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2,134 listings
- Price Drop
- 55,674 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 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: 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: 5TDFZRBH5MS063122
Stock: 2003720911
Certified Pre-Owned: No
Listed since: 05-15-2025 - New Listing
- 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 wonderful 2021 Toyota Highlander Celestial Silver Metallic XLE with the follow...
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
- 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 - 54,775 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Harrisonburg (187 mi away)
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Located in Harrisonburg, VA / 187 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: 5TDLZRBH7MS064212
Stock: 26948363
Certified Pre-Owned: No- 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$131 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 - 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 - Price Drop$38,495great price$4,106 below market
- 21,583 miles
- No accidents, 3 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Vineland Hyundai (197 mi away)
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Located in Millville, NJ / 197 miles away from Chesapeake, VA
REMAINDER OF FACTORY WARRANTY, MOONROOF, LOCAL TRADE, CLEAN CAR FAX, BLIND SPOT MONITORING SYSTEM, BACK-UP CAMERA, APPLE CAR PLAY, ANDROID AUTO, ALL W...
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: 5TDLZRBH4NS240912
Stock: V00915A
Certified Pre-Owned: No
Listed since: 03-29-2025 - Price Drop$25,800great price$2,771 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 - 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 - 54,161 miles
- Frame damage reported, 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
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- Price Drop$35,500great price$3,768 below market
- 23,477 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Safford Brown Manassas Hyundai (156 mi away)
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Located in Manassas, VA / 156 miles away from Chesapeake, VA
Celestial Silver Metallic 2022 Toyota Highlander XLE AWD 8-Speed Automatic 3.5L V6 DOHC Third Row Seating, Blind Spot Monitoring, Navigation System, A...
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: 5TDHZRBH4NS226322
Stock: H046813A
Certified Pre-Owned: No
Listed since: 03-24-2025 - 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- 65,521 miles
- 1 accident, 1 owner, 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: 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDLZRBHXMS056802
Stock: 36908
Certified Pre-Owned: No- Price Drop$25,400great price$3,345 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 - 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$37,500great price$3,167 below market
- 17,502 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Ourisman Chevrolet of Rockville (168 mi away)
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Located in Rockville, MD / 168 miles away from Chesapeake, VA
CARFAX One-Owner. This 2022 Midnight Black Toyota Highlander XSE AWD is well equipped and includes these features and benefits:.20/27 City/Highway MPG...
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: 5TDLZRBH5NS222239
Stock: B5052
Certified Pre-Owned: No
Listed since: 04-01-2025 - 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 - Price Drop$32,500great price$3,679 below market
- 66,827 miles
- No accidents, 1 owner, corporate fleet vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Hanna Imports (148 mi away)
Close
Located in Raleigh, NC / 148 miles away from Chesapeake, VA
*Carfax Accident Free*, *Multi Point Inspection*, AWD, 3rd row seats: split-bench, Alloy wheels, Apple CarPlay/Android Auto, Automatic temperature con...
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: 5TDGZRBH0NS577868
Stock: 3021149
Certified Pre-Owned: No
Listed since: 03-04-2025
Showing 43 - 63 out of 2,134 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
Couldn’t be happier!
S Curry, 01/02/2021
2021 Toyota Highlander Limited 4dr SUV AWD (3.5L 6cyl 8A)
I’ve been eyeing the Highlander since they redesigned it in 2020. I opted for the Limited AWD trim with the optional 12 inch screen and bench seats. I am completely blown away on how amazing it is to drive the Highlander. Visibility is great but with the bigger screen you also get birds eye view which will definitely help assess your surroundings. The safety features are awesome and the … little things like intuitive climate control are nice. I was worried about access into the third row and comfort but my 12 year old is happy with it. The middle row does slide up giving more leg room to the third row. I came from a minivan so I am used to a lot of cargo room and low entry. If you will be using the third row consistently I recommend getting the cross bars and on roof cargo storage to maximize what you can carry, and if you are transporting smaller kids/adults the step up may be just slightly too high for them but running boards can be installed.
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 | $33,215 | $35,494 | $37,779 |
| Clean | $32,508 | $34,720 | $36,936 |
| Average | $31,330 | $33,431 | $35,533 |
| Rough | $29,798 | $31,755 | $33,708 |
The average list price of a used 2021 Toyota Highlander in Chesapeake, Virginia is $33,648. The average mileage on a used Toyota Highlander 2021 for sale in Chesapeake, Virginia is 58,641. Based on the average mileage of 58,641 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 $31,330.
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