81 Jeep Cherokees for Sale in Winter Park, FL

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2014 Jeep Cherokee Sport

$10,397 72,413 mi. Used
Great Deal
Est. $459 in added features
Drivers Mart
~ 2 mi. away from 32789
(4.7) 416 reviews
  • Exterior Color: Dark Cherry Red Crystal
  • Transmission: 9-Speed Automatic w/OD
  • Drivetrain: FWD
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Seller's Notes: 2014 Jeep Cherokee Sport in Deep Cherry Red Crystal Pearlcoat. Clean A...
Drivers Mart
(4.7) 416 reviews
2 mi. from 32789
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2016 Jeep Cherokee Limited

$22,981 29,085 mi. Used
Good Deal
Est. $7202.93 in added features
Massey Cadillac of Orlando
~ 3 mi. away from 32789
(4.7) 260 reviews
  • Exterior Color: Brilliant Black Crystal Pearlcoat
  • Interior Color: Black
  • Transmission: 9-Speed Automatic
  • Drivetrain: 4WD
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Seller's Notes: This 2016 Jeep Cherokee Limited comes complete with Navigation System,...
Massey Cadillac of Orlando
(4.7) 260 reviews
3 mi. from 32789
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2015 Jeep Cherokee Trailhawk

$24,475 29,038 mi. Used
Great Deal
Est. $10686.71 in added features
Classic Mazda
~ 3 mi. away from 32789
(4.9) 237 reviews
  • Exterior Color: Silver
  • Transmission: Automatic
  • Drivetrain: 4WD
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Seller's Notes: 2015 Jeep Cherokee Trailhawk in Billet Silver Metallic Clearcoat. One ...
Classic Mazda
(4.9) 237 reviews
3 mi. from 32789
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2015 Jeep Cherokee Trailhawk

$23,998 37,844 mi. Used
Great Deal
Est. $8066.76 in added features
Greenway Dodge, Chrysler, Jeep, RAM
~ 5 mi. away from 32789
(4.3) 1853 reviews
  • Exterior Color: Granite Crystal Clearcoat Metallic
  • Transmission: 9-Speed Automatic
  • Drivetrain: 4WD
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Seller's Notes: Chrysler Certified/CPOV. Has sticking power in a storm. Power to the p...
Greenway Dodge, Chrysler, Jeep, RAM
(4.3) 1853 reviews
5 mi. from 32789
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2015 Jeep Cherokee Sport

$14,352 34,097 mi. Used
Great Deal
Est. $424.62 in added features
Greenway Ford
~ 5 mi. away from 32789
(4.7) 2666 reviews
  • Exterior Color: Billet Silver Clearcoat Metallic
  • Interior Color: Black
  • Transmission: 9-Speed Automatic
  • Drivetrain: FWD
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Seller's Notes: ALLOY WHEELS, BACK UP CAMERA, BLUETOOTH, CLEAN CARFAX, and ONE OWNER. ...
Greenway Ford
(4.7) 2666 reviews
5 mi. from 32789
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2015 Jeep Cherokee Latitude

$14,995 47,863 mi. Used
Great Deal
Est. $560.13 in added features
Toyota of Orlando
~ 7 mi. away from 32789
(4.8) 2828 reviews
  • Exterior Color: White
  • Interior Color: Black
  • Transmission: 9-Speed Automatic
  • Drivetrain: FWD
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Seller's Notes: Clean CARFAX. White 2015 Jeep Cherokee Latitude FWD 9-Speed 948TE Auto...
Toyota of Orlando
(4.8) 2828 reviews
7 mi. from 32789
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2015 Jeep Cherokee Latitude

$15,999 20,400 mi. Used
Great Deal
Est. $1347.52 in added features
Airport Chrysler Dodge Jeep RAM
~ 9 mi. away from 32789
(4.7) 184 reviews
  • Exterior Color: Brilliant Black Crystal Pearlcoat
  • Interior Color: Black
  • Transmission: 9-Speed Automatic
  • Drivetrain: FWD
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Seller's Notes: Black 2015 Jeep Cherokee Latitude FWD 9-Speed 948TE Automatic 2.4L 4-C...
Airport Chrysler Dodge Jeep RAM
(4.7) 184 reviews
9 mi. from 32789
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2015 Jeep Cherokee Sport

$15,498 50,407 mi. Used
Good Deal
Est. $581.62 in added features
Sport Auto Group Pre-Owned Sales & Leasing
~ 9 mi. away from 32789
(4.8) 4 reviews
  • Exterior Color: Brilliant Black Crystal Pearlcoat
  • Interior Color: Black
  • Transmission: 9-Speed Automatic
  • Drivetrain: FWD
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Seller's Notes: 2015 Jeep Cherokee - SAVE THOUSANDS with SPORT AUTO GROUP / DON MEALEY...
Sport Auto Group Pre-Owned Sales & Leasing
(4.8) 4 reviews
9 mi. from 32789
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2016 Jeep Cherokee Latitude

$17,999 19,181 mi. Used
Good Deal
Est. $229 in added features
Airport Chrysler Dodge Jeep RAM
~ 9 mi. away from 32789
(4.7) 184 reviews
  • Exterior Color: Deep Cherry Red Crystal Pearlcoat
  • Interior Color: Black
  • Transmission: 9-Speed Automatic
  • Drivetrain: FWD
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Seller's Notes: Deep Cherry Red Crystal 2016 Jeep Cherokee Latitude FWD 9-Speed 948TE ...
Airport Chrysler Dodge Jeep RAM
(4.7) 184 reviews
9 mi. from 32789
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2015 Jeep Cherokee Limited

$21,599 23,321 mi. Used
Good Deal
Est. $5594.61 in added features
CarMax Orlando
~ 9 mi. away from 32789
(3) 5 reviews
  • Exterior Color: Gold
  • Interior Color: Black
  • Transmission: 9-Speed Automatic w/OD
  • Drivetrain: FWD
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Seller's Notes: CarMax makes car buying easy and hassle-free. Our upfront prices are t...
CarMax Orlando
(3) 5 reviews
9 mi. from 32789
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2016 Jeep Cherokee Limited

$18,999 42,525 mi. Used
Good Deal
Est. $4397.16 in added features
RPT Sales & Leasing
~ 10 mi. away from 32789
(3.6) 77 reviews
  • Exterior Color: Brilliant Black Crystal Pearlcoat
  • Interior Color: Black
  • Transmission: 9-Speed Automatic
  • Drivetrain: 4WD
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Seller's Notes: RPT Sales and Leasing is honored to present a wonderful example of pur...
RPT Sales & Leasing
(3.6) 77 reviews
10 mi. from 32789
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2016 Jeep Cherokee Limited

$19,999 18,473 mi. Used
Good Deal
Est. $3845.14 in added features
RPT Sales & Leasing
~ 10 mi. away from 32789
(3.6) 77 reviews
  • Exterior Color: Granite Crystal Clearcoat Metallic
  • Interior Color: Black
  • Transmission: 9-Speed Automatic
  • Drivetrain: FWD
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RPT Sales & Leasing
(3.6) 77 reviews
10 mi. from 32789
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2016 Jeep Cherokee Limited

$18,990 30,152 mi. Used
Good Deal
Est. $6516.72 in added features
Central Florida Chrysler Jeep Dodge RAM
~ 11 mi. away from 32789
(3.9) 241 reviews
  • Exterior Color: White
  • Interior Color: Black
  • Transmission: 9-Speed Automatic
  • Drivetrain: FWD
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Seller's Notes: White Priced below KBB Fair Purchase Price! 4D Sport Utility Clean CAR...
Central Florida Chrysler Jeep Dodge RAM
(3.9) 241 reviews
11 mi. from 32789
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2016 Jeep Cherokee Limited

$19,990 25,267 mi. Used
Good Deal
Est. $6633.57 in added features
Central Florida Chrysler Jeep Dodge RAM
~ 11 mi. away from 32789
(3.9) 241 reviews
  • Exterior Color: Bright White Clearcoat
  • Interior Color: Black
  • Transmission: 9-Speed Automatic
  • Drivetrain: FWD
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Seller's Notes: White Priced below KBB Fair Purchase Price! Odometer is 5228 miles bel...
Central Florida Chrysler Jeep Dodge RAM
(3.9) 241 reviews
11 mi. from 32789
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2014 Jeep Cherokee Sport

$11,685 67,945 mi. Used
Great Deal
Est. $416.74 in added features
David Maus Toyota Scion
~ 13 mi. away from 32789
(4.4) 437 reviews
  • Exterior Color: Black
  • Interior Color: Black
  • Transmission: 9-Speed Automatic
  • Drivetrain: FWD
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Seller's Notes: CARFAX One-Owner. Clean CARFAX. 2014 Jeep Cherokee Sport FWD 9-Speed 9...
David Maus Toyota Scion
(4.4) 437 reviews
13 mi. from 32789
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2017 Jeep Cherokee Latitude

$18,866 6,001 mi. Used
Good Deal
Est. $229 in added features
Fields Chrysler Jeep Dodge RAM
~ 13 mi. away from 32789
(4.7) 259 reviews
  • Exterior Color: Billet Silver Clearcoat Metallic
  • Interior Color: Black
  • Transmission: 9-Speed Automatic
  • Drivetrain: FWD
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Seller's Notes: Bluetooth** Rearview Camera **6 Speaker Audio System **Aux Audio Input...
Fields Chrysler Jeep Dodge RAM
(4.7) 259 reviews
13 mi. from 32789
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2017 Jeep Cherokee Sport

$18,998 8,136 mi. Used
Good Deal
Est. $179 in added features
Fields Chrysler Jeep Dodge RAM
~ 13 mi. away from 32789
(4.7) 259 reviews
  • Exterior Color: Billet Silver Clearcoat Metallic
  • Interior Color: Black
  • Transmission: 9-Speed Automatic
  • Drivetrain: FWD
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Seller's Notes: Bluetooth** Usb Port **5 in Touchscreen Display** 6 Speaker Audio Syst...
Fields Chrysler Jeep Dodge RAM
(4.7) 259 reviews
13 mi. from 32789
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2017 Jeep Cherokee Overland

$32,998 5,060 mi. Used
Fields Chrysler Jeep Dodge RAM
~ 13 mi. away from 32789
(4.7) 259 reviews
  • Exterior Color: Light Brownstone Pearlcoat
  • Interior Color: Brown Pearl
  • Transmission: 9-Speed Automatic
  • Drivetrain: 4WD
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Seller's Notes: Thank you for choosing Fields Auto Group...as part of our unique level...
Fields Chrysler Jeep Dodge RAM
(4.7) 259 reviews
13 mi. from 32789
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2017 Jeep Cherokee Latitude

$16,999 32,464 mi. Used
Good Deal
Est. $229 in added features
Driver's Mart Sanford
~ 14 mi. away from 32789
(3.7) 7 reviews
  • Exterior Color: Black
  • Transmission: 9-Speed Automatic
  • Drivetrain: FWD
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Seller's Notes: Come see this 2017 Jeep Cherokee . Its Automatic transmission and Regu...
Driver's Mart Sanford
(3.7) 7 reviews
14 mi. from 32789
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2015 Jeep Cherokee Limited

$19,250 68,140 mi. Used
Good Deal
Est. $4498.95 in added features
Napleton Chrysler Jeep Dodge RAM
~ 17 mi. away from 32789
(4.8) 735 reviews
  • Exterior Color: Brilliant Black Crystal Pearlcoat
  • Interior Color: Black
  • Transmission: 9-Speed Automatic
  • Drivetrain: 4WD
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Seller's Notes: 2015 Jeep Cherokee Limited Brilliant Black Crystal Pearlcoat, *4X4*, *...
Napleton Chrysler Jeep Dodge RAM
(4.8) 735 reviews
17 mi. from 32789
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2016 Jeep Cherokee Sport

$16,383 20,298 mi. Used
Good Deal
Est. $652 in added features
Napleton Chrysler Jeep Dodge RAM
~ 17 mi. away from 32789
(4.8) 735 reviews
  • Exterior Color: Brilliant Black Crystal Pearlcoat
  • Interior Color: Black
  • Transmission: 9-Speed Automatic
  • Drivetrain: FWD
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Seller's Notes: 2016 Jeep Cherokee Sport Black, *AUTOMATIC*, *SPORT PACKAGE*, *JEEP CE...
Napleton Chrysler Jeep Dodge RAM
(4.8) 735 reviews
17 mi. from 32789
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2016 Jeep Cherokee Limited

$19,451 41,417 mi. Used
Good Deal
Est. $3701.64 in added features
Napleton Chrysler Jeep Dodge RAM
~ 17 mi. away from 32789
(4.8) 735 reviews
  • Exterior Color: Black
  • Interior Color: Black
  • Transmission: 9-Speed Automatic
  • Drivetrain: 4WD
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Seller's Notes: 2016 Jeep Cherokee Limited Black, *LIMITED PACKAGE*, *JEEP CERTIFIED I...
Napleton Chrysler Jeep Dodge RAM
(4.8) 735 reviews
17 mi. from 32789
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2014 Jeep Cherokee Limited

$18,733 28,733 mi. Used
Good Deal
Est. $4029.7 in added features
Napleton Clermont Chrysler Jeep Dodge RAM
~ 20 mi. away from 32789
(4.8) 742 reviews
  • Exterior Color: Granite Crystal Clearcoat Metallic
  • Interior Color: Black / Iceland Gray
  • Transmission: 9-Speed Automatic
  • Drivetrain: FWD
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Seller's Notes: *ALLOY WHEELS*, *CLEAN ONE OWNER CARFAX*, *FUEL EFFICIENT*, *HEATED LE...
Napleton Clermont Chrysler Jeep Dodge RAM
(4.8) 742 reviews
20 mi. from 32789
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2017 Jeep Cherokee Sport

$18,997 1,068 mi. Used
Good Deal
Est. $179 in added features
DeLand Hurley Chrysler Jeep Dodge Ram
~ 27 mi. away from 32789
(4.8) 286 reviews
  • Exterior Color: Deep Cherry Red Crystal Pearlcoat
  • Interior Color: Black
  • Transmission: 9-Speed Automatic
  • Drivetrain: FWD
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Seller's Notes: *REMAINDER OF FACTORY WARRANTY*, *CARFAX ONE OWNER...NO ACCIDENTS*, *B...
DeLand Hurley Chrysler Jeep Dodge Ram
(4.8) 286 reviews
27 mi. from 32789
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2017 Jeep Cherokee Latitude

$18,594 4,486 mi. Used
Great Deal
Est. $229 in added features
DeLand Hurley Chrysler Jeep Dodge Ram
~ 27 mi. away from 32789
(4.8) 286 reviews
  • Exterior Color: Light Brownstone Pearlcoat
  • Interior Color: Black
  • Transmission: 9-Speed Automatic
  • Drivetrain: FWD
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Seller's Notes: *CARFAX ONE OWNER...NO ACCIDENTS*, *BOUGHT HERE NEW, WE HAVE ALL RECOR...
DeLand Hurley Chrysler Jeep Dodge Ram
(4.8) 286 reviews
27 mi. from 32789
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2015 Jeep Cherokee Sport

$14,200 40,763 mi. Used
Good Deal
Est. $179 in added features
RC Hill Mitsubishi
~ 27 mi. away from 32789
(4.9) 1781 reviews
  • Exterior Color: Bright White Clearcoat
  • Interior Color: Black
  • Transmission: 9-Speed Automatic
  • Drivetrain: FWD
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Seller's Notes: LIFETIME LIMITED WARRANTY, ** look at this ONE OWNER, ** FLORIDA CAR, ...
RC Hill Mitsubishi
(4.9) 1781 reviews
27 mi. from 32789
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2015 Jeep Cherokee Limited

$21,250 47,120 mi. Used
Good Deal
Est. $6430.57 in added features
Carvana Orlando (As Soon as Next Day Delivery)
~ 4 mi. away from 32789
(5) 12 reviews
  • Exterior Color: True Blue Pearlcoat
  • Interior Color: Black / Light Frost Beige
  • Transmission: 9-Speed Automatic
  • Drivetrain: 4WD
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Seller's Notes: Can't get your mind off a 2015JeepCherokee with 24.6 cu. ft. of cargo ...
Carvana Orlando (As Soon as Next Day Delivery)
(5) 12 reviews
4 mi. from 32789
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2017 Jeep Cherokee Latitude

$16,999 37,426 mi. Used
Good Deal
Est. $2163.84 in added features
Off Lease Only Orlando
~ 11 mi. away from 32789
(4.9) 8930 reviews
  • Exterior Color: Deep Cherry Red Crystal Pearlcoat
  • Interior Color: Black
  • Transmission: 9-Speed Automatic w/OD
  • Drivetrain: 4WD
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Seller's Notes: NO DEALER FEES! The Nation's Used Car Destination! Thousands of Cars ...
Off Lease Only Orlando
(4.9) 8930 reviews
11 mi. from 32789
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2017 Jeep Cherokee Limited

$17,999 30,530 mi. Used
Good Deal
Est. $5219.34 in added features
Off Lease Only Orlando
~ 11 mi. away from 32789
(4.9) 8930 reviews
  • Exterior Color: Granite Crystal Metallic Clearcoat
  • Interior Color: Black
  • Transmission: 9-Speed Automatic w/OD
  • Drivetrain: FWD
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Seller's Notes: NO DEALER FEES! THIS VEHICLE IS PRICED $2,536 BELOW THE MARKET AVERAGE...
Off Lease Only Orlando
(4.9) 8930 reviews
11 mi. from 32789
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2016 Jeep Cherokee Sport Altitude 4dr SUV

$18,480 15,873 mi. Used
Good Deal
Est. $356 in added features
VROOM (Orlando)
~ 4 mi. away from 32789
(2.9) 253 reviews
  • Exterior Color: White
  • Interior Color: Black
  • Transmission: 9-Speed Automatic w/OD
  • Drivetrain: FWD
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Seller's Notes: Altitude Package, 2.4L I4 MPI Engine, Automatic Transmission, Cloth Se...
VROOM (Orlando)
(2.9) 253 reviews
4 mi. from 32789
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