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Used Harley-Davidson HERITAGE SOFTAIL Motorcycles for Sale in elgin, Illinois

Looking to buy a Harley-Davidson Heritage Softail motorcycle in Elgin, Illinois? Browse our extensive inventory of new and used Harley-Davidson Heritage Softail motorcycles from local Harley-Davidson dealers and private sellers in Elgin, Illinois. Compare prices, models, trims, options and specifications between different Harley-Davidson motorcycles on Cycle Trader.
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225 Used Harley-Davidson HERITAGE SOFTAIL Motorcycles For Sale

2020 Harley-Davidson Heritage Classic 114 CLASSIC in Wauconda, IL
$11,999

Used 2020 Harley-Davidson Cruiser

Heritage Classic 114 CLASSIC
Stock # AC4545
<p>Windshield, Light Bar Kit and Cobra Pipes!</p><p style="margin-bottom: 1em;">The refined finishes, modern edge and reinvigorated ride of the Heritage model take nostalgia ripping into the here and now.</p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;">*New vehicles- advertised price does not include applicable sales tax, title, documentation fees, license, registration, freight and set up. Buyer is responsible for shipping. Used Vehicles- advertised price does not include applicable sales tax, title, documentation fees, freight, license and registration. Buyer is responsible for shipping. Price includes all offers, and are subject to change without notice. Not all options are listed on pre-owned vehicles. Contact dealer for further details.</p><p></p>
Monster Powersports
Wauconda, IL
2023 Harley-Davidson HERITAGE SOFTAIL CLASSIC in Marengo, IL
$18,500

Used 2023 Harley-Davidson Cruiser

HERITAGE SOFTAIL CLASSIC
<p>2023 Heritage Softail bought new in June of 23. Bike is paid for and I have title in hand. I am only selling due to unforeseen circumstances. Paid just over 24000. My loss is your gain. Bike has factory Harley Leather Saddlebags as well as engine guard. Quick release luggage rack. It has not been ridden except for test rides. Bike was delivered to me new with 7 miles on the clock. It now has 8. It has been covered and garage kept since it was delivered. I don't need to sell but would like to sell before season ends. I will entertain all REASONABLE OFFERS. Serious inquiries only please. Bike is located in Marengo Illinois. Purchased at Woodstock Illinois Harley Davidson.</p>
Private Seller
Marengo, IL
2014 Harley-Davidson HERITAGE SOFTAIL in Somonauk, IL
$14,500

Used 2014 Harley-Davidson Cruiser

HERITAGE SOFTAIL
Harley Davidson Heritage Softail, metallic blue and black, 2014, low mileage, garage kept, never dropped or laid down, 103 CI, 6 speed tranny, completely stock except for crash bar, passenger seat, installed thicker and passenger foot pegs, installed footboards, still have original parts. It's a beautiful bike, the mileage is increasing a little bit due to a ride once in a while. Original owner, have clear title. Cash or cashiers check, no test ride without license and collateral.<br>Lowered price $500, would like to see it going.
Private Seller
Somonauk, IL
2019 Harley-Davidson Heritage Classic 107 CLASSIC in Shorewood, IL
$16,680

Used 2019 Harley-Davidson Cruiser

Heritage Classic 107 CLASSIC
Stock # 034214
<p>FROM THE SHADY SIDE OF THE FAMILY TREE</p><p style="margin-bottom: 1em;"></p> <strong>Used 2019 Harley-Davidson Heritage Classic 107 MOTORCYCLE FOR SALE NEAR CHICAGO, IL.</strong> <p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;">This Used 2019 Harley-Davidson Heritage Classic 107 motorcycle is for sale at Conrad’s Harley-Davidson located in Joliet, IL. If this isn't the exact vehicle you're looking for don't hesitate to go back and <strong>REVISE YOUR SEARCH</strong> . We are sure to have the perfect motorcycle for you in our showroom located in Joliet, Illinois. At Conrad’s Harley-Davidson we host a large selection of new and used motorcycles in the Chicago area. Contact Conrad’s Harley-Davidson today to <strong>SCHEDULE A TEST-RIDE</strong> . Visit Conrad’s Harley-Davidson of Joliet, your family-owned IL Harley-Davidson dealership. </p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p> <strong>CONRAD’S HARLEY-DAVIDSON </strong> <p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"><strong>Map Directions: 19356 NE Frontage Rd, Joliet, IL 60404 </strong></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"><strong>Click to Call: (815) 725-2000 </strong></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p> <strong>2019 Harley-Davidson Heritage Classic 107</strong> <p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;">The dark style, modern edge and reinvigorated ride of the Heritage model take nostalgia ripping into a new place.</p><p></p>
Conrad's Harley-Davidson*
Shorewood, IL
2018 Harley-Davidson Heritage Classic in Shorewood, IL
$17,480

Used 2018 Harley-Davidson Cruiser

Heritage Classic
Stock # 030550
<p>FROM THE SHADY SIDE OF THE FAMILY TREE</p><p style="margin-bottom: 1em;"></p> <strong>Used 2018 Harley-Davidson Heritage Classic MOTORCYCLE FOR SALE NEAR CHICAGO, IL.</strong> <p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;">This Used 2018 Harley-Davidson Heritage Classic motorcycle is for sale at Conrad’s Harley-Davidson located in Joliet, IL. If this isn't the exact vehicle you're looking for don't hesitate to go back and <strong>REVISE YOUR SEARCH</strong> . We are sure to have the perfect motorcycle for you in our showroom located in Joliet, Illinois. At Conrad’s Harley-Davidson we host a large selection of new and used motorcycles in the Chicago area. Contact Conrad’s Harley-Davidson today to <strong>SCHEDULE A TEST-RIDE</strong> . Visit Conrad’s Harley-Davidson of Joliet, your family-owned IL Harley-Davidson dealership. </p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p> <strong>CONRAD’S HARLEY-DAVIDSON </strong> <p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"><strong>Map Directions: 19356 NE Frontage Rd, Joliet, IL 60404 </strong></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"><strong>Click to Call: (815) 725-2000 </strong></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p> <strong>2018 Harley-Davidson Heritage Classic</strong> <p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;">The Heritage Classic motorcycle used to be a homage to ‘50s chrome nostalgia. Take a look at the new one, and you’ll see it’s anything but that.</p><p></p>
Conrad's Harley-Davidson*
Shorewood, IL
2013 Harley-Davidson Heritage Softail® Classic CLASSIC in Shorewood, IL
$13,780

Used 2013 Harley-Davidson Cruiser

Heritage Softail® Classic CLASSIC
Stock # 011697U
<p>Heritage Softail® Classic</p><p style="margin-bottom: 1em;"></p> <strong>Used 2013 Harley-Davidson Heritage Softail Classic MOTORCYCLE FOR SALE NEAR CHICAGO, IL.</strong> <p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;">This Used 2013 Harley-Davidson Heritage Softail Classic motorcycle is for sale at Conrad’s Harley-Davidson located in Joliet, IL. If this isn't the exact vehicle you're looking for don't hesitate to go back and <strong>REVISE YOUR SEARCH</strong> . We are sure to have the perfect motorcycle for you in our showroom located in Joliet, Illinois. At Conrad’s Harley-Davidson we host a large selection of new and used motorcycles in the Chicago area. Contact Conrad’s Harley-Davidson today to <strong>SCHEDULE A TEST-RIDE</strong> . Visit Conrad’s Harley-Davidson of Joliet, your family-owned IL Harley-Davidson dealership. </p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p> <strong>CONRAD’S HARLEY-DAVIDSON </strong> <p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"><strong>Map Directions: 19356 NE Frontage Rd, Joliet, IL 60404 </strong></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"><strong>Click to Call: (815) 725-2000 </strong></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p> <strong>2013 Harley-Davidson Heritage Softail Classic</strong> <p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;">Blazing from the past with original dresser spirit and modern touring capabilities. The 2013 Harley-Davidson® Heritage Softail® Classic motorcycle FLSTC is fully equipped with modern touring capabilities and even has a removable motorcycle windshield. For 2013,
Conrad's Harley-Davidson*
Shorewood, IL
2021 Harley-Davidson® FLHCS - Heritage Classic 114 CLASSIC in Big Bend, WI
$11,499

Used 2021 Harley-Davidson® Cruiser

FLHCS - Heritage Classic 114 CLASSIC
Stock # 050452
2021 Harley-Davidson® FLHCS - Heritage Classic 114, ONLY 10,510 MILES, 114" MOTOR, FREEDOM PERFORMANCE EXHAUST, HIGH FLOW INTAKE, UPGRADED BIG HANDLEBARS, BRAIDED LINES, QUICK DETACHABLE UPPER FAIRING, CRASH BAR, HWY PEGS, HD LED HEADLIGHT AND SPOTS, UPGRADED GRIPS, ABS, CRUISE CONTROL, KEYLESS START, SECURITY, 6-SPEED TRANS, NEW REAR TIRE, AND MORE! CLEAN AND LOADED BLACKED OUT SOFTAIL CRUISER!
Road Track And Trail
Big Bend, WI
1989 Harley-Davidson FLSTC - Heritage Softail in Big Bend, WI
$5,399

Used 1989 Harley-Davidson Touring

FLSTC - Heritage Softail
Stock # 027665
1989 Harley-Davidson FLSTC - Heritage Softail, ONLY 22,675 MILES! FULL CUSTOM PAINT! CUSTOM STRETCHED GAS TANK, CHROME BOYD WHEELS, MATCHING ROTORS, CHROME PULLEY COVER, CHROME SWING ARM COVER, CHROME FORKS, UPGRADED HANDLEBARS, CHROME HANDLEBAR CONTROLS AND MASTER CYLINDER, VANCE AND HINES EXHAUST, S&S HIGH FLOW INTAKE AND CARB, CHROME FLOORBOARDS AND INSERTS, UPGRADED MIRRORS, LEVERS, GRIPS, AND FOOT CONTROLS, UPGRADED TAIL LIGHT AND REAR SIGNAL ASSEMBLY, CHROME INNER PRIMARY COVER, WINDSHIELD, BACKREST, UPGRADED OIL COOLER, CHROME CALIPER COWER, AND MORE! CLEAN AND LOADED CUSTOM EVO SOFTAIL CRUISER!
Road Track And Trail
Big Bend, WI
2016 Harley-Davidson® Heritage Softail® Classic CLASSIC in Milwaukee, WI
$12,999

Used 2016 Harley-Davidson® Cruiser

Heritage Softail® Classic CLASSIC
Stock # U1915
2016 Harley-Davidson® Heritage Softail® Classic, <p>The Heritage Softail® Classic drips with the nostalgia of days gone by, but that’s only half of the equation for the rider of today. The hidden suspension gives you the authentic look without the bone-shaking ride of an old Hardtail. You get the comfort of cruise control for those long stretches of pavement. A redesigned seat and redesigned leather saddlebags. And best of all, a new High-Output Twin Cam 103™ engine. We’re not about to re-invent this look. But we never stop re-inventing the ride.</p>
House Of Harley-Davidson Milwaukee
Milwaukee, WI
2008 Harley-Davidson HERITAGE SOFTAIL SPECIAL in Rock City, IL
$32,995

Used 2008 Harley-Davidson Custom

HERITAGE SOFTAIL SPECIAL
<p>The 2008 Harley-Davidson Heritage Softail Special is a custom motorcycle that offers a unique riding experience. This one-of-a-kind bike has an estimated $50,000 invested. With only 6878 miles on the odometer, this bike has plenty of life left to offer its next owner. This motorcycle was a build by DD Custom Cycles, one of the Top Bagger Builders in the country. The custom orange/copper paint job with chrome accents on this bike make it stand out on the road, turning heads wherever it goes. The 2008 model year is known for its reliable performance and durability, and with upgraded air shocks this Heritage Softail will provide many more miles of enjoyment. If you're in the market for a custom motorcycle that offers both style and substance, the 2008 Harley-Davidson Heritage Softail Special is a great choice. With its low mileage and well-maintained condition, this bike is ready to hit the open road and provide years of riding pleasure. Don't miss out on the opportunity to own a piece of motorcycle history with a custom flair, with this exceptional Harley-Davidson model.</p>
Private Seller
Rock City, IL
2013 Harley-Davidson Heritage Softail® Classic CLASSIC in Davenport, IA
$11,599

Used 2013 Harley-Davidson Cruiser

Heritage Softail® Classic CLASSIC
Stock # 014754
<p>Vance & Hines Slip-On Pipes, Luggage Rack, Crash Bar, Passenger Floorboards, and Backrest with Luggage Rack</p><p style="margin-bottom: 1em;">Blazing from the past with original dresser spirit and modern touring capabilities. The 2013 Harley-Davidson® Heritage Softail® Classic motorcycle FLSTC is fully equipped with modern touring capabilities and even has a removable motorcycle windshield. For 2013, the FLSTC Heritage Softail Classic comes in a limited, serialized 110th Anniversary Special Edition, featuring exclusive commemorative anniversary styling elements and premium features that make it a top-of-the-line model and a true work of living art, with finely forged finishes that age and transform in a manner unique to each vehicle. The Harley® Heritage Softail Classic model features a powerful air-cooled Twin Cam 103™ Harley engine with 6-speed Cruise Drive® transmission, providing more performance power for passing, hill-climbing, and riding with passenger and luggage. Enjoy mile after mile with a large capacity 5 gal. Softail fuel tank. The H-D® Softail model's tank is also dripping with authentic Harley-Davidson style. The Harley FLSTC model has full length rider footboards with rubber vibration isolation for added comfort. Another of the many great features of this classic motorcycle is the detachable motorcycle windshield. You can remove the Harley Heritage Softail windshield for a new look. Learn more about the style and functional components found on this bike. If you're looking for a pure classic cruiser motorcycle, check out the Fat Boy® model. The Harley touring motorcycles are also well worth a look including the Electra Glide® Ultra Limited touring bike.</p><p></p>
Hawkeye Motorworks
Davenport, IA
2022 Harley-Davidson HERITAGE SOFTAIL CLASSIC CLASSIC in Barrington, IL
$17,595

Used 2022 Harley-Davidson Cruiser

HERITAGE SOFTAIL CLASSIC CLASSIC
Stock # P623A
<p>This used one owner Harley Davidson Heritage Softail Classic is for sale at Cycle Werks in Barrington in Barrington IL and is in excellent condition with only 3126 miles.  Our service department has inspected the bike and performed a fresh oil and oil filter change so this bike is ready to ride.  In addition to the impressive list of standard features on the bike the previous owner also installed Engine Guards, Saddle Bag Guards, Passenger Backrest, Cargo Rack and a Battery Tender Lead.</p><p><br> </p>
Cycle Werks in Barrington
Barrington, IL
2006 Harley-Davidson Heritage Softail® in Roselle, IL
$6,499

Used 2006 Harley-Davidson Cruiser

Heritage Softail®
Stock # 032025A
<p>Heritage Softail®</p>In the saddle of a Harley-Davidson® Softail®, no road is ever lonely. Sunlight breaks through treetops to dance on chromed steel. The wind offers its constant stream of praise. And the world unfolds before you with open arms. Maybe it’s because nothing else on the road compares with the timeless hardtail styling ... and nothing else feels like a Twin Cam 88B™ power mill rigid-mounted to the frame. Counterbalancing takes care of all but the good vibrations. You and the motorcycle become one, united by an unbreakable bond. Then you feel the hidden rear suspension smooth out the ride with a full 4" of travel. There’s no denying you’re in the saddle of a rolling masterpiece. This year, the Softail family of custom motorcycles welcomes its latest member. We invite you to turn the page and take a gander at the clean lines of the new Heritage Softail®. Additionally, all new bobtail models get a shot of adrenaline in the hindquarters — a brawny, road-hugging 200mm tire under a new wider fender. More rubber to stick to the pavement. More style to keep the eyes glued.Everyone loves a clean-looking bike. The Heritage Softail® is a fine example. A motorcycle gleaming with simplicity. With a machine this pure, it’s only fitting we start with the heart and soul. Get a good look at the silver powder-coated Twin Cam 88B™ engine. It’s rigid-mounted and counterbalanced. Next feast your eyes on the hardtail styling. Any paint color you choose will look great with the machete tank graphics. A horseshoe oil tank and Laced wheels complete the no-nonsense look. The price is stripped-down, too — it’s the most affordable FL model. There’s even a detachable passenger pillion. Sometimes the less you see on a bike, the more there is to admire.<p></p>
Top Gear Powersports, Inc
Roselle, IL
2007 Harley-Davidson Heritage Softail CLASSIC in Hawthorn Woods, IL
$7,250

Used 2007 Harley-Davidson Cruiser

Heritage Softail CLASSIC
Harley-Davidson Heritage Softail in amazing shape!-Low Miles! 17,500 miles-Clean title in hand-Vance and Hines Exhaust-All lights work-Starts right up-Has trickle charge and jump harness installed-All original studded seat and bags in great shape-Has rear seat with sissy bar and 6 pack rack-Also come with a brand new set of locking Viking saddle bags ($400)Maintained with Syn3 in engine, trans, and primary.
Private Seller
Hawthorn Woods, IL
2021 Harley-Davidson Heritage Classic 114 CLASSIC in Wauconda, IL
$14,999

Used 2021 Harley-Davidson Cruiser

Heritage Classic 114 CLASSIC
Stock # WF3338
<p>Light Bar Kit!</p><p style="margin-bottom: 1em;">The quintessential American cruiser. Showstopping vintage details and pure rock and roll style.</p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;">*New vehicles- advertised price does not include applicable sales tax, title, documentation fees, license, registration, freight and set up. Buyer is responsible for shipping. Used Vehicles- advertised price does not include applicable sales tax, title, documentation fees, freight, license and registration. Buyer is responsible for shipping. Price includes all offers, and are subject to change without notice. Not all options are listed on pre-owned vehicles. Contact dealer for further details.</p><p></p>
Monster Powersports
Wauconda, IL
2020 Harley-Davidson Heritage Classic 114 CLASSIC in Wauconda, IL
$14,999

Used 2020 Harley-Davidson Cruiser

Heritage Classic 114 CLASSIC
Stock # WF5113
<p>Windshield, Light Bar Kit, Highway Bars and Vance & Hines Pipes!</p><p style="margin-bottom: 1em;">The refined finishes, modern edge and reinvigorated ride of the Heritage model take nostalgia ripping into the here and now.</p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;">*New vehicles- advertised price does not include applicable sales tax, title, documentation fees, license, registration, freight and set up. Buyer is responsible for shipping. Used Vehicles- advertised price does not include applicable sales tax, title, documentation fees, freight, license and registration. Buyer is responsible for shipping. Price includes all offers, and are subject to change without notice. Not all options are listed on pre-owned vehicles. Contact dealer for further details.</p><p></p>
Monster Powersports
Wauconda, IL
2019 Harley-Davidson Heritage Classic 114 CLASSIC in Wauconda, IL
$13,999

Used 2019 Harley-Davidson Cruiser

Heritage Classic 114 CLASSIC
Stock # 039661
<p>Windshield, Light Bar Kit, Quick Release Tour Pack and Luggage Rack!</p><p style="margin-bottom: 1em;">The dark style, modern edge and reinvigorated ride of the Heritage model take nostalgia ripping into a new place.</p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;">*New vehicles- advertised price does not include applicable sales tax, title, documentation fees, license, registration, freight and set up. Buyer is responsible for shipping. Used Vehicles- advertised price does not include applicable sales tax, title, documentation fees, freight, license and registration. Buyer is responsible for shipping. Price includes all offers, and are subject to change without notice. Not all options are listed on pre-owned vehicles. Contact dealer for further details.</p><p></p>
Monster Powersports
Wauconda, IL
2017 Harley-Davidson Heritage Softail® Classic CLASSIC in Wauconda, IL
$10,499

Used 2017 Harley-Davidson Cruiser

Heritage Softail® Classic CLASSIC
Stock # AC28379
<p>Windshield, Light Bar Kit, Highway Bars, Vance & Hines Pipes, Passenger Backrest and Luggage Rack!</p><p style="margin-bottom: 1em;">This is too good to consign to history.</p><p style="margin-bottom: 1em;">The Heritage Softail® Classic drips with the nostalgia of days gone by, but that’s only half of the equation for the rider of today. The hidden suspension gives you the authentic look without the bone-shaking ride of an old Hardtail. You get the comfort of cruise control for those long stretches of pavement. A redesigned seat and redesigned leather saddlebags. And best of all, the High Output Twin Cam 103B™ engine. We’re not about to re-invent this look. But we never stop re-inventing the ride.</p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;">*New vehicles- advertised price does not include applicable sales tax, title, documentation fees, license, registration, freight and set up. Buyer is responsible for shipping. Used Vehicles- advertised price does not include applicable sales tax, title, documentation fees, freight, license and registration. Buyer is responsible for shipping. Price includes all offers, and are subject to change without notice. Not all options are listed on pre-owned vehicles. Contact dealer for further details.</p><p></p>
Monster Powersports
Wauconda, IL
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