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2,076 listings
- New Listing$42,495fair price$481 above market
- 24,671 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Trust Auto (193 mi away)
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Located in Sykesville, MD / 193 miles away from Chesapeake, VA
Trust Auto is pleased to be currently offering this Loaded 2023 Toyota Highlander XSE AWD 7-Passanger SUV with 24,671mi. This Toyota includes: 50 STAT...
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/28 Highway)
Listing Information:
VIN: 5TDKDRBH7PS001044
Stock: 001044
Certified Pre-Owned: No
Listed since: 05-09-2025 - Price Drop$33,921fair price$52 above market
- 38,259 miles
- No accidents, 2 owners, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Passport Toyota (150 mi away)
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Located in Suitland, MD / 150 miles away from Chesapeake, VA
Recent Arrival! 2023 Toyota Highlander LE Magnetic Gray Metallic AWD AutomaticBlind Spot Monitor, Backup Camera, Bluetooth, USB Ports, AUX Input, 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:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH7PS040300
Stock: B8803
Certified Pre-Owned: No
Listed since: 05-21-2025 - 49,116 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- DARCARS Toyota of Silver Spring (166 mi away)
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Located in Silver Spring, MD / 166 miles away from Chesapeake, VA
2023 Toyota Highlander L CARFAX One-Owner.Cypress FWD 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp 8-Speed Automatic 22/29 City/Highway MPG
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: 5TDKDRAH8PS500789
Stock: E1A0507
Certified Pre-Owned: No
Listed since: 04-25-2025- $37,498fair price$57 above market
- 51,540 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Toyota of Goldsboro (134 mi away)
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Located in Goldsboro, NC / 134 miles away from Chesapeake, VA
CARFAX One-Owner. Moon Dust 2023 Toyota Highlander XLE FWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp Toyota Certified, An...
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: 5TDKDRAH4PS020202
Stock: P3759
Certified Pre-Owned: Yes
Listed since: 05-13-2025 - 26,000 miles
- No accidents, 1 owner, personal use
- 8 Seats, 22 City / 29 Hwy MPG
- Marine Chevrolet (149 mi away)
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Located in Jacksonville, NC / 149 miles away from Chesapeake, VA
CARFAX One-Owner. Clean CARFAX. Certified. Midnight Black Metallic 2023 Toyota Highlander L FWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LE...
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: 5TDKDRAH0PS518784
Stock: ST1988AT
Certified Pre-Owned: No
Listed since: 05-13-2025- 28,048 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 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: No
Features and Specs:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH5PS027465
Stock: 27122921
Certified Pre-Owned: No- New Listing
- 43,550 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- AutoNation Chevrolet Laurel (167 mi away)
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Located in Laurel, MD / 167 miles away from Chesapeake, VA
Sun/Moonroof3rd Row SeatAll Weather Floor & Cargo Liner (Tms)Lane Keeping AssistKeyless StartRear Spoiler50 State EmissionsBlack; Softex Seat 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: 5TDKDRAH0PS020018
Stock: PS020018
Certified Pre-Owned: No
Listed since: 05-28-2025 - 36,803 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- The Car Store (121 mi away)
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Located in Salisbury, MD / 121 miles away from Chesapeake, VA
NO ACCIDENTS, ONE OWNER, Highlander L, 4D Sport Utility, 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp, 8-Speed Automatic, FWD, Celestial Silve...
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: 5TDKDRAH0PS033688
Stock: 61647
Certified Pre-Owned: No
Listed since: 02-11-2025- 48,416 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Exclusive Motor Cars (186 mi away)
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Located in Randallstown, MD / 186 miles away from Chesapeake, VA
CARFAX One-Owner. This 2023 Gray Toyota Highlander L FWD is well equipped and includes these features and benefits:. FWD Clean CARFAX. 22/29 City/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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH7PS020369
Stock: S020369
Certified Pre-Owned: No
Listed since: 05-07-2025- Price Drop
- 39,258 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Passport Toyota (150 mi away)
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Located in Suitland, MD / 150 miles away from Chesapeake, VA
Recent Arrival! 2023 Toyota Highlander LE Wind Chill Pearl AWD AutomaticBlind Spot Monitor, Backup Camera, Bluetooth, USB Ports, AUX Input, Toyota S...
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: 5TDKDRBH1PS033309
Stock: B8802
Certified Pre-Owned: No
Listed since: 05-21-2025 - 99,062 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- DARCARS Toyota of Baltimore (177 mi away)
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Located in Baltimore, MD / 177 miles away from Chesapeake, VA
2023 Toyota Highlander XLE Recent Arrival! CARFAX One-Owner. Clean CARFAX.Highlander XLE, 4D Sport Utility, 2.4L I4 PDI Turbocharged DOHC 16V LEV3-S...
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: 5TDKDRAH3PS516107
Stock: 51E2141A
Certified Pre-Owned: No
Listed since: 05-15-2025- Price Drop$41,590great price$5,790 below market
- 22,059 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 28 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:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH4RS536920
Stock: 2003531142
Certified Pre-Owned: No
Listed since: 03-11-2025 - Price Drop
- 72,364 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- John Hiester Chrysler Dodge Jeep Ram of Sanford (185 mi away)
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Located in Sanford, NC / 185 miles away from Chesapeake, VA
CLEAN CARFAX, ONE OWNER, FAST AND EASY FINANCING, THE NEW PRICE OUTLET, ABS brakes, Active Cruise Control, Alloy wheels, Electronic Stability Control,...
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: 5TDKDRAHXPS031477
Stock: S3297
Certified Pre-Owned: No
Listed since: 05-13-2025 - New Listing
- 16,876 miles
- 8 Seats, 22 City / 29 Hwy MPG
- CarMax Fredericksburg (126 mi away)
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Located in Fredericksburg, VA / 126 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 Unavailable.
Features and Specs:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH4PS025903
Stock: 27273965
Certified Pre-Owned: No - New Listing
- 18,533 miles
- 7 Seats, 21 City / 28 Hwy MPG
- CarMax White Marsh (182 mi away)
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Located in White Marsh, MD / 182 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 Unavailable.
Features and Specs:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH5PS042840
Stock: 27450482
Certified Pre-Owned: No - Not Priced
- 72,000 miles
- No accidents, 1 owner, personal use
- 7 Seats, 22 City / 29 Hwy MPG
- Royal Auto Club (169 mi away)
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Located in Sterling, VA / 169 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: 5TDKDRAH1PS035837
Stock: SAI2964
Certified Pre-Owned: No 
Photos not available- 23,820 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Toyota of Goldsboro (134 mi away)
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Located in Goldsboro, NC / 134 miles away from Chesapeake, VA
CARFAX One-Owner. Odometer is 9427 miles below market average! Pear 2023 Toyota Highlander L FWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V L...
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: 5TDKDRAH9PS031938
Stock: P3756
Certified Pre-Owned: Yes
Listed since: 05-13-2025- 24,409 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Toyota of Goldsboro (134 mi away)
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Located in Goldsboro, NC / 134 miles away from Chesapeake, VA
CARFAX One-Owner. Odometer is 15503 miles below market average! Ruby 2023 Toyota Highlander XSE FWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16...
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: 5TDKDRAHXPS026392
Stock: P3748
Certified Pre-Owned: Yes
Listed since: 05-13-2025- 45,667 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 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: 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: 5TDKDRAH7PS018380
Stock: J6820
Certified Pre-Owned: No
Listed since: 05-08-2025- 45,716 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 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: 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: 5TDKDRAH0PS010542
Stock: J6882
Certified Pre-Owned: No
Listed since: 05-22-2025- New ListingPhotos not available
- 37,773 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Battlefield Toyota (155 mi away)
Close
Located in Culpeper, VA / 155 miles away from Chesapeake, VA
AWD.2023 Toyota Highlander LE 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp 21/28 City/Highway MPG
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: 5TDKDRBHXPS034040
Stock: P5502
Certified Pre-Owned: No
Listed since: 05-27-2025
Showing 64 - 84 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 2023 Toyota Highlander in Chesapeake, VA Values
Estimated values
2023 Toyota Highlander XSE 4dr SUV AWD (2.4L 4cyl Turbo 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $32,933 | $34,939 | $37,200 |
| Clean | $32,520 | $34,464 | $36,655 |
| Average | $31,833 | $33,673 | $35,749 |
| Rough | $30,939 | $32,645 | $34,570 |
The average list price of a used 2023 Toyota Highlander in Chesapeake, Virginia is $38,049. The average mileage on a used Toyota Highlander 2023 for sale in Chesapeake, Virginia is 41,140. Based on the average mileage of 41,140 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 $31,833.
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