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2,223 listings
- $26,500fair price$166 above market
- 64,628 miles
- No accidents, 3 owners, corporate fleet vehicle
- 8 Seats, 21 City / 29 Hwy MPG
- 1 US Motors (186 mi away)
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Located in Edgewood, MD / 186 miles away from Chesapeake, VA
Vehicle Overview: **Vehicles come with complimentary Lifetime Powertrain warranty (with Qualifying purchase) The Eprice does not include state taxes 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/29 Highway)
Listing Information:
VIN: 5TDCZRAH1LS031092
Stock: 031092
Certified Pre-Owned: No - $36,991fair price$425 above market
- 59,571 miles
- No accidents, 2 owners, rental vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- CMA's Rocky Mount Toyota (103 mi away)
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Located in Rocky Mount, NC / 103 miles away from Chesapeake, VA
Thank you for choosing CMA's Rocky Mount Toyota, this Midnight Black Metallic 2022 Toyota Highlander XLE is a great choice! Check out the following: ...
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: 5TDGZRBHXNS203199
Stock: PNS203199
Certified Pre-Owned: No
Listed since: 05-26-2025 - New Listing$31,499fair price$323 below market
- 55,004 miles
- 8 Seats, 20 City / 27 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
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Located in Concord, CA / 2,492 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDBZRBH0NS243589
Stock: 7V6WVX
Certified Pre-Owned: No
Listed since: 05-29-2025 - 36,907 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Salem, OR / 2,474 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,Chrome Wheel...
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: 5TDDZRBH8NS252811
Stock: NS252811
Certified Pre-Owned: No- Price Drop$31,427fair price$277 below market
- 80,222 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Stevenson-Hendrick Toyota Jacksonville (149 mi away)
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Located in Jacksonville, NC / 149 miles away from Chesapeake, VA
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: 5TDHZRAHXNS102542
Stock: S8975A
Certified Pre-Owned: No
Listed since: 05-10-2025 - New Listing$37,691fair price$463 below market
- 24,657 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 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
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: 5TDGZRBH0NS585873
Stock: SS583623A
Certified Pre-Owned: No - $38,977fair price$74 below market
- 42,249 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Deacon Jones Chevrolet of La Grange (133 mi away)
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Located in La Grange, NC / 133 miles away from Chesapeake, VA
Recent Arrival! Blprn 2022 Toyota Highlander Limited 3.5L V6 DOHC 8-Speed Automatic FWDOdometer is 855 miles below market average! 21/29 City/Highw...
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: 5TDYZRAH5NS542474
Stock: TH20310
Certified Pre-Owned: No
Listed since: 06-03-2025 - $42,998fair price$745 above market
- 41,823 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CO to VA*
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Located in Golden, CO / 1,578 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: 5TDFZRBH1NS229038
Stock: 25769129
Certified Pre-Owned: No - Price Drop$31,998good price$1,396 below market
- 36,625 miles
- 1 accident, 1 owner, personal use
- 8 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CT to VA*
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Located in Waterbury, CT / 375 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDBZRBH3NS563229
Stock: 27320737
Certified Pre-Owned: No - $29,991fair price
- 49,787 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Houston, TX / 1,199 miles away from Chesapeake, VA
3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Remote Start,Satellite Radio,WiF...
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: 5TDZZRAH2NS541951
Stock: NS541951A
Certified Pre-Owned: No - Price Drop$34,484fair price$477 above market
- 63,439 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Moore's Chevrolet (131 mi away)
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Located in Clarksville, VA / 131 miles away from Chesapeake, VA
AWD, 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,...
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: 5TDGZRBH4NS180356
Stock: SA180356
Certified Pre-Owned: No
Listed since: 02-18-2025 - Price Drop
- 43,798 miles
- No accidents, 1 owner, personal use
- 7 Seats, 20 City / 27 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Johnston, IA / 995 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDHZRBH5NS179642
Stock: NS179642AT
Certified Pre-Owned: No - New Listing$32,998fair price$413 below market
- 51,523 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from LA to VA*
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Located in Kenner, LA / 931 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: 5TDGZRAH1NS554083
Stock: 27074667
Certified Pre-Owned: No - Price Drop$28,495good price$1,720 below market
- 53,202 miles
- 1 accident, 1 owner, rental vehicle
- 8 Seats, 21 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Sterling Heights, MI / 541 miles away from Chesapeake, VA
Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Remote Start,Satellite...
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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDZZRAH7NS133932
Stock: NS133932KL
Certified Pre-Owned: No - New Listing$33,981fair price$235 below market
- 70,057 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Battlefield Toyota (155 mi away)
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Located in Culpeper, VA / 155 miles away from Chesapeake, VA
++TOYOTA CERTIFIED EXTENDED WARRANTY INCLUDED ++1-OWNER++ LIMITED PACKAGE++ v6++ AWD++ 2020 Toyota Highlander Limited 3.5L V6 DOHC Ruby Flare Pearl 2...
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: 5TDDZRBH7LS010136
Stock: T18925A
Certified Pre-Owned: Yes
Listed since: 06-09-2025 - $36,545fair price$816 above market
- 44,182 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- Fred Anderson Toyota of Sanford (185 mi away)
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Located in Sanford, NC / 185 miles away from Chesapeake, VA
Recent Arrival! Priced below KBB Fair Purchase Price! Odometer is 2652 miles below market average! *Available at Fred Anderson Toyota of Sanford! Call...
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: 5TDGZRAH7NS553097
Stock: SS554302A
Certified Pre-Owned: No
Listed since: 06-04-2025 - New Listing$31,998fair price$183 below market
- 77,180 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax Dulles (170 mi away)
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Located in Sterling, VA / 170 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: 5TDDZRBH1LS050907
Stock: 27485534
Certified Pre-Owned: No - Price Drop$38,997fair price$469 above market
- 63,884 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Malloy Ford (154 mi away)
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Located in Charlottesville, VA / 154 miles away from Chesapeake, VA
Make it Malloy!!!!Malloy Ford in beautiful Charlottesville, Va. Has the best value Pre Owned Used Cars, SUV's, and Trucks! Call us 4**-9**-7*** or ema...
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: 5TDFZRBH0NS238023
Stock: F24782A
Certified Pre-Owned: No
Listed since: 05-12-2025 - Price Drop$39,590fair price$134 above market
- 53,113 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Birmingham, AL / 637 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: 5TDDZRBH5NS191272
Stock: 2003750609
Certified Pre-Owned: No
Listed since: 06-04-2025 - Price Drop$42,998fair price$450 above market
- 35,765 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- CarMax (In-stock online)
- Transfer available from KS to VA*
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Located in Merriam, KS / 1,017 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:
23 Combined MPG (20 City/27 Highway)
Listing Information:
VIN: 5TDFZRBH0NS169415
Stock: 27377077
Certified Pre-Owned: No - New Listing
- 66,881 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Knoxville, TN / 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: 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: 5TDGZRBH4NS232911
Stock: 2003734595
Certified Pre-Owned: No
Listed since: 06-04-2025
Showing 421 - 441 out of 2,223 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 2020 Toyota Highlander in Chesapeake, VA Values
Estimated values
2020 Toyota Highlander L 4dr SUV (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $21,335 | $24,025 | $26,615 |
| Clean | $20,783 | $23,395 | $25,909 |
| Average | $19,862 | $22,346 | $24,732 |
| Rough | $18,665 | $20,982 | $23,203 |
The average list price of a used 2020 Toyota Highlander in Chesapeake, Virginia is $35,459. The average mileage on a used Toyota Highlander 2020 for sale in Chesapeake, Virginia is 53,071. Based on the average mileage of 53,071 for used 2020 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 2020 in Chesapeake, Virginia to be $19,862.
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