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2,192 listings
- $45,500fair price$213 above market
- 25,434 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 28 Hwy MPG
- Jim Coleman Honda (175 mi away)
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Located in Clarksville, MD / 175 miles away from Chesapeake, VA
Certified. Toyota Gold Certified Details:* Powertrain Limited Warranty: 84 Month/100,000 Mile (whichever comes first) from TCUV purchase date* Vehicle...
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: 5TDKDRBH0PS517682
Stock: PX9623
Certified Pre-Owned: No
Listed since: 02-22-2025 - New Listing$38,990fair price$777 above market
- 20,357 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 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: 5TDKDRAHXPS505881
Stock: 2003667730
Certified Pre-Owned: No
Listed since: 05-16-2025 - Price Drop$43,998fair price$207 below market
- 21,014 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 Fort Myers, FL / 774 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: 5TDKDRAH1PS048040
Stock: 27313050
Certified Pre-Owned: No - $33,500good price$1,522 below market
- 52,318 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Antwerpen Toyota (175 mi away)
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Located in Clarksville, MD / 175 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: 5TDKDRAH9PS012337
Stock: 1739PR
Certified Pre-Owned: No
Listed since: 01-25-2025 - $38,998fair price
- 22,833 miles
- No accidents, 2 owners, rental vehicle
- 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: 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH4PS037419
Stock: 27057181
Certified Pre-Owned: No - New Listing$34,995fair price$776 below market
- 29,319 miles
- 8 Seats, 20 City / 27 Hwy MPG
- Auto Trademark (156 mi away)
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Located in Manassas, VA / 156 miles away from Chesapeake, VA
2021 Toyota Highlander XLE AWD Call 703-361-6882, 29K Miles Only, Balance Of Factory Warranty, 3rd Row, Adaptive Cruise Control, Lane Departure Warnin...
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDHZRBH4MS540812
Stock: AT17782
Certified Pre-Owned: No - New Listing$43,990fair price
- 24,348 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in San Antonio, TX / 1,380 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: 5TDKDRAH0PS523421
Stock: 2003774324
Certified Pre-Owned: No
Listed since: 06-06-2025 - $18,795good price$1,053 below market
- 153,237 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 21 City / 29 Hwy MPG
- Olympia Pre-Owned Auto (149 mi away)
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Located in Raleigh, NC / 149 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDCZRAH8MS044441
Stock: 044441
Certified Pre-Owned: No - New Listing$31,000good price$1,048 below market
- 63,376 miles
- No accidents, 3 owners, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Koons Tysons Chrysler Dodge Jeep Ram (160 mi away)
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Located in Vienna, VA / 160 miles away from Chesapeake, VA
Recent Arrival! 2021 Toyota Highlander XLE AWDAWD.Awards: * ALG Residual Value Awards, Residual Value AwardsPriced below KBB Fair Purchase Pri...
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: 5TDHZRBH9MS535203
Stock: J254003B
Certified Pre-Owned: No
Listed since: 06-08-2025 - $38,998fair price$1,066 below market
- 22,058 miles
- 1 accident, 1 owner, personal use
- 7 Seats, 21 City / 28 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CT to VA*
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Located in East Haven, CT / 362 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:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH2PS008189
Stock: 27449974
Certified Pre-Owned: No - $30,500good price$1,996 below market
- 42,178 miles
- 1 accident, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Las Vegas, NV / 2,153 miles away from Chesapeake, VA
CarFax 1-Owner,Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Satellite Radio,Turbo/Supe...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH4PS503026
Stock: N503026P
Certified Pre-Owned: No - New Listing$32,198fair price$502 above market
- 53,579 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
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Located in Indianapolis, IN / 572 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: 5TDKDRAHXPS503211
Stock: 8DV6K3
Certified Pre-Owned: No
Listed since: 04-30-2025 - Price Drop$36,600fair price$946 above market
- 47,375 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- First Team Toyota (14 mi away)
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Located in Chesapeake, VA / 14 miles away from Chesapeake, VA
Clean CARFAX. ABS brakes, Active Cruise Control, Alloy wheels, Electronic Stability Control, Front dual zone A/C, Heated door mirrors, Heated Front Bu...
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: 5TDKDRAH3PS011930
Stock: TB13140
Certified Pre-Owned: No
Listed since: 04-23-2025 - Price Drop$36,500good price$1,542 below market
- 54,475 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- John Hiester Chevrolet (160 mi away)
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Located in Fuquay Varina, NC / 160 miles away from Chesapeake, VA
ONE OWNER, LIFETIME ENGINE GUARANTEE, POWER SUNROOF/MOONROOF, HEATED SEATS, REAR BACKUP CAMERA, Bluetooth HANDS FREE, LEATHER, FAST AND EASY FINANCI...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH3PS023429
Stock: B10698A
Certified Pre-Owned: No
Listed since: 04-24-2025 - $40,998fair price
- 28,757 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to VA*
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Located in El Paso, TX / 1,745 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: 5TDKDRAH7PS025085
Stock: 26102826
Certified Pre-Owned: No - $38,998fair price$590 above market
- 29,144 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- CarMax Laurel (168 mi away)
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Located in Laurel, MD / 168 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: 5TDDZRBH4MS527007
Stock: 27379089
Certified Pre-Owned: No - Price Drop
- 30,408 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- CarMax (In-stock online)
- Transfer available from UT to VA*
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Located in South Jordan, UT / 1,929 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/28 Highway)
Listing Information:
VIN: 5TDKDRBH8PS512388
Stock: 27214326
Certified Pre-Owned: No - $36,000fair price$727 above market
- 37,459 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Haley Certified Preowned (90 mi away)
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Located in Richmond, VA / 90 miles away from Chesapeake, VA
*Vehicle pricing excludes tax, title, tags, $799 processing fee, and $319 fee for theft protection etch.*
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: 5TDHZRBH4MS554421
Stock: J6884
Certified Pre-Owned: No
Listed since: 05-22-2025 - New Listing$42,998fair price
- 30,453 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to VA*
Close
Located in Pharr, TX / 1,479 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: 5TDKDRAH3PS034060
Stock: 27424519
Certified Pre-Owned: No - Price Drop
Photos not available$37,495good price$934 below market- 37,480 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Rick Hendrick Toyota (192 mi away)
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Located in Fayetteville, NC / 192 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: 5TDKDRAH1PS005866
Stock: S31319A
Certified Pre-Owned: No
Listed since: 05-03-2025 - Price Drop$35,998good price$1,718 below market
- 37,060 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 22 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: 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH8PS025757
Stock: 27428498
Certified Pre-Owned: No
Showing 316 - 336 out of 2,192 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 AWD (2.4L 4cyl Turbo 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $36,504 | $38,321 | $40,368 |
| Clean | $36,046 | $37,801 | $39,777 |
| Average | $35,284 | $36,933 | $38,793 |
| Rough | $34,294 | $35,806 | $37,514 |
The average list price of a used 2023 Toyota Highlander in Chesapeake, Virginia is $37,193. The average mileage on a used Toyota Highlander 2023 for sale in Chesapeake, Virginia is 41,079. Based on the average mileage of 41,079 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 $35,284.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.