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2,204 listings
- $40,499fair price$98 above market
- 47,831 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Sir Walter Chevrolet (152 mi away)
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Located in Raleigh, NC / 152 miles away from Chesapeake, VA
Recent Arrival! 2023 Toyota Highlander Limited Black ABS brakes, Active Cruise Control, Alloy wheels, Electronic Stability Control, Front dual zone 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH8PS002821
Stock: PX6438
Certified Pre-Owned: No
Listed since: 06-02-2025 - $33,500fair price$493 above market
- 45,722 miles
- No accidents, 1 owner, rental vehicle
- 8 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: 5TDKDRAH0PS010542
Stock: J6882
Certified Pre-Owned: No
Listed since: 05-22-2025 - Price Drop$33,680fair price$57 above market
- 51,759 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Westcott Buick GMC (186 mi away)
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Located in Burlington, NC / 186 miles away from Chesapeake, VA
Priced below KBB Fair Purchase Price!2021 Toyota Highlander XLE Blue*Carfax Accident Free*, LEATHER, NAVIGATION, BLUETOOTH, SUNROOF, 3rd ROW SEATING, ...
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: 5TDHZRBH7MS089696
Stock: 25114A
Certified Pre-Owned: No
Listed since: 04-08-2025 - New Listing$26,491fair price$120 below market
- 78,894 miles
- No accidents, 3 owners, personal use
- 8 Seats, 21 City / 29 Hwy MPG
- Ourisman Fairfax Toyota (158 mi away)
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Located in Fairfax, VA / 158 miles away from Chesapeake, VA
Black 2021 Toyota Highlander LE FWD 8-Speed Automatic 3.5L V6 DOHC CERTIFIED 7 YEAR/ 100,000 MILE WARRANTY.Our best available bank and credit union...
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: 5TDZZRAH1MS517588
Stock: 13170PP
Certified Pre-Owned: No
Listed since: 06-06-2025 - Price Drop$34,500fair price$113 above market
- 53,476 miles
- No accidents, 2 owners, rental vehicle
- 7 Seats, 22 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
2023 Toyota Highlander XLE CARFAX One-Owner. Clean CARFAX.Highlander XLE, 4D Sport Utility, 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp, 8-...
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: 5TDKDRAH7PS500086
Stock: E1E0140
Certified Pre-Owned: No
Listed since: 05-01-2025 - New Listing$21,000good price$1,236 below market
- 89,000 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 20 City / 24 Hwy MPG
- Ourisman Hyundai of Bowie (153 mi away)
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Located in Bowie, MD / 153 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:
22 Combined MPG (20 City/24 Highway)
Listing Information:
VIN: 5TDZARFHXKS060163
Stock: 060163A
Certified Pre-Owned: No
Listed since: 06-08-2025 - $33,900fair price$292 above market
- 38,259 miles
- No accidents, 2 owners, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Passport Toyota (149 mi away)
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Located in Suitland, MD / 149 miles away from Chesapeake, VA
2023 Toyota Highlander LE Magnetic Gray Metallic AWD AutomaticBlind Spot Monitor, Backup Camera, Bluetooth, USB Ports, AUX Input, Toyota Safety Sens...
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: 5TDKDRBH7PS040300
Stock: B8803
Certified Pre-Owned: No
Listed since: 05-21-2025 - $37,807fair price$693 above market
- 37,876 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- FC Auto Sales & Service (158 mi away)
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Located in Falls Church, VA / 158 miles away from Chesapeake, VA
Non Smoker, Freshly Detailed, Fresh Oil Change & VA State Inspection, Local Trade, AWD, 6 Speakers, Air Conditioning, AM/FM radio: SiriusXM, Apple Car...
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: 5TDLZRBH4MS079301
Stock: 079301
Certified Pre-Owned: No
Listed since: 03-16-2025 - $39,499fair price$233 above market
- 39,040 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
++TOYOTA CERTIFIED EXTENDED WARRANTY INCLUDED ++1-OWNER++ XLE PACKAGE++ LEATHER++ SECOND ROW BENCH SEAT++ AWD++ 2023 Toyota Highlander XLE 2.4L I4 PDI...
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: Yes
Listed since: 05-27-2025 - Price Drop$35,998fair price$401 above market
- 39,816 miles
- No accidents, 2 owners, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from DE to VA*
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Located in Newark, DE / 205 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: Yes
Features and Specs:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDJZRAH4MS045982
Stock: 27223419
Certified Pre-Owned: No - Price Drop$31,998fair price$188 above market
- 56,541 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from GA to VA*
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Located in Kennesaw, GA / 507 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: Yes
Features and Specs:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDGZRAH8MS537876
Stock: 27186899
Certified Pre-Owned: No - New Listing$29,998good price$1,418 below market
- 80,462 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TN to VA*
Close
Located in Jackson, TN / 708 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDLZRAH1MS084991
Stock: 27043189
Certified Pre-Owned: No - $35,985fair price$871 above market
- 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: * 160 Point Inspection * Powertrain Limited Warranty: 84 Month/100,000 Mile (whichever comes first) from TCUV purc...
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 - New Listing$33,952good price$1,287 below market
- 83,548 miles
- 7 Seats, 20 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Calabasas, CA / 2,377 miles away from Chesapeake, VA
CarFax No Accidents Reported,Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Hands-Free Liftgate,Heated ...
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDFZRBH3MS070036
Stock: MS070036P
Certified Pre-Owned: No - Price Drop$35,998fair price$229 above market
- 41,521 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to VA*
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Located in Sacramento, CA / 2,451 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: Yes
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDHZRBH4MS523671
Stock: 27044547
Certified Pre-Owned: No - $31,588fair price$412 above market
- 71,909 miles
- No accidents, 1 owner, corporate fleet vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Oxford Car and Truck (136 mi away)
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Located in Oxford, NC / 136 miles away from Chesapeake, VA
At Oxford Car & Truck, every vehicle undergoes a meticulous hand-picking process and rigorous quality and safety inspection. Enjoy peace of mind with ...
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: 5TDGZRBH2MS148228
Stock: 6499
Certified Pre-Owned: No
Listed since: 01-16-2025 - New Listing$30,500fair price$59 below market
- 49,137 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- Apple Ford Lincoln (172 mi away)
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Located in Columbia, MD / 172 miles away from Chesapeake, VA
Recent Arrival! *FORD CERTIFIED*, *INCLUDES WARRANTY*, *CARFAX ONE OWNER*, *CARFAX ONE OWNER...NO ACCIDENTS*, *BLUE TOOTH*, *BLIND SPOT MONITOR*, *BAC...
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: 5TDBZRBHXMS531988
Stock: 257145A
Certified Pre-Owned: No
Listed since: 06-08-2025 - $30,998fair price
- 56,962 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to VA*
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Located in San Antonio, TX / 1,381 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: Yes
Features and Specs:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDGZRAH2MS048227
Stock: 27295064
Certified Pre-Owned: No - $38,890fair price$952 above market
- 21,107 miles
- No accidents, 1 owner, personal use only
- 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
Heres your official invite to upgrade family life with horsepower: the 2023 Toyota Highlander XLE. Its got room for the whole crew, plus a few tagalon...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH3PS513241
Stock: 52J2052A
Certified Pre-Owned: No
Listed since: 05-31-2025 - New Listing$30,998fair price$785 above market
- 54,596 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 26 Hwy MPG
- CarMax Wilmington (195 mi away)
Close
Located in Wilmington, NC / 195 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: 5TDJZRFH5KS593205
Stock: 27524329
Certified Pre-Owned: No - Price Drop
- 44,649 miles
- No accidents, 2 owners, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to VA*
Close
Located in Roseville, CA / 2,439 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: Yes
Features and Specs:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDJZRAH7MS080919
Stock: 26979992
Certified Pre-Owned: No
Showing 337 - 357 out of 2,204 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 2023 Toyota Highlander in Chesapeake, VA Values
Estimated values
2023 Toyota Highlander L 4dr SUV (2.4L 4cyl Turbo 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $24,228 | $25,682 | $27,321 |
| Clean | $23,925 | $25,333 | $26,921 |
| Average | $23,419 | $24,752 | $26,255 |
| Rough | $22,761 | $23,996 | $25,389 |
The average list price of a used 2023 Toyota Highlander in Chesapeake, Virginia is $33,513. The average mileage on a used Toyota Highlander 2023 for sale in Chesapeake, Virginia is 53,369. Based on the average mileage of 53,369 for used 2023 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 2023 in Chesapeake, Virginia to be $23,419.
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