NC / 162 miles away from Chesapeake, VA
PRICED WAY BELOW KBB RETAIL VALUE OF $40,056 FOR A QUICK AND HASSLE-FREE SALE! 1-OWNER TRADE-IN! ONLY 21,858 MILES! ACCIDENT-FREE CARFAX! AMAZING COND...
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: 5TDGZRAH3NS129481
Stock: DR30172A
Certified Pre-Owned: No
Listed since: 05-03-2025 - $30,871fair price$149 above market
- 91,010 miles
- No accidents, 1 owner, corporate fleet vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Exclusive Motor Cars (186 mi away)
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Located in Randallstown, MD / 186 miles away from Chesapeake, VA
This 2022 Black Toyota Highlander XLE FWD is well equipped and includes these features and benefits:. FWD 21/29 City/Highway MPG 21/29 City/Highway ...
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/29 Highway)
Listing Information:
VIN: 5TDGZRAH5NS104081
Stock: S104081
Certified Pre-Owned: No
Listed since: 04-15-2025 - Price Drop$41,500fair price$126 below market
- 19,004 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 28 Hwy MPG
- Ourisman Toyota 40 (187 mi away)
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Located in Edgewood, MD / 187 miles away from Chesapeake, VA
**Apple Car Play**Heated Seats**Leather**Moonroof**AWD**Clean CARFAX. 21/28 City/Highway MPG This 2024 Black Toyota Highlander XSE AWD is well equip...
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: 5TDKDRBH7RS540847
Stock: A2704
Certified Pre-Owned: No
Listed since: 05-19-2025 - Price Drop$40,590good price$1,274 below market
- 34,796 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Carvana - Richmond (100 mi away)
- Home delivery*
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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: 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: 5TDKDRAH4RS536384
Stock: 2003673857
Certified Pre-Owned: No
Listed since: 05-20-2025 - $27,995good price$1,020 below market
- 63,890 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Waldorf Toyota (137 mi away)
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Located in Waldorf, MD / 137 miles away from Chesapeake, VA
**Recent Arrival!** **Price Leader!** **AWD!** **Family Fun!** **Perfect For Any Commute!** **Ask For a Video Walk Around!*****In stock at WALDORF TOY...
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: 5TDCZRBH7NS587568
Stock: 00081308
Certified Pre-Owned: No - $37,750fair price$629 below market
- 18,826 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Koons Tysons Toyota (162 mi away)
- Five Star Dealer
Close
Located in Vienna, VA / 162 miles away from Chesapeake, VA
VEHICLE PROFESSIONALLY DETAILED, GOOD TIRES, GOOD BRAKES, RECENT TRADE, Highlander XLE, 4D Sport Utility, 3.5L V6 DOHC, Automatic, AWD, Apple CarPlay/...
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: 5TDGZRBHXNS167241
Stock: 0KW50749
Certified Pre-Owned: No
Listed since: 04-09-2025 - $46,990fair price$559 above market
- 8,675 miles
- No accidents, 1 owner, personal use only
- 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: 5TDKDRBH3RS529604
Stock: 2003726242
Certified Pre-Owned: No
Listed since: 05-21-2025
Showing 106 - 126 out of 2,076 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 2022 Toyota Highlander in Chesapeake, VA Values
Estimated values
2022 Toyota Highlander Limited 4dr SUV (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $35,578 | $37,939 | $40,404 |
| Clean | $34,981 | $37,273 | $39,663 |
| Average | $33,985 | $36,162 | $38,429 |
| Rough | $32,691 | $34,719 | $36,824 |
The average list price of a used 2022 Toyota Highlander in Chesapeake, Virginia is $37,689. The average mileage on a used Toyota Highlander 2022 for sale in Chesapeake, Virginia is 34,641. Based on the average mileage of 34,641 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 $33,985.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.