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2,509 listings
- New Listing$31,998good price$1,255 below market
- 53,516 miles
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax Clermont (163 mi away)
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Located in Clermont, FL / 163 miles away from Naples, FL
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:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDLZRAH4MS036062
Stock: 27300021
Certified Pre-Owned: No - Price Drop$42,200fair price$1,001 above market
- 29,443 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Beaver Toyota of St. Augustine (254 mi away)
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Located in Saint Augustine, FL / 254 miles away from Naples, FL
CARFAX One-Owner. Certified. EXCLUSIVE BEAVER CERTIFIED 7Year/100,000 Powertrain and 12 mos/12,000 mile Bumper to Bumper Included, 7 Year/Up To 100,00...
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: 5TDKDRAH1PS505283
Stock: A20173C
Certified Pre-Owned: No
Listed since: 05-10-2025 - $38,890fair price$1,246 above market
- 36,191 miles
- No accidents, 2 owners, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- Keith Pierson Toyota (278 mi away)
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Located in Jacksonville, FL / 278 miles away from Naples, FL
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: 5TDKDRAH7PS017200
Stock: 250861A
Certified Pre-Owned: No
Listed since: 05-16-2025 - Price Drop$29,990fair price$699 below market
- 73,161 miles
- 1 accident, 2 owners, corporate fleet vehicle
- 7 Seats, 20 City / 27 Hwy MPG
- Mercedes-Benz of Orlando (171 mi away)
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Located in Maitland, FL / 171 miles away from Naples, FL
Sun/Moonroof3rd Row SeatLane Keeping AssistKeyless StartRear Spoiler50 State EmissionsBlack; Softex Seat TrimCelestial Silver MetallicThis v...
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: 5TDGZRBH9MS068909
Stock: MS068909
Certified Pre-Owned: No
Listed since: 05-20-2025 - 37,597 miles
- No accidents, 2 owners, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- AutoNation Honda Hollywood (94 mi away)
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Located in Hollywood, FL / 94 miles away from Naples, FL
The following items have been reconditioned on this vehicle: all new tires! Sun/Moonroof3rd Row SeatSpecial ColorLane Keeping AssistKeyless Sta...
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: 5TDGZRAH1MS075726
Stock: MS075726
Certified Pre-Owned: No
Listed since: 04-13-2025- $31,000good price$1,608 below market
- 42,178 miles
- 1 accident, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Las Vegas, NV / 2,085 miles away from Naples, FL
CarFax 1-Owner,Rare Find,3rd Row Seat,Apple CarPlay,Back-Up Camera,Bluetooth,Brake Assist,Keyless Start,Lane Keeping Assist,Satellite Radio,Turbo/Supe...
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: 5TDKDRAH4PS503026
Stock: N503026P
Certified Pre-Owned: No - $43,998fair price$580 above market
- 26,543 miles
- No accidents, 1 owner, personal use
- 7 Seats, 21 City / 28 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to FL*
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Located in Fresno, CA / 2,344 miles away from Naples, FL
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: 5TDKDRBH9PS509595
Stock: 27143625
Certified Pre-Owned: No - $30,495good price$1,571 below market
- 95,013 miles
- 1 accident, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Tallahassee Dodge Chrysler Jeep Ram FIAT (336 mi away)
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Located in Tallahassee, FL / 336 miles away from Naples, FL
Big Value! 2023 Toyota Highlander XLE FWD Loaded & Priced Right!THIRD ROW, MOONROOF, HEATED SEATS, APPLE CARPLAY, TOYOTA SAFETY SENSE, 95K MILES, CLEA...
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: 5TDKDRAH5PS003294
Stock: A003294
Certified Pre-Owned: No
Listed since: 02-01-2025 - New Listing$42,986fair price
- 27,170 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Odessa, TX / 1,308 miles away from Naples, FL
CarFax No Accidents Reported,CarFax 1-Owner,3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Chrome Wheels,Hands-Fr...
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: 5TDKDRAH1PS507499
Stock: PS507499C
Certified Pre-Owned: No - Price Drop$38,927fair price$921 below market
- 27,527 miles
- 1 accident, 2 owners, personal use
- 7 Seats, 21 City / 28 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
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Located in Farmington Hills, MI / 1,129 miles away from Naples, FL
3rd Row Seat,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Keyless Start,Lane Keeping Assist,Remote Start,Satell...
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: 5TDKDRBH8PS034117
Stock: PS034117A
Certified Pre-Owned: No - $32,998fair price$276 above market
- 41,482 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax Orlando (160 mi away)
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Located in Orlando, FL / 160 miles away from Naples, FL
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: 5TDHZRAHXMS525281
Stock: 27321660
Certified Pre-Owned: No - Price Drop$34,589fair price$677 above market
- 38,372 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 21 City / 28 Hwy MPG
- Palm Chevrolet Ocala (208 mi away)
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Located in Ocala, FL / 208 miles away from Naples, FL
Clean CARFAX. This 2023 Toyota Highlander LE in Wind Chill Pearl features: AWD Highlander LE, 4D Sport Utility, 2.4L I4 PDI Turbocharged DOHC 16V LEV3...
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: 5TDKDRBH1PS039806
Stock: PT2949
Certified Pre-Owned: No
Listed since: 03-14-2025 - Price Drop$29,953good price$1,131 below market
- 57,539 miles
- 1 accident, 1 owner, personal use only
- 8 Seats, 21 City / 29 Hwy MPG
- AutoNation Honda Sanford (182 mi away)
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Located in Sanford, FL / 182 miles away from Naples, FL
Sun/Moonroof3rd Row SeatLane Keeping AssistKeyless StartRear Spoiler2Nd Row Bench Seat50 State EmissionsCelestial Silver MetallicGraphite; Sof...
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: 5TDGZRAHXMS031742
Stock: MS031742
Certified Pre-Owned: No
Listed since: 05-10-2025 - $33,998fair price$98 above market
- 31,063 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from AZ to FL*
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Located in Gilbert, AZ / 1,861 miles away from Naples, FL
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: 5TDKDRAH9PS501045
Stock: 27451006
Certified Pre-Owned: No - 30,408 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- CarMax (In-stock online)
- Transfer available from UT to FL*
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Located in South Jordan, UT / 1,990 miles away from Naples, FL
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: 5TDKDRBH8PS512388
Stock: 27214326
Certified Pre-Owned: No- $42,998fair price
- 30,453 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to FL*
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Located in Pharr, TX / 1,020 miles away from Naples, FL
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: 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: 5TDKDRAH3PS034060
Stock: 27424519
Certified Pre-Owned: No - Price Drop
- 33,719 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 21 City / 28 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
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Located in Phoenix, AZ / 1,881 miles away from Naples, FL
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 - Price Drop$32,999fair price$128 above market
- 44,405 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
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Located in Scottsdale, AZ / 1,872 miles away from Naples, FL
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
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: 5TDKDRAH4PS522465
Stock: 8FSQWL
Certified Pre-Owned: No
Listed since: 04-10-2025 - $36,659fair price$655 above market
- 55,968 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Nimnicht Chevrolet (284 mi away)
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Located in Jacksonville, FL / 284 miles away from Naples, FL
EquipmentThis Toyota Highlander offers Automatic Climate Control for personalized comfort. This model's blind spot monitor enhances safety. Our dealer...
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: 5TDKDRAH6PS040029
Stock: 25C674D
Certified Pre-Owned: No
Listed since: 05-07-2025 - Price Drop
- 41,518 miles
- Frame damage reported, 1 owner, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- North Miami Mitsubishi (95 mi away)
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Located in Miami Gardens, FL / 95 miles away from Naples, FL
2021 Toyota Highlander XLE Celestial Silver Metallic 4D Sport Utility 3.5L V6 DOHCForward collision alert, Keyless start, Lane tracing assist, Lane ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Issue reported
Salvage Vehicle: No
Frame Damage: Yes
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
24 Combined MPG (21 City/29 Highway)
Listing Information:
VIN: 5TDGZRAH8MS536758
Stock: 536758F01
Certified Pre-Owned: No
Listed since: 04-02-2025 - $42,998fair price
- 31,762 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to FL*
Close
Located in San Antonio, TX / 1,054 miles away from Naples, FL
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: 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: 5TDKDRAH5PS035680
Stock: 27424528
Certified Pre-Owned: No
Showing 484 - 504 out of 2,509 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 2021 Toyota Highlander in Naples, FL Values
Estimated values
2021 Toyota Highlander XSE 4dr SUV (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $31,295 | $33,832 | $36,376 |
| Clean | $30,628 | $33,094 | $35,565 |
| Average | $29,518 | $31,865 | $34,213 |
| Rough | $28,074 | $30,268 | $32,456 |
The average list price of a used 2021 Toyota Highlander in Naples, Florida is $36,307. The average mileage on a used Toyota Highlander 2021 for sale in Naples, Florida is 42,144. Based on the average mileage of 42,144 for used 2021 Toyota Highlander for sale in Naples, FL 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 Naples, Florida to be $29,518.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.