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2,135 listings
- New Listing$27,500fair price$805 below market
- 67,640 miles
- 1 accident, 2 owners, corporate fleet vehicle
- 8 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
Recent Arrival! This 2021 Black Toyota Highlander LE AWD is well equipped and includes these features and benefits:.20/27 City/Highway MPG Bluetooth, ...
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: 5TDBZRBH1MS114453
Stock: GM5141A
Certified Pre-Owned: No
Listed since: 05-21-2025 - New Listing$39,998fair price$425 above market
- 42,719 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Midlothian (93 mi away)
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Located in Midlothian, VA / 93 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: 5TDFZRBH2MS099916
Stock: 27094145
Certified Pre-Owned: No - $37,200fair price$719 above market
- 41,538 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Lindsay Manassas Chrysler Dodge Jeep Ram (156 mi away)
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Located in Manassas, VA / 156 miles away from Chesapeake, VA
*WELL MAINTAINED*, POWER SUNROOF / SUNROOF / POWER TILT SLIDING ROOF, APPLE CARPLAY/ANDROID AUTO, BLUETOOTH, PUSH-BUTTON START, WIRELESS CHARGING, POW...
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: 5TDLZRBH8MS074151
Stock: MP8945A
Certified Pre-Owned: No
Listed since: 05-15-2025 - $37,998fair price$999 above market
- 40,361 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 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: 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: 5TDJZRBH2MS158988
Stock: 27191974
Certified Pre-Owned: No - New Listing$32,900fair price$122 below market
- 57,927 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- DARCARS Toyota of Baltimore (177 mi away)
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Located in Baltimore, MD / 177 miles away from Chesapeake, VA
2021 Toyota Highlander XLE Recent Arrival! CARFAX One-Owner.Highlander XLE, 4D Sport Utility, 3.5L V6 DOHC, 8-Speed Automatic, AWD, Blueprint, Black...
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: 5TDHZRBH3MS538596
Stock: 52E2039A
Certified Pre-Owned: No
Listed since: 05-28-2025 - Price Drop$31,251fair price$419 above market
- 65,600 miles
- No accidents, 3 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- DARCARS Honda (154 mi away)
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Located in Bowie, MD / 154 miles away from Chesapeake, VA
2021 Toyota Highlander XLE Moon Dust 8-Speed AutomaticAWD, 3rd row seats: split-bench, Apple CarPlay/Android Auto, Exterior Parking Camera Rear, Pow...
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: 5TDGZRBH1MS116306
Stock: 5P2390A
Certified Pre-Owned: No
Listed since: 05-13-2025 - $37,917fair price$195 below 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 - $31,777fair price$61 above market
- 99,625 miles
- No accidents, 2 owners, 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: 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: 5TDJZRBH3MS097084
Stock: 36516
Certified Pre-Owned: No - $18,795fair price$18 below market
- 153,237 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 21 City / 29 Hwy MPG
- Olympia Pre-Owned Auto (149 mi away)
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Located in Raleigh, NC / 149 miles away from Chesapeake, VA
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: 5TDCZRAH8MS044441
Stock: 044441
Certified Pre-Owned: No - $35,995fair price$36 above market
- 69,961 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Fitzgerald Toyota Gaithersburg (176 mi away)
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Located in Gaithersburg, MD / 176 miles away from Chesapeake, VA
Check out this great low mileage vehicle! Roomy, comfortable, and practical! This model accommodates 7 passengers comfortably, and provides features s...
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: 5TDFZRBH4MS142703
Stock: EB61729A
Certified Pre-Owned: No
Listed since: 05-06-2025 - Price Drop$31,498fair price$638 above market
- 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 - Price Drop$37,250fair price$616 above market
- 61,222 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Koons Tysons Toyota (162 mi away)
- Five Star Dealer
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Located in Vienna, VA / 162 miles away from Chesapeake, VA
AWD.RECALL NOTICE: Some vehicles offered for sale may be subject to unrepaired manufacturer safety recalls. To determine the recall status of a vehi...
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: 5TDFZRBH5MS158490
Stock: 0KW50991
Certified Pre-Owned: No
Listed since: 05-27-2025 - New Listing$39,500fair price$550 above market
- 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 - $29,888fair price$425 above market
- 90,038 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Bumble Auto - Ellicott City (179 mi away)
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Located in Ellicott City, MD / 179 miles away from Chesapeake, VA
Delve into a world of exceptional pre-owned vehicles at Bumble Auto, where quality and affordability coalesce. Our varied inventory accommodates diffe...
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: 5TDHZRBH9MS110399
Stock: B3266
Certified Pre-Owned: No - 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 - $31,995fair price$114 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 - 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- 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- 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*
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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: 5TDHZRBH6MS061453
Stock: 2003705610
Certified Pre-Owned: No
Listed since: 05-10-2025 - 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- 103,079 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** ✅ 8-Speed Automatic Transmission ✅ 3.5L V6 Engine ✅ 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
Showing 22 - 42 out of 2,135 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 LE 4dr SUV AWD (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $23,020 | $25,126 | $27,239 |
| Clean | $22,530 | $24,579 | $26,631 |
| Average | $21,713 | $23,666 | $25,619 |
| Rough | $20,651 | $22,480 | $24,303 |
The average list price of a used 2021 Toyota Highlander in Chesapeake, Virginia is $33,853. The average mileage on a used Toyota Highlander 2021 for sale in Chesapeake, Virginia is 65,884. Based on the average mileage of 65,884 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 $21,713.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.