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2,076 listings
- New Listing
- 17,904 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Dulles (171 mi away)
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Located in Sterling, VA / 171 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: 5TDFZRBH8MS087687
Stock: 27276051
Certified Pre-Owned: No - $37,917fair price$377 above market
- 61,424 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Sanford Imports (187 mi away)
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Located in Sandford, NC / 187 miles away from Chesapeake, VA
Recent Arrival! Priced below KBB Fair Purchase Price!2021 Toyota Highlander Platinum Midnight Black Metallic Carfax Accident Free, Leather Seats, Nav...
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: 5TDFZRBH2MS085191
Stock: 7006017
Certified Pre-Owned: No
Listed since: 05-22-2025 - Price Drop
- 93,532 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 19 City / 26 Hwy MPG
- Chesapeake DriveTime (4 mi away)
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Located in Chesapeake, VA / 4 miles away from Chesapeake, VA
Shop at DriveTime: Get started on your personalized car-buying journey today. With no credit impact, you can get approved for your real, personalized ...
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:
22 Combined MPG (19 City/26 Highway)
Listing Information:
VIN: 5TDBZRFH7KS997501
Stock: 1630090954
Certified Pre-Owned: No
Listed since: 04-30-2025 - New Listing$33,356fair price$441 below 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 - Price Drop$35,795fair price$724 above market
- 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 - $31,995fair price$11 above market
- 77,712 miles
- 1 accident, 1 owner, corporate fleet vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Imperial Highline (157 mi away)
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Located in Manassas, VA / 157 miles away from Chesapeake, VA
LOADED WITH VALUE! Comes equipped with: Cockpit Red, Leather Seat Trim. This Toyota Highlander also includes Power Driver's Seat, Clock, Climate Contr...
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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDLZRAH9MS051737
Stock: 51737
Certified Pre-Owned: No
Listed since: 04-29-2025 - New Listing$31,998fair price$243 above market
- 59,550 miles
- 7 Seats, 20 City / 26 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 Unavailable.
Features and Specs:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDDZRFH7KS963423
Stock: 27446517
Certified Pre-Owned: No - New Listing$32,998fair price$205 above market
- 60,336 miles
- 7 Seats, 20 City / 26 Hwy MPG
- CarMax Ellicott City (179 mi away)
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Located in Ellicott City, MD / 179 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDDZRFH2KS722210
Stock: 27096769
Certified Pre-Owned: No - $34,860fair price$174 above market
- 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 - 103,651 miles
- Frame damage reported, 2 owners, personal use only
- 7 Seats, 21 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: 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:
23 Combined MPG (21 City/27 Highway)
Listing Information:
VIN: 5TDKZRFH2KS554270
Stock: KMM13092
Certified Pre-Owned: No- 28,808 miles
- 2 accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Lucky Line Motors (127 mi away)
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Located in Fredericksburg, VA / 127 miles away from Chesapeake, VA
***** WE FINANCE ***** 2021 TOYOTA HIGHLANDER LE ONE OWNER CARFAX / VEHICLE LOADED WITH PREMIUM SOUND SYSTEM / AUX PORT / BLUETOOTH CONNECTION/ BACKUP...
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: 5TDBZRBHXMS153767
Stock: LLM11887
Certified Pre-Owned: No- New Listing
- 32,528 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Carvana - Richmond (100 mi away)
- Home delivery*
Close
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: 5TDHZRBH6MS061453
Stock: 2003705610
Certified Pre-Owned: No
Listed since: 05-10-2025 - 124,375 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 26 Hwy MPG
- Koons of Woodbridge (142 mi away)
Close
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: 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH7KS741726
Stock: 37108
Certified Pre-Owned: No- Price Drop
- 38,098 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 26 Hwy MPG
- Carvana - Richmond (100 mi away)
- Home delivery*
Close
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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH6KS598509
Stock: 2003713430
Certified Pre-Owned: No
Listed since: 05-20-2025 - 30,352 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 26 Hwy MPG
- CarMax Charlottesville (151 mi away)
Close
Located in Charlottesville, VA / 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: 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH0KS626238
Stock: 27239372
Certified Pre-Owned: No- 108,267 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Trent Buick GMC (123 mi away)
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Located in New Bern, NC / 123 miles away from Chesapeake, VA
CARFAX One-Owner. White 2021 Toyota Highlander Platinum AWD 8-Speed Automatic 3.5L V6 DOHC Highlander Platinum, 4D Sport Utility, 3.5L V6 DOHC, 8-Spee...
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: 5TDFZRBH7MS074235
Stock: B53369C
Certified Pre-Owned: No
Listed since: 04-28-2025- 37,452 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- New Listing
- 84,686 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Carvana - Richmond (100 mi away)
- Home delivery*
Close
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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDDZRFH5KS926130
Stock: 2003764989
Certified Pre-Owned: No
Listed since: 05-23-2025 - 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*
Close
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)
Close
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 - New Listing
- 57,012 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 26 Hwy MPG
- Heritage Toyota Owings Mills (187 mi away)
Close
Located in Owings Mills, MD / 187 miles away from Chesapeake, VA
Recent Arrival! **ALL WHEEL DRIVE**, **POWER DRIVERS SEAT**, **HEATED LEATHER SEATS**, **POWER SUNROOF**, **NAVIGATION SYSTEM**, **BACKUP CAMERA**, **...
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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFH5KS564738
Stock: 7P564738
Certified Pre-Owned: No
Listed since: 05-26-2025
Showing 85 - 105 out of 2,076 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
"Some Adjustment Needed"
Bill, 01/11/2020
2020 Toyota Highlander Limited 4dr SUV (3.5L 6cyl 8A)
Test drove the 2020 Limited. V-6 engine was responsive and ride was very quiet. Very good standard technology and driving safety packages. Interior had quality materials and good fit and finish. Second row captains chair seats are comfortable with plenty of room behind first row, third row seats useless except for small children which you would want in second row. Big disappointment … was drivers seat height adjustment; you better be 5'4" or above to have clear visibility over steering wheel and dash. Also, passenger seat has NO height adjustment; passengers 6'3" or above will be at or close to the ceiling. Except for the lack of adequate front seat height adjustments, I loved the car.
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 | $32,099 | $34,260 | $36,427 |
| Clean | $31,416 | $33,514 | $35,615 |
| Average | $30,277 | $32,269 | $34,261 |
| Rough | $28,796 | $30,652 | $32,502 |
The average list price of a used 2021 Toyota Highlander in Chesapeake, Virginia is $33,482. The average mileage on a used Toyota Highlander 2021 for sale in Chesapeake, Virginia is 61,999. Based on the average mileage of 61,999 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 $30,277.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.