Value
BUY
Sell

Search

Red Harley-Davidson HERITAGE SOFTAIL Motorcycles for Sale in smyrna, Delaware

Looking to buy a Harley-Davidson Heritage Softail motorcycle in Smyrna, Delaware? Browse our extensive inventory of new and used Harley-Davidson Heritage Softail motorcycles from local Harley-Davidson dealers and private sellers in Smyrna, Delaware. Compare prices, models, trims, options and specifications between different Harley-Davidson motorcycles on Cycle Trader.
close
38

66 Harley-Davidson HERITAGE SOFTAIL Motorcycles For Sale

2009 Harley-Davidson® Heritage Softail® Classic CLASSIC in Chadds Ford, PA
$10,991

Used 2009 Harley-Davidson® Cruiser

Heritage Softail® Classic CLASSIC
Stock # 028640UHH
2009 Harley-Davidson® Heritage Softail® Classic, <p>Rolling on new signature wide whitewall tyres, the Heritage Softail Classic receives a number of other more-subtle styling changes and new components that shift this popular model in a new, even more retro direction for 2009. The beefy FL front end features a front fender and chrome headlight nacelle with clean new styling cues, while taller handlebars change the rider’s profile. The fuel tank has new glass-filled, 3-D badges and is topped with a classic “cat’s eye” console. Half-moon rider footboards and a large, oval foot brake pad also nod to the past. The passenger seat and backrest have been revised for more comfort, while the rider seat has new trim that matches a leather console panel, revised saddle bag trim, and new sissy bar trim. The passenger seat and backrest and the king-size windshield can be quickly detached for more streamlined cruising. </p>
Brandywine Harley-Davidson
Chadds Ford, PA
2022 Harley-Davidson® FLHCS - Heritage Classic 114 CLASSIC in Darlington, MD
$13,888

Used 2022 Harley-Davidson® Cruiser

FLHCS - Heritage Classic 114 CLASSIC
Stock # 065397
2022 Harley-Davidson® FLHCS - Heritage Classic 114, ONE OWNER, GREAT COLOR COMBINATION, BLACK FINISH, READY TO RIDE!<br /> <br /> 2022 Harley-Davidson® Heritage Classic 114 <p>The quintessential American cruiser. Showstopping vintage details and pure rock and roll style.</p><p><strong>Features may include:</strong></p><strong>THIS IS THE RIGHT BIKE FOR</strong><ul><li>Riders ready to chase excitement across state lines</li></ul><ul><li>Highway riding with full fenders and detachable windscreen</li></ul><ul><li>Milwaukee-Eight® 114 V-Twin engine and steel laced wheels</li></ul><ul><li>MILWAUKEE-EIGHT® BIG TWIN ENGINE</li></ul><p>A powerful, cool-running engine with crisp throttle response and a pure, soul-satisfying rumble.</p><ul><li>LOCKABLE AND SEALED SADDLEBAGS</li></ul><p>A sleek look on the outside and roomy on the inside with enough space to stash your riding essentials. The lids open with one touch.</p><ul><li>DETACHABLE WINDSCREEN</li></ul><p>Go from touring to cruising in a heartbeat. Leave the screen on for a clean envelope of air over the long haul. Or remove it in seconds for a completely new look and ride.</p><ul><li>HIGH PERFORMANCE REAR MONO SHOCK</li></ul><p>Easily adjustable mono-shock rear suspension allows for dynamic cornering capability while preserving the hardtail look.</p>
Eisenhauer's Chesapeake Harley-Davidson
Darlington, MD
2021 Harley-Davidson® FLHCS - Heritage Classic 114 CLASSIC in Darlington, MD
$14,888

Used 2021 Harley-Davidson® Touring

FLHCS - Heritage Classic 114 CLASSIC
Stock # 068066
2021 Harley-Davidson® FLHCS - Heritage Classic 114, ONE OWNER, FRESH SERVICE, READY TO RIDE!<br /> <br /> 2021 Harley-Davidson® Heritage Classic 114 <p>The quintessential American cruiser. Showstopping vintage details and pure rock and roll style.</p><strong>Features May Include</strong><p><strong>THIS IS THE RIGHT BIKE FOR</strong></p><ul><li>Riders ready to chase excitement across state lines</li></ul><ul><li>Highway riding with full fenders and detachable windscreen</li></ul><ul><li>Milwaukee-Eight® 107 or 114 V-Twin engine and steel laced wheels</li></ul><ul><li>MILWAUKEE-EIGHT® BIG TWIN ENGINE</li></ul><p>A powerful, cool-running engine with crisp throttle response and a pure, soul-satisfying rumble.</p><ul><li>SOFTAIL® FRAME</li></ul><p>The frame retains the classic Softail® lines, but its lightweight design and stiffness translate to a responsive ride unlike anything you’ve felt before.</p><ul><li>A DARK CLASSIC WITH MODERN EDGE</li></ul><p>Dripping with gangster-era style and vintage details. If Bonnie and Clyde rode a Harley® motorcycle, this would be the one.</p><ul><li>SIGNATURE LED FORWARD LIGHTING</li></ul><p>Darkness-defying lighting that gives you great visibility at night.</p><ul><li>LOCKABLE AND SEALED SADDLEBAGS</li></ul><p>A sleek look on the outside and roomy on the inside with enough space to stash your riding essentials. The lids open with one touch.</p><ul><li>DETACHABLE WINDSCREEN</li></ul><p>Go from touring to cruising in a heartbeat. Leave the screen on for a clean envelope of air over the long haul. Or remove it in seconds for a completely new look and ride. </p><ul><li>HIGH PERFORMANCE REAR MONO SHOCK</li></ul><p>Easily adjustable mono-shock rear suspension allows for dynamic cornering capability while preserving the hardtail look.</p>
Eisenhauer's Chesapeake Harley-Davidson
Darlington, MD
2020 Harley-Davidson Heritage Classic 114 CLASSIC in Blades, DE
$15,999

Used 2020 Harley-Davidson Cruiser

Heritage Classic 114 CLASSIC
Stock # HAR032543
<p>Experience Timeless Style and Power with the 2020 Harley-Davidson Heritage Classic 114 at Indian Motorcycle of Seaford</p><p style="margin-bottom: 1em;"> As the season changes, discover the allure of classic American motorcycling with the 2020 Harley-Davidson Heritage Classic 114 – a motorcycle that embodies heritage, power, and the joy of the open road.</p><p style="margin-bottom: 1em;">The 2020 Harley-Davidson Heritage Classic 114 is a true classic cruiser. Its design, featuring timeless lines and iconic styling, pays tribute to Harley-Davidson's rich heritage. Powered by the robust Milwaukee-Eight 114 engine, it delivers commanding power and torque, ensuring a ride that's as thrilling as it is iconic. With modern technology, comfortable ergonomics, and the unmistakable Harley-Davidson rumble, it's a motorcycle that defines the spirit of American touring.</p><p style="margin-bottom: 1em;">Visit Indian Motorcycle of Seaford, where we celebrate the legacy of American motorcycles. We're more than a dealership; we're a community of riders who appreciate the beauty of classic bikes. This fall, let the Harley-Davidson Heritage Classic 114 be your trusted companion as you explore winding roads, create lasting memories, and savor the beauty of the season.</p><p style="margin-bottom: 1em;">Ride with classic elegance. Embrace the heritage with the 2020 Harley-Davidson Heritage Classic 114.</p><p></p>
Indian Motorcycle of Seaford
Blades, DE
2018 Harley-Davidson Heritage Classic 114 CLASSIC in Willow Valley Pike, PA
$14,491

Used 2018 Harley-Davidson Cruiser

Heritage Classic 114 CLASSIC
Stock # 011052
2018 Harley-Davidson Heritage Classic 114, The Heritage Softail Classic used to be an homage to 50s chrome nostalgia. Take a look at the new one, and you ll see it s anything but that. The history is still there, and now it s done with a dark style and a modern edge and a totally reinvigorated ride. At the heart of it all, you get a blacked-out Milwaukee-Eight V-Twin engine. You also get the reduced weight, awesome acceleration, and smooth ride of an all-new Softail motorcycle. It features a windshield and hard saddlebags for light touring. It all comes together for a great ride and a look that s going to make an impression in any town you roll into. Available in 107 and 114 engine displacements.Heritage Softail Classic with touring accessories. Harley-Davidson Genuine Motor Accessories give you unlimited options for customizing the function and look of your bike. Like this one that s outfitted for long highway miles.
Lancaster Harley-Davidson
Willow Valley Pike, PA
2007 Harley-Davidson HERITAGE SOFTAIL CLASSIC in Cockeysville, MD
$5,000

Used 2007 Harley-Davidson Cruiser

HERITAGE SOFTAIL CLASSIC
2007 Heritage Softail® Classic with 38850 miles. Several Willie G chrome parts / covers added. Last major service included new tires & new brakes. (Less than 1000 miles). New battery installed August 2023. Detachable windshield. Highway pegs. Comfortable passenger pillion, backrest and floorboards. Saddlebags included. ThunderStar wheels (showing some wear). Runs and sounds great with plenty of power. Please review photos as they serve as part of the description. No tire kickers or joy riders. Serious buyers only. Nelson-Rigg cover included. Original owner's manual & a service manual on CD included. Clean / clear title.
Private Seller
Cockeysville, MD
2014 Harley-Davidson Heritage Softail Classic CLASSIC in Boyertown, PA
$11,995

Used 2014 Harley-Davidson Cruiser

Heritage Softail Classic CLASSIC
Stock # J25351
2014 Harley-Davidson Heritage Softail Classic, <p><strong>NEW MARTIN MOTO ARRIVAL</strong></p> <p><strong>Our factory trained technicians inspect and test ride every vehicle brought into our inventory . Once a unit has undergone our 50 point inspection it then gets offered up to the general public for sale. If you are interested in purchasing one of our "Coming Soon" units, we can take a refundable deposit which prioritizes it through the Martin Moto inspection process. After this we will post multiple photos, the work performed, and the cosmetic condition on the website for you to see. If you have a change of heart, we will refund your deposit or swap it to another vehicle, whichever you prefer. For more details or questions please contact one of our team members at 610-369-3120.</strong></p>
MARTIN MOTO
Boyertown, PA
2012 Harley-Davidson Heritage Softail Classic CLASSIC in Manheim, PA
$9,295

Used 2012 Harley-Davidson Cruiser

Heritage Softail Classic CLASSIC
Stock # 019437C
2012 Harley-Davidson Heritage Softail Classic, Nice clean Heritage Softail with low miles!With its smooth performance, comfortable riding position, low seat height, ample luggage space, wind protection and passenger accommodations, the Heritage Softail Classic is a true custom-touring bike. The quick-release Lexan windshield allows for quick conversion to custom cruising. Few bikes capture the spirit of the original dressers more authentically than this beautiful motorcycle. 1940s-style leather saddlebags with quick-detach buckles, full FL front fender, chrome laced wheels and hub cover all pay homage to the past, while the counter-balanced Twin Cam 96 engine, hidden rear suspension and new optional Anti-lock Braking System all reside at the forefront of modern technology.
Iron Valley Harley-Davidson
Manheim, PA
1999 Harley-Davidson Heritage Softail Classic CLASSIC in Manheim, PA
$5,995

Used 1999 Harley-Davidson Cruiser

Heritage Softail Classic CLASSIC
Stock # 059119
1999 Harley-Davidson® Heritage Softail Classic, <strong> Old School Heritage ready for a new home! </strong> <p>The 1999 Harley-Davidson Heritage Softail Classic model is a Custom / cruiser bike manufactured by Harley-Davidson. The dry weight is 698.4 pounds and it is equipped with a V2, four-stroke motor. The engine produces a maximum peak output power of 56.00 HP @ 5000 RPM. With this drive-train, the Harley-Davidson Heritage Softail Classic is capable of reaching a maximum top speed of 93.2 mph.</p>
Iron Valley Harley-Davidson
Manheim, PA
2009 Harley-Davidson Heritage Softail CLASSIC in Etters, PA
$7,650

Used 2009 Harley-Davidson Cruiser

Heritage Softail CLASSIC
In great shape! Lots of upgrades and add-ons:  Mini-apes (also have original bars); wind deflectors; highway pegs; engine guards; new front LED headlamp & passing lamps; upgraded odometer/speedometer/tachometer; chrome front wheel bolt covers; “Live to Ride…” emblem gas cap and air cleaner cover; tank bib with pocket; windshield bag; upgraded oil temp gauge, new Mustang touring seat with removable driver backrest, and new Mustang touring pillion installed less than 150 miles ago (also have original seats); Saddleman detachable tail bag; battery charger/tender.  New battery about 1,500 miles ago. This bike was well-maintained annually with proper oil, lube, fluids, etc. service done.  Always garage-kept with battery tender on.  New tires with less than 2,000 miles on them. Price is well below KBB price point.
Private Seller
Etters, PA
2022 Harley-Davidson HERITAGE CLASSIC in West Long Branch, NJ
$21,499

Used 2022 Harley-Davidson Cruiser

HERITAGE CLASSIC
Stock # R616427A
<p>LIKE NEW, CLASSIC COLORED HERITAGE, SAVING YOU THOUSANDS! PLEASE CALL AND ASK FOR DAN TODAY (732)229-8518</p><p style="margin-bottom: 1em;">THIS 2022 H-D HERITAGE CLASSIC, OFFERED WITH JUST 248 MILES, IN BILLIARD RED / VIVID BLACK W/ PINSTRIPE AND BLACK FINISH IS A TRUE CLASSIC! COME TAKE ADVANTAGE OF SOME NICE UPGRADES LIKE COBRA USA SLIP-ON EXHAUST AND UPGRADED WILLIE G TRIM PIECES. THIS IS THE ONE TO CONSIDER AND MAKE YOURS THIS SUMMER! PLEASE CALL DAN FOR MORE INFORMATION AND APPOINTMENT (732)229-8518. </p><p></p>
Shoreline Harley-Davidson
West Long Branch, NJ
2001 Harley-Davidson HERITAGE SOFTAIL CLASSIC CLASSIC in Fayetteville, PA
$6,995

Used 2001 Harley-Davidson Cruiser

HERITAGE SOFTAIL CLASSIC CLASSIC
Stock # 2257
2001 Harley-Davidson HERITAGE SOFTAIL CLASSIC, 2001 HERITAGE SOFTAIL CLASSIC, ** CAM CHAIN TENSOINERS HAVE BEEN REPLACED**WELL MAINTAINED WITH RECENT SERVICE RECORDS AVAILABLE. , CHROME FORKS, DETACHABLE SISSYBAR ,THICK RUBBER ON TIRES, FRESH OIL CHANGE, NEW PA INSPECTION, VERY NICE PAINT AND CHROME, RUNS STRONG AND RIDES SMOOTH !! ** NO DEALER FEES EVER** Star Auto Sales 4572 Lincoln way east Fayetteville, pa. 17222 717-352-8182 www.starautopa.net
Star Auto Sales
Fayetteville, PA
2015 Harley-Davidson Heritage Softail® Classic CLASSIC in Fredericksburg, VA
$9,495

Used 2015 Harley-Davidson Cruiser

Heritage Softail® Classic CLASSIC
Stock # 11219
<p>Heritage Softail® Classic</p><p style="margin-bottom: 1em;"><strong>Certified Pre-Owned Motorcycle Includes a 30 Day / 1500 Mile Warranty. Extended Warranty Plans Available. </strong></p><p style="margin-bottom: 1em;">This 2015 Harley-Davidson Heritage Softail Classic features a fuel injected 103" Twin Cam motor and 6 speed transmission. This Certified motorcycle received a full service at our dealership. </p><p style="margin-bottom: 1em;"><strong>Accessories Include:</strong></p><ul><li>ABS Brakes</li><li>Slash Cut Mufflers</li><li>Screamin' Eagle Intake</li><li>Engine Guard</li><li>Windshield Pouches</li></ul><p style="margin-bottom: 1em;"><strong>***Financing Available!***</strong></p><p style="margin-bottom: 1em;">Classic Iron has been in the motorcycle industry for 30 years and features Virginia's largest Pre-Owned Inventory. We have over 300 units in stock! We have financing available and are open Monday-Friday 9-6 & Saturdays 9-4. If you have any questions please call 540-479-1114 or email sales@classiciron.com</p><p style="margin-bottom: 1em;"> The bike you look at today, and want to think about tonight, before buying it tomorrow, will be bought today, by someone who looked at it yesterday, and thought about it last night! </p><p></p>
Classic Iron Inc
Fredericksburg, VA
2009 Harley-Davidson Heritage Softail® Classic CLASSIC in Fredericksburg, VA
$7,995

Used 2009 Harley-Davidson Cruiser

Heritage Softail® Classic CLASSIC
Stock # 11021
<p>Heritage Softail® Classic</p><p style="margin-bottom: 1em;"><strong>Certified Pre-Owned Motorcycle Includes a 30 Day / 1500 Mile Warranty. Extended Warranty Plans Available. </strong></p><p style="margin-bottom: 1em;">This 2009 Harley-Davidson Heritage Softail Classic features a fuel injected 96" Twin Cam motor and 6 speed transmission. This Certified motorcycle received 2 new tires as well as a full service at our dealership. </p><p style="margin-bottom: 1em;"><strong>Accessories Include:</strong></p><ul><li>2 into 1 Vance & Hines Exhaust</li><li>Upgraded Air Filter</li><li>Windshield Pouch</li></ul><p style="margin-bottom: 1em;"><strong>***Financing Available!***</strong></p><p style="margin-bottom: 1em;">Classic Iron has been in the motorcycle industry for 30 years and features Virginia's largest Pre-Owned Inventory. We have over 300 units in stock! We have financing available and are open Monday-Friday 9-6 & Saturdays 9-4. If you have any questions please call 540-479-1114 or email sales@classiciron.com</p><p style="margin-bottom: 1em;"> The bike you look at today, and want to think about tonight, before buying it tomorrow, will be bought today, by someone who looked at it yesterday, and thought about it last night! </p><p></p>
Classic Iron Inc
Fredericksburg, VA
2005 Harley-Davidson HERITAGE SOFTAIL in Fredericksburg, VA
$6,000

Used 2005 Harley-Davidson Cruiser

HERITAGE SOFTAIL
Reduced for quick sale. In EXCELLENT condition. Many extras included (brand new windshield, leather hard bags, leather cargo box, passenger seat with back rest and cargo rack, extra passenger seat, and comes with an extra main seat.The 2005 Harley-Davidson Heritage Softail is a classic cruiser motorcycle that exudes timeless style and superior performance. This iconic bike is a popular choice among riders who value the combination of heritage and modern technology. With only 19,300 miles on the odometer, this Harley is in excellent condition and is ready to hit the open road.The Heritage Softail is powered by a powerful V-twin engine that delivers smooth and responsive acceleration. Its comfortable seating position and plush suspension make long rides a breeze, while the classic styling turns heads wherever you go. The distinctive Harley-Davidson logo and chrome accents add to the bike's appeal, giving it a truly unique look.This motorcycle is perfect for cruising around town or taking on longer journeys on the highway. The Heritage Softails low center of gravity and balanced weight distribution make it easy to handle in a variety of riding conditions. Whether you're a seasoned rider or new to the world of motorcycles, this Harley is sure to provide an unforgettable riding experience.When it comes to reliability and durability, Harley-Davidson motorcycles are known for their quality construction and attention to detail. This 2005 Heritage Softail is no exception, with its solid build and dependable performance. With proper maintenance and care, this bike will provide years of enjoyment for its lucky owner.Overall, the 2005 Harley-Davidson Heritage Softail is a top choice for riders who appreciate the combination of classic style and modern performance. With its low mileage and well-maintained condition, this bike is a great investment for anyone looking to own a piece of motorcycle history. Don't miss your chance to own this iconic Harley-Davidson motorcycle and experience the thrill of the open road like never before.
Private Seller
Fredericksburg, VA
2021 Harley-Davidson Heritage Classic 107 CLASSIC in Long Island City, NY
$13,588

Used 2021 Harley-Davidson Cruiser

Heritage Classic 107 CLASSIC
Stock # U044405-1
2021 Harley-Davidson Heritage Classic 107, 2021 Crimson/White Heritage Classic with only 4,498 miles. The Softail Heritage Classic brings you the nostalgic feel with the traditional styling. The hard leather saddlebags provide plenty of storage for all your gear while you cruise the streets. The chrome design with the laced wheels is part of what so many love with the old school style. Come by today to feel the comfort of the Softail!
New York City Harley-Davidson
Long Island City, NY
Purchase In Progress
Another customer has started purchasing this motorcycle. By providing your information below, we can let you know if this motorcycle becomes available again.
Please enter a valid first name.
Please enter a valid last name.
Please enter a valid email.
Please enter a valid phone number.
By using this site, you agree to our Terms of Use & our Privacy Policy.
Disclaimers

Cycle Trader Disclaimer: The information provided for each listing is supplied by the seller and/or other third parties. CycleTrader.com is not responsible for the accuracy of the information. Please refer to the Cycle Trader Terms of Use for further information.


Download Our App