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2,162 listings
- New Listing$39,500good price$2,235 below market
- 29,311 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Capital Chevrolet (141 mi away)
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Located in Wake Forest, NC / 141 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: 5TDKDRAH9PS516113
Stock: 9C291562A
Certified Pre-Owned: No
Listed since: 06-01-2025 - New Listing$41,998fair price$110 below market
- 25,619 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to VA*
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Located in Roseville, CA / 2,439 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: 5TDKDRBH5PS026153
Stock: 27236517
Certified Pre-Owned: No - $31,999fair price$703 above market
- 55,039 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 Santa Clara, CA / 2,499 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: 5TDKDRAHXPS500079
Stock: 8DMJJ4
Certified Pre-Owned: No
Listed since: 04-24-2025 - New Listing$31,590good price$1,292 below market
- 52,853 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Salt Lake City, UT / 1,926 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: 5TDKDRBH6PS023746
Stock: 2003653191
Certified Pre-Owned: No
Listed since: 05-29-2025 - $40,998fair price$428 below market
- 32,269 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from MS to VA*
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Located in Saltillo, MS / 720 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: 5TDKDRAH1PS505915
Stock: 27092041
Certified Pre-Owned: No - $35,598fair price$266 below market
- 54,500 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
Celestial Silver Metallic 2023 Toyota Highlander XLE**FREE OIL CHANGES AND STATE INSPECTIONS GUARANTEED FOR LIFE! PARTS AND SERVICE GUARANTEED FOR LIF...
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: 5TDKDRAH6PS015695
Stock: PPS015695
Certified Pre-Owned: No
Listed since: 04-25-2025 - New Listing$31,990good price$1,189 below market
- 43,503 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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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: 5TDKDRAH7PS509256
Stock: 2003740951
Certified Pre-Owned: No
Listed since: 05-20-2025 - $39,998fair price$341 above market
- 30,704 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- CarMax (In-stock online)
- Transfer available from KY to VA*
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Located in Louisville, KY / 522 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: 5TDKDRBH7PS036649
Stock: 26845944
Certified Pre-Owned: No - New Listing$31,990good price$1,174 below market
- 43,702 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Philadelphia, PA / 236 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: 5TDKDRAH8PS022888
Stock: 2003692690
Certified Pre-Owned: No
Listed since: 05-02-2025 - $31,777good price$1,163 below market
- 99,625 miles
- No accidents, 2 owners, corporate fleet vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Koons of Woodbridge (142 mi away)
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Located in Woodbridge, VA / 142 miles away from Chesapeake, VA
Visit Koons Automotive of Woodbridge online at www.koonsofwoodbridge.com to see more pictures of this vehicle or call us at 571-285-3277 today to sch...
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: 5TDJZRBH3MS097084
Stock: 36516
Certified Pre-Owned: No - $27,861good price
- 95,115 miles
- No accidents, 1 owner, corporate fleet vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Dallas, TX / 1,189 miles away from Chesapeake, VA
3rd Row Seat,Apple CarPlay,Back-Up Camera,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Satellite Radio,Turbo/Supercharged,WiFi Hotspot,3rd...
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: 5TDKDRAH4PS501034
Stock: PS501034P
Certified Pre-Owned: No - New Listing
- 2,141 miles
- No accidents, 1 owner, personal use
- 8 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from WA to VA*
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Located in Spokane Valley, WA / 2,203 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: 5TDKDRAH0PS036140
Stock: 27194814
Certified Pre-Owned: No - Price Drop$29,600good price$1,544 below market
- 52,580 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Lindsay Ford of Wheaton (165 mi away)
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Located in Wheaton, MD / 165 miles away from Chesapeake, VA
CARFAX One-Owner. Clean CARFAX. Priced below KBB Fair Purchase Price! 22/29 City/Highway MPG DONT DELAY! CALL NOW OR JUST COME ON IN! YOU WONT WANT TO...
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: 5TDKDRAH9PS500221
Stock: FP10534
Certified Pre-Owned: No
Listed since: 05-23-2025 - Price Drop$32,525fair price$789 below market
- 72,010 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Bayside Toyota (128 mi away)
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Located in Prince Frederick, MD / 128 miles away from Chesapeake, VA
One Owner 2023 Toyota Highlander XLE...Need space for the family, friends, gear, and maybe a few snacks you swore you’d stop eating? The 2023 Toyota 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH5PS026140
Stock: PS026140A
Certified Pre-Owned: No
Listed since: 05-09-2025 - $35,998fair price$381 above market
- 10,541 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CO to VA*
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Located in Loveland, CO / 1,567 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: 5TDKDRAH9PS504477
Stock: 27193211
Certified Pre-Owned: No - $32,939good price$1,419 below market
- 21,079 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Fresno, CA / 2,387 miles away from Chesapeake, VA
CarFax 1-Owner,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Remote Start,Sate...
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: 5TDKDRAH0PS029978
Stock: PS029978PR
Certified Pre-Owned: No - Price Drop$38,427fair price$758 below market
- 45,892 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 28 Hwy MPG
- Alfa Romeo of Raleigh (144 mi away)
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Located in Raleigh, NC / 144 miles away from Chesapeake, VA
Clean CARFAX. CARFAX One-Owner. 2023 Toyota Highlander XLE 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hpAWD.WHO WE ARE Masera...
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: 5TDKDRBHXPS044325
Stock: EP69792
Certified Pre-Owned: No
Listed since: 05-03-2025 - $36,998fair price$131 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 - $28,998fair price$414 below market
- 89,969 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax Fayetteville (191 mi away)
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Located in Fayetteville, NC / 191 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/29 Highway)
Listing Information:
VIN: 5TDGZRAH1MS533295
Stock: 26982663
Certified Pre-Owned: No - $40,998fair price$276 below market
- 12,877 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 Irvine, CA / 2,335 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: 5TDKDRAHXPS041300
Stock: 27452941
Certified Pre-Owned: No - $41,998fair price$267 above market
- 38,462 miles
- No accidents, 1 owner, personal use
- 7 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to VA*
Close
Located in Norco, CA / 2,320 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: 5TDKDRAH3PS039100
Stock: 27270886
Certified Pre-Owned: No
Showing 274 - 294 out of 2,162 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 L 4dr SUV (2.4L 4cyl Turbo 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $26,254 | $27,768 | $29,473 |
| Clean | $25,925 | $27,390 | $29,042 |
| Average | $25,377 | $26,762 | $28,323 |
| Rough | $24,664 | $25,945 | $27,389 |
The average list price of a used 2023 Toyota Highlander in Chesapeake, Virginia is $35,275. The average mileage on a used Toyota Highlander 2023 for sale in Chesapeake, Virginia is 43,831. Based on the average mileage of 43,831 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 $25,377.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.