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2,076 listings
- $25,786great price$4,259 below market
- 73,546 miles
- No accidents, 2 owners, rental vehicle
- 7 Seats, 20 City / 27 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH2MS072476
Stock: SAI2840
Certified Pre-Owned: No - $26,900great price$2,339 below market
- 72,924 miles
- No accidents, 3 owners, personal use
- 7 Seats, 21 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
2021 Toyota Highlander XLE Recent Arrival! Clean CARFAX.Highlander XLE, 4D Sport Utility, 3.5L V6 DOHC, 8-Speed Automatic, FWD, Magnetic Gray, Graph...
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/29 Highway)
Listing Information:
VIN: 5TDGZRAH1MS067951
Stock: 52E2032A
Certified Pre-Owned: No
Listed since: 04-30-2025 - $30,495great price$2,404 below market
- 76,757 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Waldorf Toyota (137 mi away)
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Located in Waldorf, MD / 137 miles away from Chesapeake, VA
**Recent Arrival!** **Local Trade!** **V6!** **AWD!** **Priced to Sell!** **Premium Audio!** **Black Emblems!** **Family Fun!** **Ask For a Video Walk...
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: 5TDHZRBH7MS148584
Stock: 0N38039A
Certified Pre-Owned: Yes
Listed since: 05-02-2025 - $24,750great price$1,581 below market
- 99,693 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Koons Easton Toyota (139 mi away)
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Located in Easton, MD / 139 miles away from Chesapeake, VA
2021 Toyota Highlander LE 2021 Toyota Highlander LE in Blizzard Pearl, Please call 410-822-8000 with any equipment or availability questions!, Schedul...
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: 5TDBZRBH5MS089928
Stock: KET250059A
Certified Pre-Owned: No
Listed since: 05-05-2025 - $34,000fair price$259 below market
- 34,771 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Ourisman Honda of Tysons Corner (161 mi away)
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Located in Vienna, VA / 161 miles away from Chesapeake, VA
ONE OWNER, CLEAN CARFAX, FACTORY WARRENTY, BACKUP CAMERA / REAR VIEW CAMERA / REVERSE CAMERA, ADAPTIVE CRUISE CONTROL / ACC / DYNAMIC RADAR CRUISE CON...
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: 5TDGZRBH5MS548283
Stock: A548283
Certified Pre-Owned: No
Listed since: 04-14-2025 - Price Drop$31,390great price$2,117 below market
- 52,897 miles
- 2 accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Westgate Chrysler Jeep Dodge Ram (152 mi away)
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Located in Raleigh, NC / 152 miles away from Chesapeake, VA
CARFAX One-Owner. AWD, 3rd row seats: split-bench, Apple CarPlay/Android Auto, Power Liftgate, Power moonroof, Steering wheel mounted audio controls, ...
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: 5TDGZRBH7MS075616
Stock: 28479P
Certified Pre-Owned: No
Listed since: 12-10-2024 - Price Drop$33,895fair price$423 above market
- 39,094 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Trust Auto (193 mi away)
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Located in Sykesville, MD / 193 miles away from Chesapeake, VA
You can find this Loaded 2021 Toyota Highlander XLE 7-Passenger SUV FWD (Front Wheel Drive) and many others like it at Trust Auto. This Toyota include...
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/29 Highway)
Listing Information:
VIN: 5TDGZRAHXMS044670
Stock: 044670
Certified Pre-Owned: No
Listed since: 04-22-2025 - $27,500good price$1,530 below market
- 87,698 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Ourisman Honda of Laurel (166 mi away)
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Located in Laurel, MD / 166 miles away from Chesapeake, VA
CARFAX One-Owner. This 2021 Ruby Flare Pearl Toyota Highlander XLE AWD is well equipped and includes these features and benefits:. 8-Speed Automatic...
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: 5TDHZRBHXMS124487
Stock: MH10430
Certified Pre-Owned: No
Listed since: 05-13-2025 - $30,055good price$1,772 below 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 - $38,598fair price$1,037 above market
- 57,162 miles
- No accidents, 1 owner, corporate fleet vehicle
- 7 Seats, 21 City / 29 Hwy MPG
- Crossroads INFINITI of Raleigh (143 mi away)
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Located in Raleigh, NC / 143 miles away from Chesapeake, VA
CARFAX One-Owner. Clean CARFAX. 2021 Toyota HighlanderClean Carfax, One Owner, 20" Painted Alloy Wheels, Apple CarPlay/Android Auto, Auto High-beam He...
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: 5TDFZRAH2MS064374
Stock: PU4374
Certified Pre-Owned: No
Listed since: 04-22-2025 - New Listing$34,500good price$1,157 below market
- 65,464 miles
- No accidents, 1 owner, personal use only
- 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
CARFAX One-Owner. Clean CARFAX. Midnight Black 2021 Toyota Highlander XSE AWD 8-Speed Automatic 3.5L V6 DOHC Leather Seats, Sunroof/Moonroof, Third Ro...
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: X047846A
Certified Pre-Owned: No
Listed since: 04-12-2025 - New Listing$30,000fair price$238 below market
- 75,970 miles
- No accidents, 1 owner, personal use only
- 8 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: 5TDHZRBH2MS531137
Stock: 0252688A
Certified Pre-Owned: No
Listed since: 05-23-2025 - Price Drop$29,499fair price$115 below market
- 57,913 miles
- No accidents, 1 owner, corporate fleet vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- Bill Page Toyota (157 mi away)
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Located in Falls Church, VA / 157 miles away from Chesapeake, VA
Certified. 2021 Toyota Highlander L Blueprint AWD 8-Speed Automatic 3.5L V6 DOHCToyota Safety Sense 2.5+: Pre-Collision Sys w/Pedestrian Detection, Fu...
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: 5TDCZRBH1MS143102
Stock: P8417
Certified Pre-Owned: Yes
Listed since: 04-01-2025 - $35,900good price$1,728 below market
- 25,677 miles
- 1 accident, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Hanna Imports (148 mi away)
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Located in Raleigh, NC / 148 miles away from Chesapeake, VA
Leather Seats, Bluetooth, *Multi Point Inspection*, Highlander XLE, AWD, Apple CarPlay/Android Auto, Exterior Parking Camera Rear, Power Liftgate, Pow...
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: 5TDGZRBH1MS094422
Stock: 3021587
Certified Pre-Owned: No
Listed since: 04-27-2025 - $31,990good price$671 below market
- 99,921 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Driveway (151 mi away)
- Home delivery*
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Located in Springfield, VA / 151 miles away from Chesapeake, VA
CarFax No Accidents Reported,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Hands-Free Liftgate,Heated Seats,Heat...
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: 5TDFZRBH8MS137388
Stock: 24830P
Certified Pre-Owned: No - New Listing$28,998fair price$431 below market
- 89,969 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax Fayetteville (191 mi away)
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Located in Fayetteville, NC / 191 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDGZRAH1MS533295
Stock: 26982663
Certified Pre-Owned: No - New Listing$38,999fair price$451 below market
- 49,496 miles
- No accidents, 2 owners, rental vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Enterprise Car Sales Raleigh (150 mi away)
- Home delivery*
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Located in Raleigh, NC / 150 miles away from Chesapeake, VA
Transfer of vehicle from another location to your neighborhood Enterprise Car Sales may require payment of a non-refundable transfer fee to begin the ...
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: 5TDFZRBH5MS072791
Stock: 8DWVMN
Certified Pre-Owned: No
Listed since: 04-29-2025 - Price Drop$29,460fair price$245 below market
- 56,922 miles
- 1 accident, 2 owners, corporate fleet vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- Johnson Lexus of Raleigh (144 mi away)
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Located in Raleigh, NC / 144 miles away from Chesapeake, VA
JUST ARRIVED!! DETAILS COMING SOON!This vehicle is located at Johnson Lexus of Raleigh.Here at Johnson Lexus we price our cars online aggressively ...
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: 5TDBZRBH0MS068131
Stock: D42298B
Certified Pre-Owned: No
Listed since: 04-26-2025 - $29,994fair price$86 above market
- 74,809 miles
- 1 accident, 3 owners, rental vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Chevy Chase Acura (163 mi away)
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Located in Bethesda, MD / 163 miles away from Chesapeake, VA
2021 Highlander XLE //GOOD BRAKES//, //GOOD TIRES//, AWD. 3.5L V6 engine delivering 295 horsepower and 263 lb-ft of torque, paired with an 8-speed aut...
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: 5TDGZRBH5MS118947
Stock: RZ517116A
Certified Pre-Owned: No
Listed since: 04-16-2025 - $25,995good price$1,142 below market
- 117,297 miles
- 1 accident, 2 owners, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Master Auto Group (146 mi away)
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Located in Raleigh, NC / 146 miles away from Chesapeake, VA
All of our vehicles have been freshly serviced, inspected, and carry a clean tittle with a complimentary Carfax report. Bank and Credit Union financi...
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: 5TDGZRAHXMS061663
Stock: 061663
Certified Pre-Owned: No
Listed since: 02-11-2025 - $37,200fair price$446 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
Showing 1 - 21 out of 2,076 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 XLE 4dr SUV AWD (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $26,058 | $27,916 | $29,780 |
| Clean | $25,503 | $27,308 | $29,116 |
| Average | $24,578 | $26,294 | $28,009 |
| Rough | $23,376 | $24,975 | $26,570 |
The average list price of a used 2021 Toyota Highlander in Chesapeake, Virginia is $31,234. The average mileage on a used Toyota Highlander 2021 for sale in Chesapeake, Virginia is 69,007. Based on the average mileage of 69,007 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 $24,578.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.