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1,859 listings
- 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 9405 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 16553 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- Price Drop
- 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- 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- 103,073 miles
- 1 accident, 2 owners, personal use only
- 8 Seats, 21 City / 29 Hwy MPG
- Sir Walter Chevrolet (151 mi away)
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Located in Raleigh, NC / 151 miles away from Chesapeake, VA
**2021 Toyota Highlander LE** For Sale at **Sir Walter Chevrolet** âś… 8-Speed Automatic Transmission âś… 3.5L V6 Engine âś… Toyota Safety Sense 2.5...
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: 5TDZZRAH2MS518636
Stock: 255102B
Certified Pre-Owned: No
Listed since: 04-24-2025- 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- 36,524 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Jacksonville NC (149 mi away)
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Located in Jacksonville, NC / 149 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: 5TDGZRBH6MS141802
Stock: 27019321
Certified Pre-Owned: No- Price Drop
- 93,581 miles
- No accidents, 3 owners, rental vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Capital Subaru of Greenville (104 mi away)
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Located in Winterville, NC / 104 miles away from Chesapeake, VA
Recent Arrival! Capital Subaru of Greenville is delighted to offer this handsome 2021 Toyota Highlander Celestial Silver Metallic XLE with the followi...
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: 5TDGZRBH1MS087339
Stock: SAT4160A
Certified Pre-Owned: No
Listed since: 05-20-2025 - Price Drop$25,800great price$3,191 below market
- 50,802 miles
- No accidents, 3 owners, corporate fleet vehicle
- 8 Seats, 21 City / 29 Hwy MPG
- Koons Arlington Toyota (157 mi away)
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Located in Arlington, VA / 157 miles away from Chesapeake, VA
2020 Toyota Highlander LE 3rd row seats: split-bench, Apple CarPlay/Android Auto, Auto High-beam Headlights, Automatic temperature control, Exterior P...
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: 5TDZZRAH6LS508707
Stock: A10685
Certified Pre-Owned: No
Listed since: 04-18-2025 - 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 - Price Drop
- 99,071 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 CARFAX One-Owner. Clean CARFAX.Highlander XLE, 4D Sport Utility, 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp, 8-...
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 - 72,678 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Crossroads Ford of Dunn-Benson (166 mi away)
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Located in Dunn, NC / 166 miles away from Chesapeake, VA
1 Owner, AWD, 3rd row seats: split-bench, 6 Speakers, AM/FM radio: SiriusXM, Apple CarPlay/Android Auto, Automatic temperature control, Exterior Parki...
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: 5TDLZRBHXMS082686
Stock: U649A
Certified Pre-Owned: No
Listed since: 05-10-2025- 72,375 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
- 44,101 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Charles Boyd Chevrolet GMC (126 mi away)
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Located in Henderson, NC / 126 miles away from Chesapeake, VA
Thank You for shopping at Charles Boyd Chevrolet Cadillac GMC! AWD. White 2021 Toyota Highlander XLE Odometer is 12551 miles below market average! AWD...
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: 5TDGZRBH7MS133501
Stock: 117-25B
Certified Pre-Owned: No
Listed since: 03-27-2025 - New Listing$33,356fair price$336 above market
- 84,599 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Beyer Kia Falls Church (158 mi away)
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Located in Falls Church, VA / 158 miles away from Chesapeake, VA
AWD.Red 2021 Toyota Highlander LimitedAWD 8-Speed Automatic 3.5L V6 DOHC Recent Arrival! 20/27 City/Highway MPG
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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDDZRBH1MS526607
Stock: E10748VK
Certified Pre-Owned: No
Listed since: 05-27-2025 - New Listing
- 18,533 miles
- 1 accident, 1 owner, personal use only
- 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
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: 5TDKDRBH5PS042840
Stock: 27450482
Certified Pre-Owned: No - New Listing$33,991fair price$314 above market
- 75,253 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Battlefield Toyota (155 mi away)
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Located in Culpeper, VA / 155 miles away from Chesapeake, VA
++1-OWNER++ LIMITED PACKAGE++AWD++ 2021 Toyota Highlander Limited 3.5L V6 DOHC 20/27 City/Highway MPG
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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDDZRBH5MS526657
Stock: T18858A
Certified Pre-Owned: No
Listed since: 05-30-2025 - 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
Showing 169 - 189 out of 1,859 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
Rolling again
Ken S, 10/28/2021
2022 Toyota Highlander Limited 4dr SUV AWD (3.5L 6cyl 8A)
Just replaced a 2018 Highlander due to accident. Of course the car is comfortable and nice to drive but I especially appreciate it after the accident. The 2018 was totaled because of a head on collision. My wife and I only had minor injuries that I attribute to the strength of the vehicle and the air bags that completely isolated us.
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 | $24,245 | $25,714 | $27,371 |
| Clean | $23,941 | $25,365 | $26,971 |
| Average | $23,435 | $24,783 | $26,303 |
| Rough | $22,777 | $24,026 | $25,436 |
The average list price of a used 2023 Toyota Highlander in Chesapeake, Virginia is $35,870. The average mileage on a used Toyota Highlander 2023 for sale in Chesapeake, Virginia is 53,826. Based on the average mileage of 53,826 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 $23,435.
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