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2,076 listings
- $33,519fair price$72 below market
- 41,307 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Passport Toyota (150 mi away)
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Located in Suitland, MD / 150 miles away from Chesapeake, VA
2023 Toyota Highlander LE Midnight Black AWD AutomaticBlind Spot Monitor, Backup Camera, Bluetooth, USB Ports, AUX Input, Toyota Safety Sense, Apple...
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: 5TDKDRBH4PS041632
Stock: B8780
Certified Pre-Owned: No
Listed since: 05-07-2025 - $35,500good price$1,802 below market
- 51,298 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Haley Certified Preowned (90 mi away)
Close
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: 5TDKDRAH2PS009067
Stock: J6830
Certified Pre-Owned: No
Listed since: 05-13-2025 - New Listing$33,890fair price$719 below market
- 26,062 miles
- 8 Seats, 22 City / 29 Hwy MPG
- Passport Toyota (150 mi away)
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Located in Suitland, MD / 150 miles away from Chesapeake, VA
Certified. 2023 Toyota Highlander LE Wind Chill Pearl FWD AutomaticToyota Gold Certified, Blind Spot Monitor, Backup Camera, Bluetooth, USB Ports, A...
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH5PS021990
Stock: 27684A
Certified Pre-Owned: Yes
Listed since: 04-26-2025 - $31,000good price$1,463 below market
- 52,956 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Haley Certified Preowned (90 mi away)
Close
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: 5TDKDRAH4PS502376
Stock: J6880
Certified Pre-Owned: No
Listed since: 05-22-2025 - Price Drop$39,521fair price$908 below market
- 19,002 miles
- 1 accident, 1 owner, personal use
- 7 Seats, 22 City / 29 Hwy MPG
- Leith Toyota (142 mi away)
Close
Located in Raleigh, NC / 142 miles away from Chesapeake, VA
CARFAX One-Owner. Celestial Silver Metallic 2023 Toyota Highlander XLE FWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp LOCA...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH3PS524675
Stock: T524675P
Certified Pre-Owned: Yes
Listed since: 05-13-2025 - $31,500fair price$743 below market
- 55,424 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Haley Certified Preowned (90 mi away)
Close
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: 5TDKDRAH8PS500114
Stock: J6879
Certified Pre-Owned: No
Listed since: 05-22-2025 - Price Drop$35,599good price$1,503 below market
- 39,039 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- 355 Toyota (172 mi away)
Close
Located in Rockville, MD / 172 miles away from Chesapeake, VA
Just in: the 2023 Toyota Highlander XLE in striking Cypress green. Its stylish, spacious, and smoother than your favorite playlist. With a turbocharge...
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: 5TDKDRAH1PS505719
Stock: 52J2046A
Certified Pre-Owned: No
Listed since: 05-15-2025 - Price Drop$37,002fair price$834 below market
- 42,393 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Haley Toyota of Richmond (91 mi away)
Close
Located in Midlothian, VA / 91 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: 5TDKDRAH5PS008592
Stock: J6832
Certified Pre-Owned: No
Listed since: 05-13-2025 - Price Drop
- 48,269 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Hampton Chevrolet (23 mi away)
- Home delivery*
Close
Located in Hampton, VA / 23 miles away from Chesapeake, VA
CARFAX One-Owner. Clean CARFAX. Silver 2023 Toyota Highlander XLEAt First Team Chevrolet Enjoy Your Ride with:- NO COST OIL CHANGES FOREVER!- NO ...
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: 5TDKDRAH9PS008403
Stock: PB11968
Certified Pre-Owned: No
Listed since: 04-16-2025 - $38,517fair price$577 above market
- 39,293 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 28 Hwy MPG
- Len Stoler Lexus (190 mi away)
Close
Located in Owings Mills, MD / 190 miles away from Chesapeake, VA
CARFAX One-Owner.Midnight Black Metallic 2023 Toyota Highlander XLE AWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hpAWD, ABS...
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: 5TDKDRBH0PS023516
Stock: L1977A
Certified Pre-Owned: No
Listed since: 04-02-2025 - $41,633fair price$257 above market
- 29,286 miles
- No accidents, 3 owners, corporate fleet vehicle
- 7 Seats, 21 City / 28 Hwy MPG
- Honda of Owings Mills (187 mi away)
Close
Located in Owings Mills, MD / 187 miles away from Chesapeake, VA
Ruby Flare Pearl exterior and BLACK interior. Heated Seats, Moonroof, Third Row Seat, Power Liftgate, Turbo Charged Engine, All Wheel Drive, Aluminum ...
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: 5TDKDRBHXPS510710
Stock: PS510710
Certified Pre-Owned: No
Listed since: 05-17-2025 - Price Drop$31,997fair price$949 above market
- 45,420 miles
- No accidents, 2 owners, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- EchoPark Automotive Raleigh (155 mi away)
Close
Located in Cary, NC / 155 miles away from Chesapeake, VA
At EchoPark, it’s all about offering you options for a happy experience. We have thousands of new-to-you makes and models that range from sedans to tr...
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: 5TDKDRAH6PS505053
Stock: CPS505053
Certified Pre-Owned: No
Listed since: 04-29-2025 - $41,995fair price$520 above market
- 38,386 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Waldorf Toyota (137 mi away)
Close
Located in Waldorf, MD / 137 miles away from Chesapeake, VA
**Recent Arrival!** **AWD!** **Local Trade!** **Good Miles!** **Priced to Sell!** **Look at That Color Combination!** **Toyota Safety Sense!** **Famil...
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: 5TDKDRBH1PS018762
Stock: 00081415
Certified Pre-Owned: No
Listed since: 05-21-2025 - $32,000fair price$164 above market
- 55,314 miles
- No accidents, 2 owners, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Haley Certified Preowned (90 mi away)
Close
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: 5TDKDRAH3PS008994
Stock: J6710
Certified Pre-Owned: No
Listed since: 04-04-2025 - $35,250fair price$93 above market
- 48,972 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- DARCARS Toyota of Silver Spring (166 mi away)
Close
Located in Silver Spring, MD / 166 miles away from Chesapeake, VA
2023 Toyota Highlander XLE CARFAX One-Owner. Clean CARFAX.Cypress FWD 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp 8-Speed Automatic Priced ...
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: 5TDKDRAH8PS500968
Stock: E1F0251
Certified Pre-Owned: No
Listed since: 04-07-2025 - $35,400fair price$953 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)
Close
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$44,998fair price$868 above market
- 16,708 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- CarMax Capital Boulevard (142 mi away)
Close
Located in Raleigh, NC / 142 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/28 Highway)
Listing Information:
VIN: 5TDKDRBH5PS016822
Stock: 27249604
Certified Pre-Owned: No - $37,390fair price$23 above market
- 72,538 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Driveway (151 mi away)
- Home delivery*
Close
Located in Springfield, VA / 151 miles away from Chesapeake, VA
CarFax 1-Owner,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keeping Assist,Remo...
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: 5TDKDRBH0PS507105
Stock: SS188143A
Certified Pre-Owned: No - New Listing$37,495fair price$479 above market
- 52,741 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Waldorf Toyota (137 mi away)
Close
Located in Waldorf, MD / 137 miles away from Chesapeake, VA
**Navigation** **Recent Arrival!** **CLEAN Carfax!** **Local Trade!** **AWD!** **Special Color!** **Family Fun!** **Priced to Sell!** **Ask For a Vide...
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: 5TDKDRBH5PS043051
Stock: 00081418
Certified Pre-Owned: No
Listed since: 05-24-2025 - 2,834 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Hyman Bros. Automobiles West Broad (95 mi away)
Close
Located in Richmond, VA / 95 miles away from Chesapeake, VA
- Options: RADIO: 12.3 TOYOTA AUDIO MULTIMEDIA
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: 5TDKDRAH5PS520983
Stock: H9484
Certified Pre-Owned: No
Listed since: 02-20-2025- Price Drop$36,868fair price$586 above market
- 43,741 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Haley Toyota of Richmond (91 mi away)
Close
Located in Midlothian, VA / 91 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: 5TDKDRAH6PS009718
Stock: J6831
Certified Pre-Owned: No
Listed since: 05-13-2025
Showing 43 - 63 out of 2,076 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
Love the vehicle, Infotainment is unusable
bbells, 04/16/2023
2023 Toyota Highlander LE 4dr SUV (2.4L 4cyl Turbo 8A)
Love the gas mileage, 30+mpg in eco mode. Towing capacity. Comfort. Nice vehicle except the "drive connect" app advertisement makes the entertainment system unusable. It will lock up the system for 1 to 10 minutes so no music, no google maps, no phone, nothing, until it decides to clear itself. Toyota says you can pay $200 a year to remove the advertisement by subscribing to drive … connect. This makes it the definition of ransomware. But there is nothing in the app I need or want. Neither ToyotaUSA, their tech department, or the dealer can fix it. I will either be selling the vehicle or replacing the entertainment system when the free trial of drive connect ends in a couple months. For those of us who use their phone for maps, texts or communication the system makes the vehicle unusable. Update: Can't put in different infotainment system, it is integrated into the vehicle. Toyota gave me a free trial of drive connect. Unfortunately anytime i am in an area without internet the display is locked up asking for a password. Can't enter a password until i get into an internet area, then go s back to asking for a password when i leave it. Worthless and unusable. Toyota wouldn't fix it. After 7 months they bought it back from me. Last Toyota.
Used 2023 Toyota Highlander in Chesapeake, VA Values
Estimated values
2023 Toyota Highlander LE 4dr SUV AWD (2.4L 4cyl Turbo 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $27,855 | $29,918 | $32,246 |
| Clean | $27,506 | $29,512 | $31,774 |
| Average | $26,924 | $28,835 | $30,988 |
| Rough | $26,168 | $27,954 | $29,966 |
The average list price of a used 2023 Toyota Highlander in Chesapeake, Virginia is $36,717. The average mileage on a used Toyota Highlander 2023 for sale in Chesapeake, Virginia is 41,641. Based on the average mileage of 41,641 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 $26,924.
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