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1,859 listings
- New Listing
- 38,607 miles
- 7 Seats, 20 City / 27 Hwy MPG
- Hall Toyota Virginia Beach (14 mi away)
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Located in Virginia Beach, VA / 14 miles away from Chesapeake, VA
Silver 2021 Toyota Highlander Platinum AWD 8-Speed Automatic 3.5L V6 DOHC AWD.AWD, 11 Speakers, 20" Painted Alloy Wheels, 3.003 Axle Ratio, 3rd row ...
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDFZRBH0MS100478
Stock: 24255595A
Certified Pre-Owned: No
Listed since: 05-31-2025 - New Listing
- 19,296 miles
- 1 accident, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Raleigh (151 mi away)
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Located in Raleigh, NC / 151 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 - New Listing
- 70,656 miles
- No accidents, 1 owner, taxi vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Safford Brown Manassas Hyundai (156 mi away)
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Located in Manassas, VA / 156 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
- 78,352 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Global Auto Outlet (150 mi away)
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Located in Temple Hills, MD / 150 miles away from Chesapeake, VA
Estimated monthly payment and estimated total purchase price include the Maryland processing fee of $800 (not required by law). Taxes and additional f...
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: 5TDLZRBH8MS102885
Stock: 102885
Certified Pre-Owned: No
Listed since: 05-29-2025 - New Listing
- 65,728 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Global Auto Outlet (150 mi away)
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Located in Temple Hills, MD / 150 miles away from Chesapeake, VA
Estimated monthly payment and estimated total purchase price include the Maryland processing fee of $800 (not required by law). Taxes and additional f...
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: 5TDJZRBH3MS142587
Stock: 142587
Certified Pre-Owned: No
Listed since: 05-29-2025 - New Listing
- 92,032 miles
- No accidents, 2 owners, corporate fleet vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- Kargar Motors (156 mi away)
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Located in Manassas, VA / 156 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 - New Listing
- 38,546 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- i.g. Burton Toyota of Dover (174 mi away)
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Located in Dover, DE / 174 miles away from Chesapeake, VA
TOYOTA CERTIFIED, ONE OWNER, CLEAN CARFAX, NAVIGATION, CAR PLAY, HEATED & COOLED LEATHER SEATS, POWER LIFTGATE, SUNROOF, JBL PREMIUM STEREO, BLIND SPO...
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: 5TDDZRBH6MS536503
Stock: TP25112
Certified Pre-Owned: Yes
Listed since: 05-27-2025 - 38,637 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Danville Toyota (178 mi away)
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Located in Danville, VA / 178 miles away from Chesapeake, VA
Toyota Gold Certified Details: * Warranty Deductible: $0 * Roadside Assistance for 7 Year / 100,000 Mile. Standard New-Car Financing Rates Availa...
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: 5TDKDRAH1PS503100
Stock: P6633
Certified Pre-Owned: Yes
Listed since: 05-05-2025- 39,036 miles
- No accidents, 1 owner, personal use
- 8 Seats, 21 City / 28 Hwy MPG
- Battlefield Toyota (155 mi away)
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Located in Culpeper, VA / 155 miles away from Chesapeake, VA
++1-OWNER++ XLE PACKAGE++ LEATHER++ SECOND ROW BENCH SEAT++ AWD++ 2023 Toyota Highlander XLE 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp 21/2...
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: 5TDKDRBH9PS013955
Stock: P5503
Certified Pre-Owned: No
Listed since: 05-27-2025- 54,161 miles
- Frame damage reported, 2 owners, corporate fleet vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- Kargar Motors (156 mi away)
Close
Located in Manassas, VA / 156 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- New ListingNot Priced
- 21,107 miles
- 7 Seats, 22 City / 29 Hwy MPG
- 355 Toyota (172 mi away)
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Located in Rockville, MD / 172 miles away from Chesapeake, VA
2023 Toyota Highlander XLE Recent Arrival! Clean CARFAX.Magnetic Gray Metallic FWD 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp 8-Speed Au...
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH3PS513241
Stock: 52J2052A
Certified Pre-Owned: No
Listed since: 05-31-2025 - Price Drop
- 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 ListingNot Priced
- 21,874 miles
- 7 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 Platinum Blue AWD AutomaticAWD.Introducing our PASSPORT ONE PRICE program where qualified pre-owned vehicl...
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH4PS528023
Stock: 28582A
Certified Pre-Owned: No
Listed since: 05-31-2025 - 83,863 miles
- Frame damage reported, 1 owner, corporate fleet vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- CarHub (138 mi away)
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Located in Stafford, VA / 138 miles away from Chesapeake, VA
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: 5TDGZRBH9MS107983
Stock: 107983
Certified Pre-Owned: No- Price Drop$25,400great price$3,322 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)
Close
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 - Price Drop$40,500great price$4,364 below market
- 21,415 miles
- 1 accident, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Ourisman Toyota of Woodbridge (144 mi away)
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Located in Woodbridge, VA / 144 miles away from Chesapeake, VA
ABS brakes, Active Cruise Control, Alloy wheels, Electronic Stability Control, Front dual zone A/C, Heated door mirrors, Heated Front Bucket Seats, He...
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: 5TDKDRAH3RS541110
Stock: A541110
Certified Pre-Owned: Yes
Listed since: 05-03-2025 - Price Drop
- 82,203 miles
- Frame damage reported, 1 owner, personal use only
- 8 Seats, 21 City / 29 Hwy MPG
- Xride Cars (148 mi away)
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Located in Raleigh, NC / 148 miles away from Chesapeake, VA
We are excited to offer this 2021 Toyota Highlander L Sport Utility 4D, now available at Xride Cars, located at 1733 Capital Blvd, Raleigh, NC 27604. ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDCZRAH1MS041672
Stock: 041672
Certified Pre-Owned: No - New Listing
- 49,839 miles
- Frame damage reported, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Royal Auto Club (169 mi away)
Close
Located in Sterling, VA / 169 miles away from Chesapeake, VA
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAHXPS042351
Stock: SAI3070
Certified Pre-Owned: No
Showing 190 - 210 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 2021 Toyota Highlander in Chesapeake, VA Values
Estimated values
2021 Toyota Highlander Platinum 4dr SUV AWD (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $35,409 | $37,685 | $39,968 |
| Clean | $34,655 | $36,864 | $39,077 |
| Average | $33,399 | $35,495 | $37,592 |
| Rough | $31,766 | $33,716 | $35,661 |
The average list price of a used 2021 Toyota Highlander in Chesapeake, Virginia is $35,386. The average mileage on a used Toyota Highlander 2021 for sale in Chesapeake, Virginia is 52,679. Based on the average mileage of 52,679 for used 2021 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 2021 in Chesapeake, Virginia to be $33,399.
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