Skip to FiltersReport abuse
2,162 listings
- $31,000good price$1,274 below 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 - Price Drop$31,287good price$1,581 below market
- 52,955 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Academy Ford Sales (165 mi away)
Close
Located in Laurel, MD / 165 miles away from Chesapeake, VA
WON'T BE HERE LONG! BLACK ON BLACK HIGHLANDER WITH ONLY 53000 MILES! Clean CARFAX. Midnight Black Metallic 2021 Toyota Highlander XLE AWD 8-Speed Aut...
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: 5TDGZRBH7MS154980
Stock: 06314R
Certified Pre-Owned: No
Listed since: 02-14-2025 - $35,500good price$1,484 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$30,998fair price$1,140 below market
- 88,817 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from SC to VA*
Close
Located in Columbia, SC / 333 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: 5TDYZRAH5MS522059
Stock: 27290611
Certified Pre-Owned: No - $37,000good price$949 below market
- 38,479 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: 5TDKDRAH8PS048472
Stock: J6883
Certified Pre-Owned: No
Listed since: 05-22-2025 - Price Drop$39,386good price$2,069 below market
- 19,002 miles
- 1 accident, 1 owner, personal use
- 7 Seats, 22 City / 29 Hwy MPG
- Leith Toyota (143 mi away)
Close
Located in Raleigh, NC / 143 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 - $35,680good price$1,617 below market
- 39,665 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Farmington Hills, MI / 549 miles away from Chesapeake, VA
Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Chrome Wheels,Hands-Free Liftgate,Heated Seats,Heated St...
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: 5TDDZRBH8MS533134
Stock: MS533134A
Certified Pre-Owned: No - $39,998good price$1,982 below market
- 17,195 miles
- 1 accident, 1 owner, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to VA*
Close
Located in Inglewood, CA / 2,364 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: 5TDFZRAHXMS052621
Stock: 27280286
Certified Pre-Owned: No - New Listing$27,490good price$919 below market
- 71,453 miles
- No accidents, 3 owners, rental vehicle
- 7 Seats, 20 City / 26 Hwy MPG
- Capital Hyundai of Jacksonville (150 mi away)
Close
Located in Jacksonville, NC / 150 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:
22 Combined MPG (20 City/26 Highway)
Listing Information:
VIN: 5TDJZRFHXKS966769
Stock: 21H5684A
Certified Pre-Owned: No
Listed since: 05-31-2025 - $29,987good price$1,573 below market
- 59,343 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in New Port Richey, FL / 699 miles away from Chesapeake, VA
CarFax No Accidents Reported,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keepi...
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: 5TDGZRAH3MS533332
Stock: MS533332P
Certified Pre-Owned: No - $38,989fair price$433 below market
- 30,327 miles
- No accidents, 1 owner, personal use
- 7 Seats, 22 City / 29 Hwy MPG
- Leith Toyota (143 mi away)
Close
Located in Raleigh, NC / 143 miles away from Chesapeake, VA
Priced below KBB Fair Purchase Price! Clean CARFAX. CARFAX One-Owner. Midnight Black Metallic 2023 Toyota Highlander XLE FWD 8-Speed Automatic 2.4L I4...
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: 5TDKDRAH5PS038935
Stock: T038935A
Certified Pre-Owned: No
Listed since: 05-29-2025 - Price Drop$35,500fair price$30 above market
- 10,727 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Country Chevrolet (162 mi away)
Close
Located in Warrenton, VA / 162 miles away from Chesapeake, VA
2023 Toyota Highlander L Celestial Silver Metallic FWD 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp 8-Speed Automatic ABS brakes, Active Cruis...
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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH1PS526294
Stock: 45819B
Certified Pre-Owned: No
Listed since: 03-24-2025 - New Listing$33,998fair price$836 below market
- 47,930 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from KS to VA*
Close
Located in Wichita, KS / 1,154 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: 5TDHZRBH0MS555033
Stock: 27085179
Certified Pre-Owned: No - $24,369fair price
- 112,023 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Grapevine, TX / 1,208 miles away from Chesapeake, VA
CarFax No Accidents Reported,CarFax 1-Owner,Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Keyless Star...
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: 5TDBZRBH2MS156100
Stock: MS156100DW
Certified Pre-Owned: No - Price Drop$42,000fair price$355 below market
- 28,188 miles
- No accidents, 2 owners, personal use
- 7 Seats, 21 City / 28 Hwy MPG
- Ourisman Kia of Fairfax (158 mi away)
Close
Located in Fairfax, VA / 158 miles away from Chesapeake, VA
Clean CARFAX. Odometer is 4840 miles below market average!2023 Toyota Highlander XSE AWD Blueprint*3rd Row Seating*, Blind Spot Monitor, Backup Came...
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: 5TDKDRBH3PS000179
Stock: M2456
Certified Pre-Owned: No
Listed since: 05-07-2025 - New Listing$27,990fair price$337 below market
- 72,719 miles
- No accidents, 2 owners, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Indianapolis, IN / 578 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: 5TDBZRBH2MS124540
Stock: 2003693243
Certified Pre-Owned: No
Listed since: 05-19-2025 - $33,998fair price$142 above market
- 60,922 miles
- No accidents, 1 owner, personal use
- 8 Seats, 20 City / 27 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDHZRBH3MS554877
Stock: 27076406
Certified Pre-Owned: No - Price Drop$17,499good price$1,122 below market
- 144,198 miles
- 1 accident, 2 owners, corporate fleet vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- Supreme Motors (132 mi away)
Close
Located in Stafford, VA / 132 miles away from Chesapeake, VA
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: 5TDBZRFH1KS941537
Stock: KS941537
Certified Pre-Owned: No - $35,699good price$1,038 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 - New Listing$35,998fair price
- 35,261 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to VA*
Close
Located in Pharr, TX / 1,479 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: 5TDYZRAH0MS073437
Stock: 27041763
Certified Pre-Owned: No - Price Drop$23,782fair price$240 below market
- 105,499 miles
- No accidents, 2 owners, rental vehicle
- 7 Seats, 21 City / 27 Hwy MPG
- Terry Subaru (172 mi away)
Close
Located in Lynchburg, VA / 172 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 (21 City/27 Highway)
Listing Information:
VIN: 5TDKZRFH5KS556952
Stock: VA12425
Certified Pre-Owned: No
Listed since: 05-14-2025
Showing 232 - 252 out of 2,162 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 LE 4dr SUV (2.4L 4cyl Turbo 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $24,192 | $25,994 | $28,030 |
| Clean | $23,889 | $25,641 | $27,620 |
| Average | $23,383 | $25,053 | $26,936 |
| Rough | $22,727 | $24,288 | $26,048 |
The average list price of a used 2023 Toyota Highlander in Chesapeake, Virginia is $32,769. The average mileage on a used Toyota Highlander 2023 for sale in Chesapeake, Virginia is 56,207. Based on the average mileage of 56,207 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 $23,383.
Filters
Skip to ResultsApplied Filters4Active
Make & Model
Year
New / Used
Price & Payments
Price Rating
Body Type
Trim
Mileage
Accidents & History
Engine & Drivetrain
Exterior Color
Interior Color
Total Seating
Edmunds Review
Features
Options & Packages
MPG
* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.