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2,139 listings
- 39,258 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Passport Toyota (149 mi away)
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Located in Suitland, MD / 149 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- Price Drop
- 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$41,590great price$5,512 below market
- 22,059 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 28 Hwy MPG
- Carvana - Richmond (99 mi away)
- Home delivery*
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Located in Richmond, VA / 99 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 - 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 - 87,969 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Reidsville Nissan (194 mi away)
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Located in Reidsville, NC / 194 miles away from Chesapeake, VA
CARFAX One-Owner. Blue 2021 Toyota Highlander XLE AWD 8-Speed Automatic 3.5L V6 DOHC Fully Detailed, AWD.20/27 City/Highway MPGAwards: * ALG Res...
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: 5TDHZRBH6MS064689
Stock: R13396
Certified Pre-Owned: No
Listed since: 05-13-2025- 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 - New Listing
- 19,296 miles
- 1 accident, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Raleigh (152 mi away)
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Located in Raleigh, NC / 152 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH1MS558714
Stock: 27170703
Certified Pre-Owned: No - 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- Not Priced
- 75,800 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 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: 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: 5TDGZRAH2MS516196
Stock: SAI2966
Certified Pre-Owned: No - 52,956 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: 5TDKDRAH4PS502376
Stock: J6880
Certified Pre-Owned: No
Listed since: 05-22-2025- New Listing
- 70,656 miles
- No accidents, 1 owner, taxi vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Safford Brown Manassas Hyundai (155 mi away)
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Located in Manassas, VA / 155 miles away from Chesapeake, VA
Recent Arrival! Midnight Black 2023 Toyota Highlander XLE AWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp21/28 City/Highwa...
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: 5TDKDRBH3PS035756
Stock: U901055A
Certified Pre-Owned: No
Listed since: 05-29-2025 - New Listing$34,998great price$5,062 below market
- 33,747 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- CarMax Frederick (173 mi away)
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Located in Gaithersburg, MD / 173 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:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH5RS553578
Stock: 27363833
Certified Pre-Owned: No - New Listing
- 92,032 miles
- No accidents, 2 owners, corporate fleet vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- Kargar Motors (155 mi away)
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Located in Manassas, VA / 155 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH6MS059455
Stock: KMM8582
Certified Pre-Owned: No - 54,161 miles
- Frame damage reported, 2 owners, corporate fleet vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- Kargar Motors (155 mi away)
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Located in Manassas, VA / 155 miles away from Chesapeake, VA
BUYING A CAR HAS NEVER BEEN THIS EASY.We specialize in 100% GUARANTEED APPROVAL. BAD CREDIT, NO CREDIT, BANKRUPTCY, REPO, FORECLOSURE...NO PROBLEM. NO...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: No
History Provider: AutoCheck
Title Details: Issue reported
Salvage Vehicle: No
Frame Damage: Yes
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDBZRBH0MS099993
Stock: KMM12668
Certified Pre-Owned: No- 43,983 miles
- 2 accidents, 2 owners, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Auction Direct USA (151 mi away)
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Located in Raleigh, NC / 151 miles away from Chesapeake, VA
CARFAX One-Owner. Auction Direct is proud to present you with another True Market Priced Pre-Owned Vehicle. This 2021 Toyota Highlander XLE is loaded ...
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: 5TDGZRBH8MS548634
Stock: AD01052
Certified Pre-Owned: No
Listed since: 05-09-2025- 51,451 miles
- 2 accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- M and B Auto Group (156 mi away)
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Located in Bealeton, VA / 156 miles away from Chesapeake, VA
**ONE OWNER** 2021 TOYOTA HIGHLANDER AWD with powerful 3.5L V6 DOHC -INC 24-VALVE D-4S INJECTION engine and driven 51451 miles!CARFAX CERTIFIED**FINA...
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: Yes
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH3MS548508
Stock: mda5050
Certified Pre-Owned: No- New Listing
- 54,775 miles
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Harrisonburg (186 mi away)
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Located in Harrisonburg, VA / 186 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDLZRBH7MS064212
Stock: 26948363
Certified Pre-Owned: No - New Listing$40,590great price$3,628 below market
- 26,631 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Carvana - Richmond (99 mi away)
- Home delivery*
Close
Located in Richmond, VA / 99 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: 5TDKDRAH3RS528616
Stock: 2003598548
Certified Pre-Owned: No
Listed since: 04-07-2025 - $25,400great price$3,376 below market
- 74,000 miles
- No accidents, 2 owners, rental vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Fred's Executive Auto (143 mi away)
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Located in Woodbridge, VA / 143 miles away from Chesapeake, VA
LEATHER,3RD-ROW 2 12V DC Power Outlets 2 Seatback Storage Pockets Air Filtration Bucket Folding Captain Front Facing Manual Reclining Fold Forward Sea...
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: 5TDGZRAH1LS010258
Stock: P010258
Certified Pre-Owned: No
Listed since: 12-06-2024
Showing 211 - 231 out of 2,139 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 LE 4dr SUV AWD (2.4L 4cyl Turbo 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $25,289 | $26,918 | $28,756 |
| Clean | $24,972 | $26,553 | $28,336 |
| Average | $24,444 | $25,944 | $27,635 |
| Rough | $23,758 | $25,152 | $26,723 |
The average list price of a used 2023 Toyota Highlander in Chesapeake, Virginia is $35,645. The average mileage on a used Toyota Highlander 2023 for sale in Chesapeake, Virginia is 57,365. Based on the average mileage of 57,365 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 $24,444.
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