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74 listings
  • $24,908
    fair price
    $823 below market
    • 50,821 miles
    • No accidents, 1 owner, rental vehicle
    • 5 Seats, 19 City / 26 Hwy MPG
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in West Palm Beach, FL / 153 miles away from Windermere, 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:

    21 Combined MPG (19 City/26 Highway)

    Listing Information:

    VIN: 1C4RJEBG4NC125875
    Stock: 7VPJDL
    Certified Pre-Owned: No
    Listed since: 07-10-2025

  • $26,990
    fair price
    $271 above market
    • 36,398 miles
    • No accidents, 1 owner, personal use only
    • 5 Seats, 19 City / 26 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    • Blind Spot Monitorin...
    Close

    Located in Atlanta, GA / 404 miles away from Windermere, 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: Yes

    Features and Specs:

    21 Combined MPG (19 City/26 Highway)

    Listing Information:

    VIN: 1C4RJEAG8NC154264
    Stock: 2003923426
    Certified Pre-Owned: No
    Listed since: 07-24-2025

  • Price Drop
    $28,990
    fair price
    $385 above market
    • 35,874 miles
    • No accidents, 2 owners, personal use
    • 5 Seats, 18 City / 25 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Oklahoma City, OK / 1,051 miles away from Windermere, 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:

    21 Combined MPG (18 City/25 Highway)

    Listing Information:

    VIN: 1C4RJFAG5NC118683
    Stock: 2003872435
    Certified Pre-Owned: No
    Listed since: 07-09-2025

  • New Listing
    $26,990
    fair price
    $303 above market
    • 42,303 miles
    • No accidents, 1 owner, personal use only
    • 5 Seats, 19 City / 26 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Chicago, IL / 1,015 miles away from Windermere, 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:

    21 Combined MPG (19 City/26 Highway)

    Listing Information:

    VIN: 1C4RJEBGXNC128442
    Stock: 2003874337
    Certified Pre-Owned: No
    Listed since: 07-19-2025

  • New Listing
    $26,058
    fair price
    $560 below market
    • 51,576 miles
    • 5 Seats, 18 City / 25 Hwy MPG
    • Jarrett Ford (41 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Dade City, FL / 41 miles away from Windermere, FL

    AutoCheck Vehicle History Summary Unavailable.

    Features and Specs:

    21 Combined MPG (18 City/25 Highway)

    Listing Information:

    VIN: 1C4RJFBG8NC111077
    Stock: P11935
    Certified Pre-Owned: No
    Listed since: 03-11-2025

    • 47,708 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 5 Seats, 18 City / 25 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Dallas, TX / 952 miles away from Windermere, 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: 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:

    21 Combined MPG (18 City/25 Highway)

    Listing Information:

    VIN: 1C4RJFBG0NC145014
    Stock: 2003904363
    Certified Pre-Owned: No
    Listed since: 07-21-2025

  • New Listing
    $29,998
    good price
    $1,113 below market
    • 48,050 miles
    • 5 Seats, 18 City / 25 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from GA to FL*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Norcross, GA / 406 miles away from Windermere, 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:

    21 Combined MPG (18 City/25 Highway)

    Listing Information:

    VIN: 1C4RJFBG5NC141458
    Stock: 27609202
    Certified Pre-Owned: No

  • New Listing
    • 60,380 miles
    • No accidents, 2 owners, personal use only
    • 5 Seats, 18 City / 25 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Indianapolis, IN / 823 miles away from Windermere, 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:

    21 Combined MPG (18 City/25 Highway)

    Listing Information:

    VIN: 1C4RJFAG5NC120479
    Stock: 2003926412
    Certified Pre-Owned: No
    Listed since: 07-30-2025

  • New Listing
    $28,998
    fair price
    $79 above market
    • 38,984 miles
    • 5 Seats, 18 City / 25 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from WI to FL*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Waukesha, WI / 1,070 miles away from Windermere, 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:

    21 Combined MPG (18 City/25 Highway)

    Listing Information:

    VIN: 1C4RJFBG5NC144232
    Stock: 27107055
    Certified Pre-Owned: No

  • Price Drop
    Stock photo**
    $26,087
    good price
    $1,378 below market
    • 56,564 miles
    • 1 accident, 1 owner, personal use
    • 5 Seats, 18 City / 25 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Sunroof/Moonroof
    Close

    Located in Hamilton, NJ / 900 miles away from Windermere, FL

    CarFax 1-Owner,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,Navigation System,Remote Star...

    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:

    21 Combined MPG (18 City/25 Highway)

    Listing Information:

    VIN: 1C4RJFAG6NC115193
    Stock: NC115193U
    Certified Pre-Owned: No

  • New Listing
    • 25,945 miles
    • 1 accident, 1 owner, corporate fleet vehicle
    • 5 Seats, 18 City / 25 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Dallas, TX / 952 miles away from Windermere, 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: 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:

    21 Combined MPG (18 City/25 Highway)

    Listing Information:

    VIN: 1C4RJFBG0NC145451
    Stock: 2003923297
    Certified Pre-Owned: No
    Listed since: 07-24-2025

  • New Listing
    • 63,337 miles
    • 1 accident, 2 owners, personal use only
    • 5 Seats, 19 City / 26 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Abilene, TX / 1,121 miles away from Windermere, FL

    High Demand,Rare Find,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,Leather Seats,Navigati...

    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:

    21 Combined MPG (19 City/26 Highway)

    Listing Information:

    VIN: 1C4RJEBG5NC128154
    Stock: 38869T
    Certified Pre-Owned: No

  • New Listing
    $25,998
    fair price
    $668 above market
    • 41,489 miles
    • 5 Seats, 19 City / 26 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from TN to FL*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    • Blind Spot Monitorin...
    Close

    Located in Chattanooga, TN / 499 miles away from Windermere, 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:

    21 Combined MPG (19 City/26 Highway)

    Listing Information:

    VIN: 1C4RJEAG5NC155971
    Stock: 27634795
    Certified Pre-Owned: No

  • New Listing
    $26,499
    fair price
    $186 below market
    • 35,060 miles
    • 5 Seats, 18 City / 25 Hwy MPG
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Huntington, NY / 969 miles away from Windermere, 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 Unavailable.

    Features and Specs:

    21 Combined MPG (18 City/25 Highway)

    Listing Information:

    VIN: 1C4RJFAG2NC175682
    Stock: 8GJN8R
    Certified Pre-Owned: No
    Listed since: 07-23-2025

    • 75,436 miles
    • No accidents, 1 owner, personal use
    • 5 Seats, 19 City / 26 Hwy MPG
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Tulsa, OK / 988 miles away from Windermere, 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:

    21 Combined MPG (19 City/26 Highway)

    Listing Information:

    VIN: 1C4RJEBG6NC156013
    Stock: 8GH1RM
    Certified Pre-Owned: No
    Listed since: 06-20-2025

    • 45,126 miles
    • 1 accident, 1 owner, corporate fleet vehicle
    • 5 Seats, 18 City / 25 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Indianapolis, IN / 823 miles away from Windermere, 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: 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:

    21 Combined MPG (18 City/25 Highway)

    Listing Information:

    VIN: 1C4RJFBG3NC166245
    Stock: 2003867738
    Certified Pre-Owned: No
    Listed since: 07-09-2025

  • $26,998
    fair price
    $98 below market
    • 56,716 miles
    • 1 accident, 1 owner, personal use
    • 5 Seats, 18 City / 25 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from MD to FL*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Brandywine, MD / 752 miles away from Windermere, 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: 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:

    21 Combined MPG (18 City/25 Highway)

    Listing Information:

    VIN: 1C4RJFBG9NC121455
    Stock: 27525292
    Certified Pre-Owned: No

  • Price Drop
    • 22,047 miles
    • No accidents, 1 owner, personal use only
    • 5 Seats, 18 City / 25 Hwy MPG
    • Bartow Ford (44 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Bartow, FL / 44 miles away from Windermere, FL

    THIS IS A LOW MILEAGE 4X4 ONE OWNER TRADE IN, IT HAS THE UPGRADED WK LAREDO X PACKAGE, THE OPTIONAL SUEDE SEATS, V6 ENGINE, THE CUSTOMER PREFERRED PAC...

    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:

    21 Combined MPG (18 City/25 Highway)

    Listing Information:

    VIN: 1C4RJFAG0NC122673
    Stock: D1997B
    Certified Pre-Owned: No
    Listed since: 07-02-2025

    • 82,840 miles
    • No accidents, 1 owner, personal use only
    • 5 Seats, 19 City / 26 Hwy MPG
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Houston, TX / 828 miles away from Windermere, 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:

    21 Combined MPG (19 City/26 Highway)

    Listing Information:

    VIN: 1C4RJEBG4NC156012
    Stock: 8GJ5HH
    Certified Pre-Owned: No
    Listed since: 06-23-2025

    • 30,446 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 5 Seats, 19 City / 26 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    • Blind Spot Monitorin...
    Close

    Located in Charlotte, NC / 466 miles away from Windermere, 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: 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:

    21 Combined MPG (19 City/26 Highway)

    Listing Information:

    VIN: 1C4RJEAG0NC172757
    Stock: 2003747831
    Certified Pre-Owned: No
    Listed since: 05-17-2025

    • 31,944 miles
    • No accidents, 1 owner, personal use
    • 5 Seats, 18 City / 25 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from TX to FL*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Lubbock, TX / 1,256 miles away from Windermere, 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:

    21 Combined MPG (18 City/25 Highway)

    Listing Information:

    VIN: 1C4RJFBG8NC165916
    Stock: 27520880
    Certified Pre-Owned: No

Showing 43 - 63 out of 74 listings

Buying a Jeep Grand Cherokee WK in Windermere Florida

The Jeep Grand Cherokee WK stands out as an ideal choice for residents of Windermere, FL, especially those who enjoy outdoor adventures. Its impressive off-roading capabilities make it well-suited for tackling nearby nature trails, lakes, and parks. Whether heading to a weekend escape in the great outdoors or navigating local dirt roads, this SUV is built to confidently handle rough terrain. Additionally, its substantial towing capacity allows for easy transport of boats or camping gear, perfect for enjoying Windermere’s beautiful lakes and waterways.

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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.