Cruiser Motorcycles For Sale near Milwaukee, WI

Red 2022 Harley-Davidson® FLHCS Heritage Classic 114 motorcycleCruiser motorcycles are designed for those who appreciate style and comfort on the open road. At Road Track & Trail we feature a wide range of cruiser motorcycles for sale that cater to all types of riders. We are proud to be your local cruiser motorcycle dealer serving Milwaukee, WI! Contact us today to find your perfect ride!
$9,799.00
Price Drop Alert
ONLY 15,001 MILES, 1-OWNER, KEYLESS START, ABS, TRACTION CONTROL, CRUISE CONTROL, RIDE MODES CONTROL, BLUETOOTH, ON-BOARD COMPUTER, LED HEADLIGHT, LED SIGNALS, BAR END MIRRORS, NEW TIRES, AND MORE! CLEAN FACTORY LOADED BLACKED OUT SPORTSTER CRUISER!
  • Mileage15,001
  • Stock312897
  • ConditionPreOwned
  • ColorGray
$7,899.00
Price Drop Alert
ONLY 5289 MILES, 1-OWNER, PASSENGER SEAT AND PEGS, KEYLESS START, SECURITY, ABS, TRACTION CONTROL, CRUISE CONTROL, BLUETOOTH, RIDE MODES CONTROL, ON-BOARD COMPUTER, BAR END MIRRORS, AND MORE! STOCK AND CLEAN NEW STYLE BLACKED OUT CRUISER!
  • Mileage5,289
  • Stock317111
  • ConditionPreOwned
  • ColorBLACK DENIM
$7,899.00
Price Drop Alert
ONLY 1044 MILES, 1-OWNER, ABS MODEL, FREEDOM PERFORMANCE EXHAUST, PASSENGER SEAT AND PEGS, BACKREST, PHONE MOUNT, AND FUEL INJECTED! SUPER CLEAN AND LOADED LOW MILEAGE CHOPPER STYLE CRUISER!
  • Mileage1,044
  • Stock700568
  • ConditionPreOwned
  • ColorYELLOW
$6,299.00
Price Drop Alert
ONLY 3804 MILES, 1-OWNER, LED HEADLIGHT, CRASHBAR, HWY PEGS, FOG LIGHTS, AND FUEL INJECTED! SUPER CLEAN LOW MILEAGE BLACKED OUT CRUISER!
  • Mileage3,804
  • Stock300485
  • ConditionPreOwned
  • ColorMATTE BLACK
get inventory updates
$8,899.00
Price Drop Alert
ONLY 1799 MILES, 1-OWNER, FACTORY WARRANTY THROUGH 9/7/2025, TAB PERFORMANCE EXHAUST, UPGRADED BIGGER HANDLEBARS, RIDER FLOORBOARDS, UPGRADED MIRRORS, LED SIGNALS, AND MORE! CLEAN AND LOADED LOW MILEAGE BLACKED OUT CRUISER!
  • Mileage1,799
  • Stock196234
  • ConditionPreOwned
  • ColorBLACK
$15,399.00
Price Drop Alert
ONLY 2565 MILES, 1-OWNER, FACTORY WARRANTY THROUGH 8/22/2025, AND EXTENDED SERVICE CONTRACT THROUGH 8/22/2026! $1500 SAWICKI SPEED 2 INTO 1 EXHAUST, INDIAN UPGRADED HIGH FLOW INTAKE, SADDLEMEN STEP UP SEAT, INDIAN LED HEADLIGHT, LED SIGNALS, REAR FOX RESERVOIR SHOCKS, NAVIGATION, BLUETOOTH, ABS, TRACTION CONTROL, CRUISE CONTROL, RIDE MODES CONTROL, ON-BOARD COMPUTER, 116" MOTOR, 6 SPEED TRANS, AND MORE! CRISPY CLEAN AND LOADED BLACKED OUT MUSCLE CRUISER! SWEET SOUND!
  • Mileage2,565
  • Stock012122
  • ConditionPreOwned
  • ColorGRAY
$15,399.00
Price Drop Alert
ONLY 3476 MILES, FACTORY WARRANTY TRHOUGH 9/5/2025! RINEHART EXHAUST, INDIAN UPGRADED HIGH FLOW INTAKE, FOX REAR RESERVOIR SHOCKS, INDIAN LED HEADLIGHT, LED SIGNALS, NAVIGATION, BLUETOOTH, ABS, TRACTION CONTROL, CRUISE CONTROL, RIDE MODES CONTROL, ON-BOARD COMPUTER, KEYLESS START, 116" MOTOR, 6 SPEED TRANSMISSION, HEADLIGHT FAIRING, AND MORE! CRISPY CLEAN AND LOADED BLACKED OUT MUSCLE CRUISER!
  • Mileage3,476
  • Stock013224
  • ConditionPreOwned
  • ColorGRAY
$5,899.00
Price Drop Alert
ONLY 1363 MILES, 1-OWNER, AFTERMARKET HEAT WRAPPED EXHAUST, AFTERMARKET LED SIGNALS, REAR TAIL TIDY, AND FUEL INJECTED! CLEAN LOW MILEAGE BLACKED OUT CRUISER! THE RIGHT SIDE OF THE GAS TANK HAS A SCRATCH THAT IS TOURCHED UP.
  • Mileage1,363
  • Stock000219
  • ConditionPreOwned
  • ColorGREEN/BLACK
$9,899.00
Price Drop Alert
ONLY 1240 MILES, 1-OWNER, UPGRADED BEACH BAR STYLE HANDLEBARS, MUSTANG BROWN SEAT WITH RIDERS BACKREST, SADDLEBAGS, WINDSHIELD, ROLAND SANDS DESIGN ENGINE COVERS, KEYLESS RIDE, ABS, TRACTION CONTROL, CRUISE CONTROL, RIDER MINI FLOORBOARDS, LIGHTBAR, BMW LED HEADLIGHT, LED SIGNALS, BMW MOTORRAD EXHAUST TIPS, AND MORE! CLEAN AND LOADED RETRO CRUISER!
  • Mileage1,240
  • StockF22076
  • ConditionPreOwned
  • ColorBLACK STORM METALLIC
get inventory updates
$4,899.00
Price Drop Alert
ONLY 13,186 MILES, 1-OWNER, 21" BLACK SPOKE FRONT WHEEL, AFTERMARKET HEAT WRAPPED EXHAUST, UPGRADED HANDLEBARS, HEADLIGHT FAIRING, LED HEADLIGHT, LED SIGNALS, AFTERMARKET QUILTED 2-UP SEAT, MOTO STYLE RIDER PEGS, SISSY BAR AND RACK, LICENSE PLATE RELOCATION KIT, UPGRADED GRIPS, HD EMULSION SHOCKS, FUEL INJECTED, AND NEW REAR TIRE! NICE AND LOADED BLACKED OUT SPORTSTER CRUISER! THE GAS TANK HAS A COUPLE DINGS AND SCRATCHES.
  • Mileage13,186
  • Stock410762
  • ConditionPreOwned
  • ColorDENIM BLACK
$7,399.00
Price Drop Alert
ONLY 1508 MILES, 1-OWNER, TWO BROTHERS RACING EXHAUST, PUIG WINDSHIELD, CORBIN SOLO SEAT, UPGRADED HANDLEBARS, DUAL CLUTCH TRANSMISSION WITH AUTOMATIC OR PUSH BUTTON SHIFT, UPGRADED RIDER PEGS, REAR RESERVOIR SHOCKS, ABS, TRACTION CONTROL, CRUISE CONTROL, RIDE MODES CONTROL, LED HEADLIGHT, LED SIGNALS AND MORE! CRISPY CLEAN AND LOADED BLACKED OUT CRUISER!
  • Mileage1,508
  • Stock100364
  • ConditionPreOwned
  • ColorBLACK
$13,399.00
Price Drop Alert
WOW FACTOR! ONLY 6051 MILES, 116" MOTOR, TAB PERFORMANCE EXHAUST, INDIAN UPGRADED HIGH FLOW INTAKE, INDIAN SADDLEBAGS, MUSTANG QUILTED TOURING SEATS, INDIAN BACKREST, INDIAN WINDSHIELD, INDIAN LED HEADLIGHT, INDIAN LED SPOT LIGHTS, LED SIGNALS, CRASHBAR, HWY PEGS, PASSENGER PEGS, UPGRADED HANDLEBARS, RAM PHONE MOUNT, KEYLESS START, NAVIGATION, BLUETOOTH, TOUCH SCREEN, CRUISE CONTROL, RIDE MODES CONTROL, ABS, TRACTION CONTROL, ON-BOARD COMPUTER, 6 SPEED TRANS, AND MORE! SUPER CLEAN AND LOADED BLACKED OUT BIG MOTOR CRUISER! TONS OF BIG MONEY EXTRAS!
  • Mileage6,051
  • Stock000278
  • ConditionPreOwned
  • ColorBLACK SMOKE
$10,499.00
Price Drop Alert
ONLY 5,915 MILES, 1-OWNER, DEAN SPEED EXHAUST, LLOYDZ WORKS HIGH FLOW INTAKE, THUNDERSTROKE STAGE II PERFROMANCE CAMS AND TUNE, UPGRADED BIG HANDLEBARS, INDIAN UPGRADED GRIPS AND FOOT CONTROLS, CONTRAST CUT ADJUSTABLE LEVERS, INDIAN LED HEADLIGHT, LED SIGNALS, RIDER FLOORBOARDS, KEYLESS START, CRUISE CONTROL, SECURITY, 111" MOTOR, AND 6 SPEED TRANS! CLEAN AND COOL BLACKED OUT BOBBER CRUISER!
  • Mileage5,915
  • Stock002627
  • ConditionPreOwned
  • ColorBLACK
$15,999.00
Price Drop Alert
ONLY 3677 MILES, 1-OWNER, UPGRADED INDIAN EXHAUST, UPGRADED INDIAN HIGH FLOW INTAKE, UPGRADED HANDLEBARS, CRASHBAR, WINDSHIELD, INDIAN LED HEADLIGHT, LED SIGNALS, LED TAIL LIGHT, CHROME FENDER TRIM, KEYLESS START, SECURITY, ABS, CRUISE CONTROL, RIDE MODES CONTROL, CENTRAL LOCKING, 111" MOTOR, 6 SPEED TRANS, AND DRESSED IN FACTORY CHROME! CLEAN AND LOADED 2-TONE CLASSIC BAGGER!
  • Mileage3,677
  • Stock407034
  • ConditionPreOwned
  • ColorBLACK/TAN
get inventory updates
$6,599.00
Price Drop Alert
ONLY 4968 MILES, 1-OWNER, FUEL INJECTED, STOCK AND CLEAN BLACKED OUT CRUISER! NFS.
  • Mileage4,968
  • Stock078243
  • ConditionPreOwned
  • ColorTEAL/GRAY