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1,877 listings
- $40,998good price$2,781 below market
- 15,876 miles
- No accidents, 2 owners, corporate fleet vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TN to VA*
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Located in Bristol, TN / 334 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: 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: 5TDKDRAH7PS034725
Stock: 26641419
Certified Pre-Owned: No - New ListingNot Priced
- 65,052 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- John Hiester Chrysler Dodge Jeep Ram of Sanford (185 mi away)
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Located in Sanford, NC / 185 miles away from Chesapeake, VA
3.003 Axle Ratio, 3rd row seats: split-bench, 4-Wheel Disc Brakes, 6 Speakers, ABS brakes, Air Conditioning, Alloy wheels, AM/FM radio: SiriusXM, Appl...
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: 5TDHZRAH4NS127856
Stock: SR3764C
Certified Pre-Owned: No
Listed since: 05-30-2025 - 26,794 miles
- 1 accident, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Charlottesville (151 mi away)
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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: 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: 5TDGZRBH5NS167051
Stock: 27320342
Certified Pre-Owned: No- $25,786great price$4,644 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 - 43,220 miles
- 1 accident, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Nationwide Nissan (188 mi away)
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Located in Timonium, MD / 188 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDHZRBH1NS576720
Stock: 16394P
Certified Pre-Owned: No
Listed since: 04-28-2025- New Listing
- 96,504 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- John Hiester Chrysler Jeep Dodge Ram (170 mi away)
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Located in Lillington, NC / 170 miles away from Chesapeake, VA
ONE OWNER ACCIDENT FREE CARFAX, AWD, FAST AND EASY FINANCING, THE NEW PRICE OUTLET, AWD, 3.003 Axle Ratio, 3rd row seats: split-bench, 4-Wheel Disc Br...
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: 5TDHZRBH8NS180221
Stock: P10077
Certified Pre-Owned: No
Listed since: 05-28-2025 - 61,860 miles
- Frame damage reported, 2 owners, personal use only
- 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: 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 (20 City/27 Highway)
Listing Information:
VIN: 5TDJZRBH5NS175690
Stock: 35474
Certified Pre-Owned: No- Price Drop$34,999great price$3,731 below market
- 16,083 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Wexford, PA / 339 miles away from Chesapeake, VA
CarFax No Accidents Reported,CarFax 1-Owner,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH0PS048174
Stock: H048174A
Certified Pre-Owned: No - $33,976good price$2,331 below market
- 19,052 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 28 Hwy MPG
- RubyCar - Southern California (In-stock online)
- Home delivery*
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Located in San Diego, CA / 2,319 miles away from Chesapeake, VA
Priced below KBB Fair Purchase Price! Clean CARFAX. CARFAX One-Owner. RubyCar by Avis is a national online retailer that allows you to shop thousands ...
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: 5TDKDRBH1PS032256
Stock: 52244312
Certified Pre-Owned: No
Listed since: 03-21-2024 - New ListingNot Priced
- Not provided
- 8 Seats, 20 City / 27 Hwy MPG
- DARCARS Toyota of Silver Spring (166 mi away)
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Located in Silver Spring, MD / 166 miles away from Chesapeake, VA
2022 Toyota Highlander LE Recent Arrival!Magnetic Gray Metallic AWD. AWD 3.5L V6 DOHC 8-Speed Automatic 20/27 City/Highway MPG
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDBZRBH3NS568737
Stock: 52A5520A
Certified Pre-Owned: No
Listed since: 05-31-2025 - $33,887great price$3,429 below market
- 26,983 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Norris Ford (177 mi away)
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Located in Baltimore, MD / 177 miles away from Chesapeake, VA
*****2023 TOYOTA HIGHLANDER XLE*****CARFAX One-Owner. Only 26,000 miles on this like new SUV. CALL-4**-5**-3***.LEATHER, HEATED SEATS, 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH9PS047718
Stock: SB103042A
Certified Pre-Owned: No
Listed since: 04-19-2025 - $38,000great price$3,150 below market
- 41,992 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 28 Hwy MPG
- Safford Brown Dulles Nissan (171 mi away)
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Located in Sterling, VA / 171 miles away from Chesapeake, VA
Clean CARFAX. CARFAX One-Owner. Midnight Black Metallic 2023 Toyota Highlander Limited AWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-S...
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: 5TDKDRBH7PS032133
Stock: A151
Certified Pre-Owned: No
Listed since: 02-15-2025 - $30,495great price$2,821 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 - $34,800great price
- 27,216 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Houston, TX / 1,210 miles away from Chesapeake, VA
3rd Row Seat,Apple CarPlay,Back-Up Camera,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Satellite Radio,Turbo/Supercharged,WiFi Hotspot,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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH9PS009860
Stock: PS009860A
Certified Pre-Owned: No - New Listing$31,998good price$1,944 below market
- 33,372 miles
- No accidents, 1 owner, personal use
- 8 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from WA to VA*
Close
Located in Lynnwood, WA / 2,437 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH8PS004021
Stock: 27194782
Certified Pre-Owned: No - Price Drop$35,550great price$2,751 below market
- 43,357 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Leith Auto Park Kia (138 mi away)
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Located in Wendell, NC / 138 miles away from Chesapeake, VA
Clean CARFAX. CARFAX One-Owner. Gray 2023 Toyota Highlander XLE FWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp22/29 City/H...
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: 5TDKDRAH0PS040964
Stock: AK7739B
Certified Pre-Owned: No
Listed since: 04-22-2025 - $33,998great price$5,168 below market
- 37,938 miles
- No accidents, 3 owners, personal use only
- 8 Seats, 21 City / 28 Hwy MPG
- CarMax (In-stock online)
- Transfer available from GA to VA*
Close
Located in Norcross, GA / 487 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/28 Highway)
Listing Information:
VIN: 5TDKDRBH3PS014373
Stock: 27447376
Certified Pre-Owned: No - $24,750great price$1,902 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 - $30,998good price$1,754 below market
- 48,674 miles
- No accidents, 2 owners, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from NC to VA*
Close
Located in Pineville, NC / 284 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: 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: 5TDKDRAH5PS014165
Stock: 27282020
Certified Pre-Owned: No - New Listing$27,998great price$2,729 below market
- 99,428 miles
- 2 accidents, 1 owner, personal use only
- 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: 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: 5TDDZRBHXMS141904
Stock: 27449558
Certified Pre-Owned: No - Price Drop$33,500good price$1,077 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)
Close
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
Showing 169 - 189 out of 1,877 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 XLE 4dr SUV (2.4L 4cyl Turbo 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $28,926 | $30,619 | $32,527 |
| Clean | $28,564 | $30,203 | $32,051 |
| Average | $27,960 | $29,510 | $31,258 |
| Rough | $27,175 | $28,609 | $30,227 |
The average list price of a used 2023 Toyota Highlander in Chesapeake, Virginia is $33,684. The average mileage on a used Toyota Highlander 2023 for sale in Chesapeake, Virginia is 49,408. Based on the average mileage of 49,408 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 $27,960.
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