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2,140 listings
- $25,995good price$1,081 below market
- 117,297 miles
- 1 accident, 2 owners, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Master Auto Group (146 mi away)
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Located in Raleigh, NC / 146 miles away from Chesapeake, VA
All of our vehicles have been freshly serviced, inspected, and carry a clean tittle with a complimentary Carfax report. Bank and Credit Union financi...
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/29 Highway)
Listing Information:
VIN: 5TDGZRAHXMS061663
Stock: 061663
Certified Pre-Owned: No
Listed since: 02-11-2025 - Price Drop$36,990fair price$305 above market
- 55,305 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- Driveway (2 mi away)
- Home delivery*
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Located in Chesapeake, VA / 2 miles away from Chesapeake, VA
CarFax No Accidents Reported,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Chrome Wheels,Hands-Free Liftgate,Hea...
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: 5TDKDRAH5PS500099
Stock: PS500099P
Certified Pre-Owned: No - $38,517fair price$705 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)
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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 - New Listing$42,195fair price$332 below market
- 24,671 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Trust Auto (193 mi away)
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Located in Sykesville, MD / 193 miles away from Chesapeake, VA
Trust Auto is pleased to be currently offering this Loaded 2023 Toyota Highlander XSE AWD 7-Passanger SUV with 24,671mi. This Toyota includes: 50 STAT...
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: 5TDKDRBH7PS001044
Stock: 001044
Certified Pre-Owned: No
Listed since: 05-09-2025 - Price Drop$30,997fair price$22 above market
- 48,203 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- EchoPark Automotive Raleigh (155 mi away)
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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: 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: 5TDKDRAHXPS501605
Stock: RPS501605
Certified Pre-Owned: No
Listed since: 04-30-2025 - New Listing$38,998fair price$387 above market
- 29,144 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- CarMax Laurel (169 mi away)
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Located in Laurel, MD / 169 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: 5TDDZRBH4MS527007
Stock: 27379089
Certified Pre-Owned: No - Price Drop$30,997fair price$7 above market
- 49,470 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- EchoPark Automotive Raleigh (155 mi away)
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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: 5TDKDRAH1PS500908
Stock: RPS500908
Certified Pre-Owned: No
Listed since: 04-30-2025 - $29,499fair price$313 above market
- 57,913 miles
- No accidents, 1 owner, corporate fleet vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- Bill Page Toyota (157 mi away)
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Located in Falls Church, VA / 157 miles away from Chesapeake, VA
Certified. 2021 Toyota Highlander L Blueprint AWD 8-Speed Automatic 3.5L V6 DOHCToyota Safety Sense 2.5+: Pre-Collision Sys w/Pedestrian Detection, Fu...
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: 5TDCZRBH1MS143102
Stock: P8417
Certified Pre-Owned: Yes
Listed since: 04-01-2025 - $41,995fair price$346 above market
- 38,386 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Waldorf Toyota (137 mi away)
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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 - New Listing$27,500fair price$795 below market
- 67,640 miles
- 1 accident, 2 owners, corporate fleet vehicle
- 8 Seats, 20 City / 27 Hwy MPG
- Ourisman Chevrolet of Rockville (168 mi away)
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Located in Rockville, MD / 168 miles away from Chesapeake, VA
Recent Arrival! This 2021 Black Toyota Highlander LE AWD is well equipped and includes these features and benefits:.20/27 City/Highway MPG Bluetooth, ...
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: 5TDBZRBH1MS114453
Stock: 5141EA
Certified Pre-Owned: No
Listed since: 05-30-2025 - New Listing$28,998fair price$928 below market
- 54,924 miles
- 8 Seats, 20 City / 27 Hwy MPG
- CarMax Brandywine (139 mi away)
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Located in Brandywine, MD / 139 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 Unavailable.
Features and Specs:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDBZRBH1MS104862
Stock: 26841282
Certified Pre-Owned: No - New Listing$39,998fair price$430 above market
- 42,719 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Midlothian (93 mi away)
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Located in Midlothian, VA / 93 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: 5TDFZRBH2MS099916
Stock: 27094145
Certified Pre-Owned: No - $37,200fair price$715 above market
- 41,538 miles
- No accidents, 2 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Lindsay Manassas Chrysler Dodge Jeep Ram (156 mi away)
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Located in Manassas, VA / 156 miles away from Chesapeake, VA
*WELL MAINTAINED*, POWER SUNROOF / SUNROOF / POWER TILT SLIDING ROOF, APPLE CARPLAY/ANDROID AUTO, BLUETOOTH, PUSH-BUTTON START, WIRELESS CHARGING, 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDLZRBH8MS074151
Stock: MP8945A
Certified Pre-Owned: No
Listed since: 05-15-2025 - Price Drop$33,921fair price$397 above market
- 38,259 miles
- No accidents, 2 owners, 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
Recent Arrival! 2023 Toyota Highlander LE Magnetic Gray Metallic AWD AutomaticBlind Spot Monitor, Backup Camera, Bluetooth, USB Ports, AUX Input, To...
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: 5TDKDRBH7PS040300
Stock: B8803
Certified Pre-Owned: No
Listed since: 05-21-2025 - $35,250fair price$478 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)
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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 - New Listing$32,900fair price$126 below market
- 57,927 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 20 City / 27 Hwy MPG
- DARCARS Toyota of Baltimore (177 mi away)
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Located in Baltimore, MD / 177 miles away from Chesapeake, VA
2021 Toyota Highlander XLE Recent Arrival! CARFAX One-Owner.Highlander XLE, 4D Sport Utility, 3.5L V6 DOHC, 8-Speed Automatic, AWD, Blueprint, Black...
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: 5TDHZRBH3MS538596
Stock: 52E2039A
Certified Pre-Owned: No
Listed since: 05-28-2025 - $18,795fair price$210 below market
- 153,237 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 21 City / 29 Hwy MPG
- Olympia Pre-Owned Auto (149 mi away)
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Located in Raleigh, NC / 149 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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDCZRAH8MS044441
Stock: 044441
Certified Pre-Owned: No - $37,998fair price$296 above market
- 40,361 miles
- No accidents, 1 owner, personal use
- 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: 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: 5TDJZRBH2MS158988
Stock: 27191974
Certified Pre-Owned: No - Price Drop$34,900fair price$495 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)
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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 - $31,251fair price$382 above market
- 65,600 miles
- No accidents, 3 owners, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- DARCARS Honda (154 mi away)
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Located in Bowie, MD / 154 miles away from Chesapeake, VA
2021 Toyota Highlander XLE Moon Dust 8-Speed AutomaticAWD, 3rd row seats: split-bench, Apple CarPlay/Android Auto, Exterior Parking Camera Rear, 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDGZRBH1MS116306
Stock: 5P2390A
Certified Pre-Owned: No
Listed since: 05-13-2025 - $37,498fair price$208 below market
- 51,540 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Toyota of Goldsboro (134 mi away)
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Located in Goldsboro, NC / 134 miles away from Chesapeake, VA
CARFAX One-Owner. Moon Dust 2023 Toyota Highlander XLE FWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp Toyota Certified, An...
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: 5TDKDRAH4PS020202
Stock: P3759
Certified Pre-Owned: Yes
Listed since: 05-13-2025
Showing 148 - 168 out of 2,140 listings
Consumer Reviews for the Toyota Highlander
Read recent reviews for the Toyota Highlander
Rolling again
Ken S, 10/28/2021
2022 Toyota Highlander Limited 4dr SUV AWD (3.5L 6cyl 8A)
Just replaced a 2018 Highlander due to accident. Of course the car is comfortable and nice to drive but I especially appreciate it after the accident. The 2018 was totaled because of a head on collision. My wife and I only had minor injuries that I attribute to the strength of the vehicle and the air bags that completely isolated us.
Used 2021 Toyota Highlander in Chesapeake, VA Values
Estimated values
2021 Toyota Highlander XLE 4dr SUV (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $27,537 | $29,751 | $31,972 |
| Clean | $26,950 | $29,102 | $31,259 |
| Average | $25,973 | $28,022 | $30,071 |
| Rough | $24,703 | $26,617 | $28,527 |
The average list price of a used 2021 Toyota Highlander in Chesapeake, Virginia is $33,923. The average mileage on a used Toyota Highlander 2021 for sale in Chesapeake, Virginia is 55,994. Based on the average mileage of 55,994 for used 2021 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 2021 in Chesapeake, Virginia to be $25,973.
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