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2,204 listings
- New Listing$39,999fair price$61 below market
- 31,286 miles
- 7 Seats, 21 City / 28 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
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Located in New Rochelle, NY / 317 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 Unavailable.
Features and Specs:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH3PS029777
Stock: 8DYJSV
Certified Pre-Owned: No
Listed since: 05-30-2025 - Price Drop
- 38,608 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Hall Toyota Virginia Beach (13 mi away)
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Located in Virginia Beach, VA / 13 miles away from Chesapeake, VA
Celestial Silver Metallic 2021 Toyota Highlander Platinum AWD 8-Speed Automatic 3.5L V6 DOHC AWD.AWD, 11 Speakers, 20" Painted Alloy Wheels, 3.003 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDFZRBH0MS100478
Stock: 24255595A
Certified Pre-Owned: No
Listed since: 05-31-2025 - New Listing$40,888fair price$246 below market
- 49,599 miles
- 7 Seats, 21 City / 28 Hwy MPG
- Sheehy Toyota of Fredericksburg (126 mi away)
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Located in Fredericksburg, VA / 126 miles away from Chesapeake, VA
AutoCheck Vehicle History Summary Unavailable.
Features and Specs:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH6PS509487
Stock: FI0084R
Certified Pre-Owned: Yes
Listed since: 04-02-2025 - Price Drop
- 21,061 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Charlotte, NC / 277 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH6PS008715
Stock: 2003773528
Certified Pre-Owned: No
Listed since: 05-30-2025 - New Listing$37,590great price
- 31,230 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Dallas, TX / 1,195 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: 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: 5TDKDRAH4RS531217
Stock: 2003628005
Certified Pre-Owned: No
Listed since: 04-17-2025 - $33,356fair price$380 above market
- 84,605 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Beyer Kia Falls Church (158 mi away)
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Located in Falls Church, VA / 158 miles away from Chesapeake, VA
AWD.Red 2021 Toyota Highlander LimitedAWD 8-Speed Automatic 3.5L V6 DOHC Recent Arrival! 20/27 City/Highway MPG
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: 5TDDZRBH1MS526607
Stock: E10748VK
Certified Pre-Owned: No
Listed since: 05-29-2025 - 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- New Listing
- 19,690 miles
- No accidents, 1 owner, corporate fleet vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Buffalo, NY / 443 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: 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: 5TDKDRBHXPS522940
Stock: 2003772375
Certified Pre-Owned: No
Listed since: 06-06-2025 - 36,833 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 28 Hwy MPG
- Pearson Toyota (34 mi away)
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Located in Newport News, VA / 34 miles away from Chesapeake, VA
2023 Toyota Highlander XSE 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp AWD WhiteAWD.21/28 City/Highway MPGWe offer Market Based Pricing, so p...
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: 5TDKDRBH3PS018746
Stock: 17211A
Certified Pre-Owned: No
Listed since: 05-24-2025- 37,123 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Classic Toyota Hampton (23 mi away)
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Located in Hampton, VA / 23 miles away from Chesapeake, VA
Moon Dust 2023 Toyota Highlander XLEOdometer is 5536 miles below market average!** SPECIAL LARGE 12.3-IN SCREEN ** **FREE OIL CHANGES AND STATE INSPEC...
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: 5TDKDRAH2PS041016
Stock: PPS041016
Certified Pre-Owned: No
Listed since: 04-24-2025- New Listing$39,768fair price$265 above market
- 29,932 miles
- 7 Seats, 21 City / 28 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Freehold, NJ / 265 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 Unavailable.
Features and Specs:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH6PS028381
Stock: FTP7342
Certified Pre-Owned: No - New Listing
- 25,747 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Miami, FL / 796 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH9PS008143
Stock: 2003743926
Certified Pre-Owned: No
Listed since: 05-26-2025 - New Listing
- 32,528 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Carvana - Richmond (99 mi away)
- Home delivery*
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Located in Richmond, VA / 99 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 - New Listing
- 26,695 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from AZ to VA*
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Located in Tolleson, AZ / 2,038 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: 5TDKDRAH1PS041573
Stock: 27450995
Certified Pre-Owned: No - Price Drop$38,990fair price$621 above market
- 30,949 miles
- No accidents, 3 owners, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Phoenix, AZ / 2,024 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: 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: 5TDKDRAH1PS003518
Stock: 2003746543
Certified Pre-Owned: No
Listed since: 06-05-2025 - New Listing
- 25,397 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 28 Hwy MPG
- Malloy Chevrolet of Alexandria (153 mi away)
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Located in Alexandria, VA / 153 miles away from Chesapeake, VA
New Price! ** Clean Carfax ** One Owner ** Heated Seats ** Moonroof ** Dual Climate Control ** Blind Spot ** Rear Cross Traffic Alert ** Wireless Char...
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: 5TDKDRBH9PS022090
Stock: MT4043
Certified Pre-Owned: No
Listed since: 03-24-2025 - 66,310 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Pearson Toyota (34 mi away)
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Located in Newport News, VA / 34 miles away from Chesapeake, VA
2023 Toyota Highlander XLE 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp AWD Midnight BlackAWD.21/28 City/Highway MPGWe offer Market Based Pric...
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: 5TDKDRBH8PS039270
Stock: N8810
Certified Pre-Owned: No
Listed since: 04-18-2025- Price Drop
- 30,092 miles
- No accidents, 1 owner, personal use
- 8 Seats, 22 City / 29 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Cleveland, OH / 440 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH1PS510239
Stock: 2003756354
Certified Pre-Owned: No
Listed since: 06-02-2025 - New Listing
- 34,824 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax West Broad (98 mi away)
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Located in Richmond, VA / 98 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: 5TDFZRBH7MS086949
Stock: 27486333
Certified Pre-Owned: No - Price Drop
- 51,604 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Casey Toyota (51 mi away)
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Located in Williamsburg, VA / 51 miles away from Chesapeake, VA
3rd Row / Third Row / 7 Seat Option, ADULT DRIVEN!, Clean Carfax, 1 Owner, LEATHER, Sunroof / Moonroof, Actual MPG rating will vary with options, driv...
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: 5TDKDRAH3PS508508
Stock: TS90211
Certified Pre-Owned: No
Listed since: 04-20-2025 - New Listing
- 33,719 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 28 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Phoenix, AZ / 2,024 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:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH3PS026300
Stock: 2003727664
Certified Pre-Owned: No
Listed since: 05-14-2025
Showing 400 - 420 out of 2,204 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 AWD (2.4L 4cyl Turbo 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $32,906 | $34,860 | $37,064 |
| Clean | $32,493 | $34,387 | $36,521 |
| Average | $31,806 | $33,598 | $35,618 |
| Rough | $30,913 | $32,572 | $34,443 |
The average list price of a used 2023 Toyota Highlander in Chesapeake, Virginia is $39,337. The average mileage on a used Toyota Highlander 2023 for sale in Chesapeake, Virginia is 36,507. Based on the average mileage of 36,507 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 $31,806.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.