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2,523 listings
- $29,987good price$1,281 below market
- 59,343 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- Driveway (155 mi away)
- Home delivery*
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Located in New Port Richey, FL / 155 miles away from Naples, FL
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 - Price Drop$32,500good price$1,764 below market
- 26,529 miles
- No accidents, 1 owner, personal use
- 8 Seats, 22 City / 29 Hwy MPG
- Lexus of Winter Park (169 mi away)
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Located in Winter Park, FL / 169 miles away from Naples, FL
JUST TRADED IN, 1 OWNER & SPOTLESS CARFAX HISTORY, LE PACKAGE, 18" ALLOY WHEELS, POWER LIFTGATE, WIRELESS APPLE CARPLAY & ANDROID AUTO, DEALER SERVICE...
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: 5TDKDRAH3PS033992
Stock: PS033992
Certified Pre-Owned: No
Listed since: 05-04-2025 - New Listing$40,998good price
- 25,463 miles
- No accidents, 1 owner, personal use
- 7 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to FL*
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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: 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: 5TDKDRAH7PS040010
Stock: 27295522
Certified Pre-Owned: No - $35,495fair price$152 above market
- 13,118 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- West Kendall Toyota (89 mi away)
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Located in Miami, FL / 89 miles away from Naples, FL
Certified. Rear Back Up Camera, LOW Miles, NonSmoker, iphone / Droid Navigation Compatible, Bluetooth, GREAT VALUE!, ECONOMY CAR!, Gas Saving!, Great ...
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: 5TDKDRAH2PS038861
Stock: W411397A
Certified Pre-Owned: Yes
Listed since: 05-03-2025 - Price Drop$42,998fair price$689 below market
- 20,481 miles
- No accidents, 1 owner, personal use only
- 8 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from SC to FL*
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Located in Greenville, SC / 597 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: 5TDKDRAH8PS520248
Stock: 27446252
Certified Pre-Owned: No - Price Drop$30,941fair price$901 below market
- 47,074 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Coggin Chevrolet at the Avenues (276 mi away)
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Located in Jacksonville, FL / 276 miles away from Naples, FL
RECALL NOTICE: Some vehicles offered for sale may be subject to unrepaired manufacturer safety recalls. To determine the recall status of a vehicle, v...
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: 5TDKDRAH0PS500379
Stock: CCAQ231172
Certified Pre-Owned: No
Listed since: 04-12-2025 - New Listing$33,000fair price$396 below market
- 36,917 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Firkins Chrysler Dodge Jeep Ram (104 mi away)
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Located in Bradenton, FL / 104 miles away from Naples, FL
CARFAX One-Owner. Magnetic Gray Metallic 2023 Toyota Highlander L FWD FWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp ***LO...
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: 5TDKDRAHXPS027610
Stock: U4025P
Certified Pre-Owned: No
Listed since: 12-13-2024 - New Listing$33,499fair price$572 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 - New Listing$31,998fair price$1,025 below market
- 48,674 miles
- No accidents, 2 owners, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from NC to FL*
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Located in Pineville, NC / 618 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: 5TDKDRAH5PS014165
Stock: 27282020
Certified Pre-Owned: No - New Listing$33,889fair price$494 below market
- 52,178 miles
- No accidents, 2 owners, personal use
- 7 Seats, 21 City / 29 Hwy MPG
- Sport Subaru South (155 mi away)
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Located in Orlando, FL / 155 miles away from Naples, FL
Rev up your life with this sleek and reliable ride - your ticket to endless adventures awaits!!! Sport Auto Group's ONE PRICE means you NEVER PAY too ...
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: 5TDYZRAHXMS055916
Stock: BT055916
Certified Pre-Owned: No
Listed since: 05-19-2025 - $38,599fair price$356 below market
- 39,484 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Redwood City, CA / 2,482 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: 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: 5TDKDRBH5PS030980
Stock: 7W2PXT
Certified Pre-Owned: No
Listed since: 04-08-2025 - $31,392good price$2,021 below market
- 30,952 miles
- 1 accident, 1 owner, personal use
- 8 Seats, 22 City / 29 Hwy MPG
- Honda of Ocala (209 mi away)
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Located in Ocala, FL / 209 miles away from Naples, FL
!!! Lifetime Powertrain Warranty !!! This is a one owner vehicle with a clean CARFAX report. It comes equipped with automatic transmission, power wind...
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: 5TDKDRAH6PS045361
Stock: 045361
Certified Pre-Owned: No
Listed since: 04-01-2025 - $33,991fair price$781 below market
- 41,662 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Miracle Toyota (135 mi away)
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Located in Haines City, FL / 135 miles away from Naples, FL
Certified CARFAX One-Owner. Clean CARFAX. Miracle Toyota is pumped up to offer this terrific-looking 2023 Toyota Highlander in Midnight Black Metallic...
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: 5TDKDRAH7PS032862
Stock: PPS032862
Certified Pre-Owned: No
Listed since: 04-12-2025 - Price Drop$32,998fair price$565 below market
- 35,370 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 21 City / 29 Hwy MPG
- CarMax Sanford (182 mi away)
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Located in Sanford, FL / 182 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: 5TDGZRAH5MS080959
Stock: 27066031
Certified Pre-Owned: No - $31,396fair price$671 below market
- 41,174 miles
- No accidents, 1 owner, rental vehicle
- 8 Seats, 22 City / 29 Hwy MPG
- Paul Clark Ford (307 mi away)
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Located in Yulee, FL / 307 miles away from Naples, FL
Bluetooth HANDS FREE PHONE, BACK UP CAMERA, 3RD ROW SEATING, ONE OWNER, CLEAN CARFAX - NO ACCIDENT, LOW LOW MILES !. Gray 2023 Toyota Highlander LE ...
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: 5TDKDRAH8PS015889
Stock: PC2837
Certified Pre-Owned: No
Listed since: 02-21-2025 - $36,997good price$2,297 below market
- 37,627 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Schumacher Chevrolet of North Palm Beach (109 mi away)
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Located in Lake Park, FL / 109 miles away from Naples, FL
White 2023 Toyota Highlander XLE FWD 8-Speed Automatic 2.4L I4 PDI Turbocharged DOHC 16V LEV3-SULEV30 265hp ABS brakes, Active Cruise Control, Alloy w...
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: 5TDKDRAH6PS039379
Stock: V240350M
Certified Pre-Owned: No
Listed since: 04-30-2025 - New Listing$36,998good price$1,633 below market
- 44,252 miles
- No accidents, 1 owner, rental vehicle
- 7 Seats, 21 City / 28 Hwy MPG
- CarMax (In-stock online)
- Transfer available from VA to FL*
Close
Located in Newport News, VA / 817 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:
24 Combined MPG (21 City/28 Highway)
Listing Information:
VIN: 5TDKDRBH3PS500746
Stock: 27054969
Certified Pre-Owned: No - $29,376good price$1,118 below market
- 84,637 miles
- No accidents, 2 owners, personal use only
- 7 Seats, 20 City / 27 Hwy MPG
- Audi Hilton Head (426 mi away)
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Located in Hardeeville, SC / 426 miles away from Naples, FL
Sun/Moonroof3rd Row SeatLane Keeping AssistKeyless StartRear Spoiler50 State EmissionsBlack; Softex Seat TrimMagnetic Gray Metallic#Excellen...
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: 5TDGZRBH8MS531400
Stock: MS531400
Certified Pre-Owned: No
Listed since: 04-24-2025 - $39,494good price$1,496 below market
- 34,962 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 21 City / 28 Hwy MPG
- INFINITI of Mobile (498 mi away)
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Located in Mobile, AL / 498 miles away from Naples, FL
Recent Arrival! New Price! XLE Odometer is 4458 miles below market average! Active Park Assist, Automatic Headlights, Backup Camera, Blind Spot Monito...
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: 5TDKDRBH0PS527175
Stock: I27175B
Certified Pre-Owned: No
Listed since: 03-28-2025 - Price Drop$39,591good price$1,106 below market
- 50,695 miles
- No accidents, 1 owner, personal use only
- 7 Seats, 22 City / 29 Hwy MPG
- Miracle Toyota (135 mi away)
Close
Located in Haines City, FL / 135 miles away from Naples, FL
Certified. CARFAX One-Owner. Clean CARFAX. ABS brakes, Active Cruise Control, Alloy wheels, Electronic Stability Control, Front dual zone A/C, Heated ...
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: 5TDKDRAH8PS029811
Stock: PS029811
Certified Pre-Owned: No
Listed since: 04-15-2025 - $33,998fair price
- 28,833 miles
- No accidents, 1 owner, personal use
- 8 Seats, 22 City / 29 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to FL*
Close
Located in Fort Worth, TX / 1,044 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: 5TDKDRAH6PS011632
Stock: 26753642
Certified Pre-Owned: No
Showing 400 - 420 out of 2,523 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 XLE 4dr SUV (3.5L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $29,408 | $31,667 | $33,931 |
| Clean | $28,782 | $30,977 | $33,175 |
| Average | $27,739 | $29,826 | $31,914 |
| Rough | $26,382 | $28,331 | $30,275 |
The average list price of a used 2021 Toyota Highlander in Naples, Florida is $34,768. The average mileage on a used Toyota Highlander 2021 for sale in Naples, Florida is 40,182. Based on the average mileage of 40,182 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 $27,739.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.