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Gray Harley-Davidson Cruiser Motorcycles for Sale in winchester, Virginia

Looking to buy a Harley-Davidson cruiser in Winchester, Virginia? Browse our extensive inventory of new and used Harley-Davidson cruiser from local Harley-Davidson dealers and private sellers in Winchester, Virginia. Compare prices, models, trims, options and specifications between different Harley-Davidson cruisers on Cycle Trader.
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137 Harley-Davidson Motorcycles For Sale

2021 Harley-Davidson FAT BOY 114 in Rockvile, MD
$15,000

Used 2021 Harley-Davidson Cruiser

FAT BOY 114
<p>Used 2021 HARLEY-DAVIDSON FAT BOY 114 for sale</p><p>The 2021 Harley Davidson Fat Boy embodies classic American muscle with its iconic design and powerful performance. Boasting a massive Milwaukee-Eight engine, it roars with authority on the road while maintaining a timeless aesthetic with its fat tires, solid disc wheels, and signature chrome finishes. With modern technology seamlessly integrated, this beast offers a thrilling ride that pays homage to its legendary heritage.</p><p>One Owner, very low milage.</p><p>Asking $15,000 OBO</p><p>I'm still doing payments on this bike, so will need to pay off.</p><p>Clean title</p><p>Test drive are welcome with money on hands.</p>
Private Seller
Rockvile, MD
2022 Harley-Davidson LOW RIDER S S in Port Deposit, MD
$13,999

Used 2022 Harley-Davidson Cruiser

LOW RIDER S S
<p>Great condition 2022 Low Rider S with 1,000 miles. This bike has been serviced by a HD dealership at the 1,100 miles with fully synthetic oil,. Comes with everything in the pictures. I ran the VIN against a NMVTIS authorized website: https://vincheck.info/check/nmvtis-report.php?id=910709573586</p><p><br></p><p>Vance and Hines slip-ons</p><p>External speaker with Bluetooth</p><p>Quick connect passenger seat</p><p>Quick connect windshield</p><p>Stock headlight cover</p><p>Upgraded HD two-up seat</p><p>Engine guards</p><p>Upgraded denali soundbomb horn</p>
Private Seller
Port Deposit, MD
2009 Harley-Davidson® FXSTC - Softail® Custom CUSTOM in Hagerstown, MD
$6,799

Used 2009 Harley-Davidson® Cruiser

FXSTC - Softail® Custom CUSTOM
Stock # UH5501
2009 Harley-Davidson® FXSTC - Softail® Custom, 2009 Harley-Davidson® Softail® Custom <p>The FXSTC Softail® Custom puts fists in the breeze and feet forward with a chopper profile straight from the FX custom era. The tufted king/queen seat has chrome buttons and flows up an integrated aluminum one-piece backrest, providing a comfortable perch for rider and passenger. A new low-profile front fender hugs the 21-inch laced front wheel and tire. Profile ape-hanger handlebar on custom risers and the Fat Bob® fuel tank with embossed leather tank strap and triple laid custom graphics accentuate the cool look. A 200 mm rear tire and Bobtail fender add authority to the rear end, while chrome details on the powertrain and oil tank contrast the black powder-coated engine.</p>
Twigg Cycles, Inc
Hagerstown, MD
2020 Harley-Davidson CVO STREET GLIDE CVO in Frederick, MD
$29,999

Used 2020 Harley-Davidson Cruiser

CVO STREET GLIDE CVO
Stock # 956156
2020 HARLEY-DAVIDSON CVO STREET GLIDE, <br/> <p>The pinnacle of the custom touring look taken to the edge and loaded with power. No corners were cut, no shortcuts were taken. We sweat every detail and then polished it like a jewel.</p> <ul class=primaryProductFeatures>;</ul> Key Features <ul class=itemGroupFeatures><li id=97026726 class=productFeature>Milwaukee-Eight 117 Twin-Cooled Engine: The most powerful Twin-Cooled V-Twin engine ever offered from the H-D factory, and only available in CVO models. Features color accented Rocker Box Lowers with Blaze Red finish.</li><li id=97026727 class=productFeature>H-D Connect Service: With subscription-based cellular connectivity, you can connect to your bike through your smart phone using the latest version of the Harley-Davidson App. Check your bike's vitals including fuel level, get tamper alerts and stolen-vehicle tracking, and more.</li><li id=97026728 class=productFeature>Reflex Defensive Rider Systems: A new collection of technologies that help give you confidence and control in less-than-ideal situations. The systems utilize advanced chassis control, electronic brake control and powertrain technology to assist you with accelerating and braking in a straight line or while in a turn.</li><li id=97026729 class=productFeature>Premium Paint and Finishes: Exclusive paint colors and designs executed to a level of intricate quality that is unmatched in the motorcycle and automotive categories.</li><li id=97026730 class=productFeature>High-Performance Front and Rear Suspension: Dual bending valve front suspension and emulsion rear suspension with hand-adjustable pre-load put you in control of a plush ride.</li><li id=97026731 class=productFeature>BOOM! GTS Infotainment System: An evolved interface experience that offers a contemporary look, feel and function, with exceptional durability and features designed specifically for motorcycling. Every element is optimized to enhance the rider's interaction with the bike and connectivity with the world.</li><li id=97026732 class=productFeature>Daymaker Adaptive LED Headlamp: The most-advanced headlamp system ever developed for a Harley-Davidson motorcycle. Features a signature LED light outer ring that operates as a position lamp, and additional LED lights that activate based on the lean of the bike to project light into corners to illuminate areas of the road that are unlit by traditional LED headlamps.</li><li id=97026733 class=productFeature>Fugitive Cast Aluminium Wheels: The premium hot rod bagger look is complete with Front 19-inch and Rear 18-inch wheels finished in Gloss Black/Satin.</li>
JT Motorsports
Frederick, MD
2019 Harley-Davidson Softail Slim SLIM in Manassas, VA
$12,999

Used 2019 Harley-Davidson Cruiser

Softail Slim SLIM
Stock # DT0535A
2019 Harley-Davidson Softail Slim, The stripped-down, souped-up, post WWII era look of the bobber is running stronger than ever in the Softail Slim model. You get the classic look of spoked wheels, chopped mudguards and footboards. And a ride straight out of right now. It s 16 kilograms lighter, with greater lean angle, than Slim models from just a couple of years ago. And you get the power and soul-satisfying sound of the Milwaukee-Eight 107 V-Twin engine to take you into the future. Fast.
Bull Run Harley-Davidson
Manassas, VA
2020 Harley-Davidson Breakout® 114 in Gaithersburg, MD
$15,795

Used 2020 Harley-Davidson Cruiser

Breakout® 114
Stock # HAR029378
<p>LONG, LEAN MUSCLE TAKEN TO THE MODERN EDGE</p><p style="margin-bottom: 1em;">Cyclemax has this Pre-Owned 2020 Harley-Davidson Breakout 114 available. Ask about upgrades!</p><p style="margin-bottom: 1em;">* Our Advertised Price is our best price and is offered to everyone, no need to haggle.</p><p style="margin-bottom: 1em;">* Price Includes all Dealer Fees and Charges. NO OTHER HIDDEN CHARGES !</p><p style="margin-bottom: 1em;">* Only your State Sales Tax, Insp, Title And Registration Fees are Additional.</p><p style="margin-bottom: 1em;">TRADES WELCOME! We buy bikes also! We will make a fair offer for your bike whether you buy a bike from us or not.</p><p style="margin-bottom: 1em;">CYCLEMAX SPECIALIZES IN QUALITY PRE-OWNED MOTORCYCLES.</p><p style="margin-bottom: 1em;">Cyclemax pre-owned motorcycles are always fully inspected by our certified technicians, we perform any needed service and maintenance and guarantee the bike to be in perfect working order.</p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;"></p><p style="margin-bottom: 1em;">The Breakout is a muscular modern chopper with pure ‘stop you in your tracks’ attitude. Be seen. Be respected. And when the light turns green, be gone.</p><p style="margin-bottom: 1em;">The 2020 Harley-Davidson Breakout 114 is a striking and powerful cruiser designed for those who demand both style and performance. Powered by a 114ci Milwaukee-Eight® V-Twin engine, it delivers impressive torque and acceleration, ensuring a thrilling ride. The Breakout 114 features a muscular, chopper-inspired design with a wide, fat rear tire, long, sleek lines, and a minimalist profile that emphasizes its aggressive stance. Its advanced suspension and braking systems provide a smooth and controlled ride, while its refined aesthetics and premium finishes make it a standout choice for riders seeking a bold and high-performance cruiser.</p><p></p>
CYCLEMAX
Gaithersburg, MD
2016 Harley-Davidson 1200 Custom in Dumfries, VA
$7,950

Used 2016 Harley-Davidson Cruiser

1200 Custom
Stock # 443679
<p>There’s an all-new seat. A ground-devouring new suspension. Putting 1,200 cc of H-D® low-end torque to the pavement never felt better.</p><p style="margin-bottom: 1em;">Yeah, it’s got some bright work.</p><p style="margin-bottom: 1em;">Those who like it can rest assured, there is chrome in the Harley-Davidson® Sportster® arsenal. The Sportster® 1200 has plenty of shine to highlight its street brawling attitude. You’ve got 1200 cc of world famous H-D® low-end torque to motivate you down the asphalt. A comfortable new seat and a new suspension to make it all feel just right. And classic custom detailing. On any street in the word, this machine truly shines.</p><p></p>
Harley-Davidson of Quantico
Dumfries, VA
2019 Harley-Davidson Fat Boy® 114 114 in Fredericksburg, VA
$18,499

Used 2019 Harley-Davidson Cruiser

Fat Boy® 114 114
Stock # 019774
<p>SUPER CLEAN AND LOTS OF EXTRAS!!!! 2019 FAT BOY 114***MUSTANG 2 UP SEAT***V&H PIPES***PLUS MORE!! COME IN TODAY AND TEST RIDE IN FREDERICKSBURG VA</p><p style="margin-bottom: 1em;">Like New Low mileage Fatboy. Accessories include Grips, Mustache Engine Guard, Highway Pegs, Mustang 2 up Seat, Passenger Back Rest and Vance & Hines Mufflers that sound great paired with this 114 Engine!</p><p style="margin-bottom: 1em;">The original fat custom icon. Now lighter than the previous generation Fat Boy, and slinging torque from a Milwaukee-Eight® 114. You’ll feel the difference the instant you crack the throttle.</p><p></p>
Old Dominion Harley Davidson
Fredericksburg, VA
2016 Harley-Davidson 1200 Custom in Fredericksburg, VA
$6,495

Used 2016 Harley-Davidson Cruiser

1200 Custom
Stock # 12221
<p>There’s an all-new seat. A ground-devouring new suspension. Putting 1,200 cc of H-D® low-end torque to the pavement never felt better.</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 2016 Harley-Davidson Sportster 1200 Custom features a fuel injected 1200cc motor and 5 speed transmission. This Certified motorcycle received a new front tire as well as a full service at our dealership. </p><p style="margin-bottom: 1em;"><strong>Accessories Include:</strong></p><ul><li>ABS Brakes</li><li>Vance & Hines Mufflers</li><li>Upgraded Air Filter</li><li>Detachable Passenger Backrest / Luggage Rack</li><li>Custom Grips & Mirrors</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
2016 Harley-Davidson Softail Slim® SLIM in Duncansville, PA
$11,995

Used 2016 Harley-Davidson Cruiser

Softail Slim® SLIM
Stock # TTT024238
<p>The perfect blend of classic, raw bobber style and the power of a high output Twin Cam 103B™ engine. A modern ride with unmistakable old-iron attitude</p><p>The good old days are right now.</p><p>The Softail Slim® is study in contrasts. The Hollywood bars, slim rear wheel, cat eye console and floor boards recall the early days of custom motorcycle enthusiasm. Yet you also get thoroughly modern features like a High Output Twin Cam 103B™ engine, hidden suspension and great brakes to bring it all into the here and now. Notice the way bright chrome meets blacked-out metal. Laced wheels with stamped black rims. There’s never been a better time to be a rider.</p><p></p>
Roundhouse Harley-Davidson
Duncansville, PA
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