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2,075 listings
- Price Drop$31,990great price$4,679 below market
- 53,756 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Southern Chrysler Dodge Jeep RAM Chesapeake (14 mi away)
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Located in Chesapeake, VA / 14 miles away from Chesapeake, VA
Certified. Celestial Silver Metallic 2023 Toyota Highlander XLE 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp 8-Speed Automatic FWD SUNROOF/MOO...
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: 5TDKDRAH8PS504793
Stock: YP10777
Certified Pre-Owned: No
Listed since: 06-16-2025 - Price Drop$28,980great price$4,076 below market
- 50,578 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Burlington Kia (186 mi away)
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Located in Burlington, NC / 186 miles away from Chesapeake, VA
Enjoy comfort, versatility, and reliability in this 2023 Toyota Highlander LE FWD, featuring a sleek Celestial Silver Metallic exterior and refined Bl...
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: 5TDKDRAH2PS509746
Stock: B4872P
Certified Pre-Owned: No
Listed since: 06-17-2025 - $33,495great price$6,520 below market
- 46,732 miles
- No accidents, 2 owners, rental vehicle
- 7 Seats, 21 City / 28 Hwy MPG
- Platinum Auto Sales of Arlington Virginia (156 mi away)
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Located in Arlington, VA / 156 miles away from Chesapeake, VA
Non-smoker owner, Vehicle Runs Well, Smooth ride, All records in possession, Regularly maintained, Lots of storage, Arctic cold a/c, No pets, Seats as...
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: 5TDKDRBH4PS507222
Stock: 507222
Certified Pre-Owned: No - Price Drop$36,669great price$4,074 below market
- 47,831 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Sir Walter Chevrolet (151 mi away)
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Located in Raleigh, NC / 151 miles away from Chesapeake, VA
2023 Toyota Highlander Limited Black ABS brakes, Active Cruise Control, Alloy wheels, Electronic Stability Control, Front dual zone A/C, Heated door m...
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 - $29,500great price$3,551 below 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 - $33,383great price$3,336 below market
- 21,995 miles
- No accidents, 1 owner, corporate fleet vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Driveway (151 mi away)
- Home delivery*
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Located in Springfield, VA / 151 miles away from Chesapeake, VA
CarFax 1-Owner,3rd Row Seat,Apple CarPlay,Back-Up Camera,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Satellite Radio,Turbo/Supercharged,W...
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: 5TDKDRAH5PS046064
Stock: 24971P
Certified Pre-Owned: No - $37,243good price$947 below market
- 40,225 miles
- No accidents, 3 owners, rental vehicle
- 7 Seats, 21 City / 28 Hwy MPG
- Bill Page Toyota (157 mi away)
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Located in Falls Church, VA / 157 miles away from Chesapeake, VA
2023 Toyota Highlander XLE Blueprint AWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hpToyota Safety Sense 2.5+: Pre-Collision...
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: 5TDKDRBH7PS046324
Stock: P8548A
Certified Pre-Owned: No
Listed since: 06-13-2025 - $39,672good price$2,312 below market
- 18,410 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Reidsville Nissan (194 mi away)
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Located in Reidsville, NC / 194 miles away from Chesapeake, VA
Your Next Ride Starts Here at Reidsville Nissan!Clean CARFAX. CARFAX One-Owner. Maroon 2023 Toyota Highlander XLE AWD 8-Speed Automatic 2.4L I4 PDI T...
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: 5TDKDRBH4PS040657
Stock: R13446
Certified Pre-Owned: No
Listed since: 06-23-2025 - $34,000good price$2,600 below market
- 32,365 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 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!** **CLEAN Carfax!** **One Owner Vehicle!** **Special Color!** **Good Miles!** **Priced to Sell!** **Heated Seats!**...
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: 5TDKDRAH5PS027451
Stock: 0N38494A
Certified Pre-Owned: No
Listed since: 07-17-2025 - Price Drop$30,800good price$2,125 below market
- 55,253 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- First Team Subaru Norfolk (9 mi away)
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Located in Norfolk, VA / 9 miles away from Chesapeake, VA
Silver 2023 Toyota Highlander L FWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hpThe 2023 Toyota Highlander LE is a popular ...
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: 5TDKDRAH5PS502757
Stock: NB1635
Certified Pre-Owned: No
Listed since: 06-23-2025 - $31,500good price$2,341 below market
- 45,241 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Koons Arlington Toyota (157 mi away)
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Located in Arlington, VA / 157 miles away from Chesapeake, VA
2023 Toyota Highlander LE 3rd row seats: split-bench, ABS brakes, Automatic temperature control, Exterior Parking Camera Rear, Power driver seat, Powe...
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: 5TDKDRAH2PS027598
Stock: KRTP230110
Certified Pre-Owned: No
Listed since: 07-11-2025 - New Listing$40,998fair price$288 below market
- 15,592 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 28 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:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH4PS029125
Stock: 27565370
Certified Pre-Owned: No - Price Drop$40,000fair price$208 below market
- 18,012 miles
- No accidents, 1 owner, personal use
- 8 Seats, 21 City / 28 Hwy MPG
- Koons Arlington Toyota (157 mi away)
Close
Located in Arlington, VA / 157 miles away from Chesapeake, VA
2023 Toyota Highlander XLE 3rd row seats: split-bench, ABS brakes, Automatic temperature control, Electronic Stability Control, Exterior Parking Camer...
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: 5TDKDRBH4PS040786
Stock: 711
Certified Pre-Owned: No
Listed since: 07-17-2025 - $40,990fair price$303 below market
- 18,829 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 28 Hwy MPG
- Carvana - Richmond (100 mi away)
- Home delivery*
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Located in Richmond, VA / 100 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: 5TDKDRBH8PS520362
Stock: 2003776743
Certified Pre-Owned: No
Listed since: 06-25-2025 - $32,000fair price$524 above market
- 58,132 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Southern Nissan Chesapeake (14 mi away)
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Located in Chesapeake, VA / 14 miles away from Chesapeake, VA
New Price! CARFAX One-Owner. Clean CARFAX.Midnight Black Metallic 2023 Toyota Highlander L FWD FWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V...
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: 5TDKDRAH3PS504393
Stock: MP10656
Certified Pre-Owned: No
Listed since: 06-18-2025 - $35,500good price$2,294 below market
- 46,360 miles
- No accidents, 1 owner, corporate fleet vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Hanna Imports (148 mi away)
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Located in Raleigh, NC / 148 miles away from Chesapeake, VA
CARFAX One-Owner. *Multi Point Inspection*, *Carfax Accident Free*, 3rd row seats: split-bench, Alloy wheels, Auto High-beam Headlights, Automatic tem...
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: 5TDKDRAH7PS020159
Stock: 3021538
Certified Pre-Owned: No
Listed since: 04-23-2025 - Price Drop$32,590fair price$252 below market
- 44,360 miles
- 1 accident, 1 owner, corporate fleet vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Carvana - Richmond (100 mi away)
- Home delivery*
Close
Located in Richmond, VA / 100 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: 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:
25 Combined MPG (22 City/29 Highway)
Listing Information:
VIN: 5TDKDRAH5PS012366
Stock: 2003769486
Certified Pre-Owned: No
Listed since: 06-10-2025 - Price Drop$33,400good price$1,764 below market
- 51,298 miles
- No accidents, 1 owner, rental vehicle
- 7 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: 5TDKDRAH2PS009067
Stock: J6830
Certified Pre-Owned: No
Listed since: 05-13-2025 - Price Drop$40,200good price$1,512 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)
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Located in Fairfax, VA / 158 miles away from Chesapeake, VA
Priced below KBB Fair Purchase Price! Clean CARFAX. Odometer is 1271 miles below market average!2023 Toyota Highlander XSE AWD Blueprint*3rd Row Sea...
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 - $36,500good price$1,253 below 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 - Price Drop$31,990fair price$653 below market
- 48,694 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Driveway (2 mi away)
- Home delivery*
Close
Located in Chesapeake, VA / 2 miles away from Chesapeake, VA
CarFax 1-Owner,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Satellite Radio,T...
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: 5TDKDRAH6PS004857
Stock: PS004857P
Certified Pre-Owned: No
Showing 1 - 21 out of 2,075 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
Hot Garbage
Koopa, 10/08/2023
2023 Toyota Highlander Limited 4dr SUV AWD (2.4L 4cyl Turbo 8A)
Stay away from the turbo 4-cyl. After about 3500-4000 miles on the odometer it performs completely different than when new. Horrible lag from the turbo and then an unexpected rush of power causing the car to behave squirrelly. The dealer will look at you like you’re nuts when you try to explain the problem as well. The infotainment is complicated and cumbersome. The seats aren’t great … and the armrest position on the drivers door is lacking. What other car company charges a monthly fee for remote start that doesn’t even stay running when you open the door? As a long time Toyota household, and a 3-time Highlander owning family, this is a very disappointing vehicle. We won’t even consider another Toyota product that doesn’t have a naturally aspirated engine because of this hot garbage. After 6k miles, we traded it in on a brand new 2023 Honda Pilot. Very happy with the Pilot.
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 | $27,744 | $29,224 | $30,892 |
| Clean | $27,396 | $28,827 | $30,440 |
| Average | $26,817 | $28,166 | $29,687 |
| Rough | $26,064 | $27,306 | $28,708 |
The average list price of a used 2023 Toyota Highlander in Chesapeake, Virginia is $34,829. The average mileage on a used Toyota Highlander 2023 for sale in Chesapeake, Virginia is 39,375. Based on the average mileage of 39,375 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 $26,817.
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