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Harley-Davidson SPORTSTER 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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87 Harley-Davidson Motorcycles For Sale

2022 Harley-Davidson® XL883N - Iron 883 IRON in Harrisonburg, VA
$8,999

Used 2022 Harley-Davidson® Cruiser

XL883N - Iron 883 IRON
Stock # 409866
2022 Harley-Davidson® XL883N - Iron 883 , 2022 Harley-Davidson® Iron 883™ <p>Blacked-out and stripped-down with a legendary profile.</p><p><strong>Features may include:</strong></p><strong>THIS IS THE RIGHT BIKE FOR</strong><ul><li>Urban riders seeking iconic style and V-Twin rumble</li></ul><ul><li>Middleweight power paired with precision handling</li></ul><ul><li>883cc Air-Cooled Evolution® V-Twin engine</li></ul><ul><li>883CC AIR-COOLED EVOLUTION® ENGINE</li></ul><p>Authentic Harley-Davidson style through and through. The rubber-mounted 883cc Evolution®?engine runs hard and rides smooth for thousands of miles so you can just ride.</p><ul><li>LOW SEAT HEIGHT</li></ul><p>The combination of a lowered front and rear suspension together with a low, narrow solo seat (just 25.7-inches high) provides comfort and confidence for riders of all sizes and experience.</p><ul><li>TUCK AND ROLL SEAT</li></ul><p>A solo seat that combines modern comfort with an authentic “tuck and roll” design inspired by the early days of the bobber.</p><ul><li>MACHINED 9-SPOKE WHEELS</li></ul><p>Blacked out nine-spoke wheels set off by a contemporary mechanical look machined into the spokes.</p><br><br>
Blue Ridge Powersports
Harrisonburg, VA
2017 Harley-Davidson SPORTSTER FORTY EIGHT FORTY EIGHT in Lower Burrell, PA
$7,000

Used 2017 Harley-Davidson Cruiser

SPORTSTER FORTY EIGHT FORTY EIGHT
<p>2017 Harley-Davidson Sportster 48, XL1200X up for sale. Approximately 2800 miles. Clean and garage kept. Clean title in hand. Asking $7,000 or best offer. Black on black with numerous modifications installed by Gatto HD in Tarentum. See modification list below. </p><p><br></p><p></p><p>Thanks!</p><p><br></p><p></p><p>Seat - Biltwell HB</p><p>Exhaust - Vance & Hines Short Shots</p><p>ECU - FP3 Fuelpak</p><p>Intake - Arlen Ness Big sucker</p><p>Rear Pegs - HD passenger pegs</p><p>Sissy bar - Burly style short bar</p><p>Tank lift/Ignition relocation - Kinetic cycles</p><p>Bars - Biltwell Frisco bars</p><p>Grips - Biltwell Thrusters</p><p>Derby cover - HD Motor Co.</p><p>Timing cover - HD Motor Co.</p><p>Headlight - Wisamic LED (Amazon)</p><p>Turn signals - Smoked (Amazon)</p>
Private Seller
Lower Burrell, PA
2009 Harley-Davidson SPORTSTER 883 LOW in Haymarket, VA
$2,999

Used 2009 Harley-Davidson Cruiser

SPORTSTER 883 LOW
Up for sale is my 2009 Harley Davidson XL883L Sportster. Bike has 23,xxx miles on it. Fuel injected, starts good and runs well. Vance and Hines Straightshots and a fuelpak so the bike sounds like a Harley should!Bike was serviced in March:2 new metzeler tires Oil changeBrand new batteryNew front brake rotorBike will also come with 3 keys. State inspection was just done!Clean title, and ready for a new home. Have my eyes on a new bike so looking to free up some space and cash.
Private Seller
Haymarket, VA
2016 Harley-Davidson SPORTSTER 1200 CUSTO R in Frederick, MD
$8,999

Used 2016 Harley-Davidson Cruiser

SPORTSTER 1200 CUSTO R
Stock # 438621
2016 HARLEY-DAVIDSON SPORTSTER 1200 CUSTO, <br/> <p>There&#8217s an all-new seat. A ground-devouring new suspension. Putting 1200cc of H-D® low-end torque to the pavement never felt better.</p> <ul class=primaryProductFeatures>;</ul> Overview <ul class=itemGroupFeatures><li id=40592662 class=productFeature>Yeah, it&#8217s got some bright work: 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&#8217ve 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.</li><li id=40592663 class=productFeature>Authentic Styling: When the first Sportster motorcycle roared onto the scene in 1957 the world had never seen anything like it. Rawboned, powerful and looking for action. The styling cues that lit up the street in those early years would soon become a part of everything from race bikes to outlaw choppers as they spread throughout the motorcycling world. Take a look at the offering for 2016 and one thing becomes instantly clear. The best way to get the style that made the Sportster motorcycle famous is to get a Sportster motorcycle of your own. The narrow frame is more agile than ever. The rumbling V-Twin and muscular front end feel more powerful than ever. The flawless steel and jewel-like fuel tank reveal their authentic American motorcycle roots in every inch of detail.</li><li id=40592664 class=productFeature>Iconic Engine: The Evolution engine riding in the nimble Sportster frame is a prime example of the power, durability and proven reliability The Motor Company was built on. Born from the legendary Shovelhead and Ironhead engines, it&#8217s been the power at the center of a Sportster motorcycle since 1984. Its overhead valve design and four-cam gear train have their roots in the company&#8217s race program, and you know it when you feel the surge of brute torque that accompanies every twist of the throttle. The air-cooled V-Twin design with a compact one-piece crankcase/transmission fits the narrow Sportster profile like a fist in a fingerless glove. We began with a strong, trouble-free design. Then gave it constant refinement to bring us to the modern powerplant of today. A testament to the unwavering hunger for advancement in motor technology that has always driven Harley-Davidson.</li><li id=40592665 class=productFeature>Technology: What the eye sees and the rider feels on a Sportster motorcycle go
JT Motorsports
Frederick, MD
2020 Harley-Davidson® XL883N - Sportster® Iron 883 IRON in Manassas, VA
$7,149

Used 2020 Harley-Davidson® Cruiser

XL883N - Sportster® Iron 883 IRON
Stock # U17664
2020 Harley-Davidson® XL883N - Sportster® Iron 883 , 2020 Harley-Davidson® Sportster® Iron 883™ <strong>EVERYTHING YOU NEED, NOTHING YOU DON’T</strong><p>An original icon of the Harley-Davidson® Dark Custom style. It sets the standard for the raw, stripped-down, blacked-out look.</p><strong>Features may include:</strong><ul><li>Blacked-Out Look</li></ul><p>It’s the poster bike of the anti-chrome movement. You’ve got a black powder-coated 883cc engine with black rocker covers. Black on the throwback round air cleaner cover. Chopped fenders, to show off a little rubber and black front forks with gaiters to add a little old-school nostalgia.</p><ul><li>Street Inspired Paint</li></ul><p>We created paint jobs with colors that look right against the backdrop of the urban grid, and don’t need a lot of maintenance. These are tough finishes, as mean as the meanest street.</p><ul><li>Low Seat & Slammed Suspension</li></ul><p>The combination of a lowered front and rear suspension together with a low, narrow solo seat—just 25.7-inches high—provides comfort and confidence for riders of all sizes and experience. The ride is responsive and plush, whether you're dodging urban potholes or out exploring the back roads.</p><ul><li>Tuck and Roll Seat</li></ul><p>A solo seat that combines modern comfort with an authentic “tuck and roll” design inspired by the early days of the bobber.</p><ul><li>Machined 9-Spoke Wheels</li></ul><p>Nine-spoke wheels that are black as night where the rim meets the rubber and set off by a more contemporary mechanical look machined into the spokes.</p><ul><li>883cc Air-Cooled Evolution® Engine </li></ul><p>Authentic Harley-Davidson style through and through, dripping with power. The rubber-mounted 883cc Evolution® engine runs hard and rides smooth for thousands of miles so you can just worry about taking in the freedom of boulevards and back streets.</p><ul><li>Drag-Style Handlebar</li></ul><p>Born at the drag strip, the low-rise, slammed black drag-style handlebar is an old-school garage feature that puts you in a forward, aggressive riding position.</p>
MotoMember of Manassas
Manassas, VA
2012 Harley-Davidson Sportster® Iron 883™ in Gaithersburg, MD
$5,995

Used 2012 Harley-Davidson Cruiser

Sportster® Iron 883™
Stock # HAR417443
<p>Sportster® Iron 883™</p><p style="margin-bottom: 1em;">Cyclemax has this Pre-Owned 2012 Harley-Davidson Sportster Iron 883 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 2012 Harley-Davidson® Sportster® Iron 883™ XL883N is an amazing way to get started with a custom motor bike. From the authentic Harley 883 cc engine to the chopped fenders to the peanut fuel tank, every piece of the Harley Sportster Iron 883 has the style you want in your custom motor bikes. For a combination of style and value look no further than the Harley-Davidson Iron 883. Also learn more about other Harley Sportster custom bikes such as the 1200 Low custom motorcycle and the Nightster® with a vintage motorcycle look. The other Sportster motorcycles all have their own personality. Learn more about each bike and its distinct style. For custom bikes and more the 2012 Harley motorcycles have it all.</p><p></p>
CYCLEMAX
Gaithersburg, MD
2009 Harley-Davidson SPORTSTER 1200 CUSTOM XL1200C in Mount Airy, MD
$6,500

Used 2009 Harley-Davidson Cruiser

SPORTSTER 1200 CUSTOM XL1200C
<p>2009 Harley Davidson Sportster XLC - 6950 miles</p><p>Garage kept  - lightly ridden</p><p><br></p><p>Includes: </p><p>Battery Tender - Charger</p><p>Harley Reach seat and full seat included, easy to swap</p><p>Wind Splitter Quick-Release Compact 18 in. Windshield</p><p>Harbor Freight - PITTSBURGH MOTORCYCLE 1800 Lb. Capacity Motorcycle Stand/Wheel Chock - Item 61670 / 97841</p><p>Helmets: Men’s Harley 1/2 helmet - medium - black</p><p>Women’s Harley Full Helmet - small - black</p><p>Men’s Full Helmet - HJC - gray</p><p><br></p><p>Service Work:</p><p>new battery - year old</p><p>oil changed year ago</p><p>Few small rust spots on chain guard, otherwise in good shape, never dropped</p><p>All service work performed by Li’l Hops in Eldersburg, MD</p><p><br></p><p>Harbor Freight - PITTSBURGH MOTORCYCLE 1800 Lb. Capacity Motorcycle Stand/Wheel Chock - Item 61670 / 97841</p><p>Helmets: Men’s Harley 1/2 helmet - black</p><p>Women’s Harley Full Helmet</p><p>Men’s Full Helmet </p><p><br></p>
Private Seller
Mount Airy, 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
2017 Harley-Davidson Iron 883™ IRON in Orange, VA
$8,995

Used 2017 Harley-Davidson Cruiser

Iron 883™ IRON
Stock # 445702
<p>Aggressive throwback styling taken to a place altogether new. No need to shine this machine. Just get on and tear up the nearest street.</p><p style="margin-bottom: 1em;">A great leap forward in the dark arts.</p><p style="margin-bottom: 1em;">You’re looking at a pioneer of raw, blacked-out, stripped-down custom style. In the years since its introduction, it has only gotten better. Fine-tuned suspension. Tuck and roll seat. Black cast aluminum wheels with machined highlights. And blacked-out surfaces from fender to fender. You get everything you need. And nothing you don’t.</p><p></p>
Stonewall Harley-Davidson
Orange, VA
2018 Harley-Davidson Iron 883™ IRON in Fredericksburg, VA
$5,995

Used 2018 Harley-Davidson Cruiser

Iron 883™ IRON
Stock # 10902
<p>RAW, BLACKED-OUT, STRIPPED-DOWN CUSTOM STYLE</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 2018 Harley-Davidson Sportster Iron 883 features a fuel injected 883cc motor and 5 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>Custom Paint Set</li><li>LED Headlight</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 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
2015 Harley-Davidson Iron 883™ IRON in Fredericksburg, VA
$5,495

Used 2015 Harley-Davidson Cruiser

Iron 883™ IRON
Stock # 11491
<p>Iron 883™</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 Sportster Iron 883 features a fuel injected 883cc motor and 5 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>Custom Paint Set</li><li>LED Headlight</li><li>Custom Intake</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 Sportster 1200 Custom in Fredericksburg, VA
$4,695

Used 2009 Harley-Davidson Cruiser

Sportster 1200 Custom
Stock # 11633
<p>Sportster® 1200 Custom</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 Sportster Custom features a fuel injected 1200cc motor and 5 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>Vance & Hines Mufflers</li><li>Upgraded Air Filter</li><li>Mustang Seat</li><li>Mini Rider Footboards</li><li>Custom Grips</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 Sportster® 883 Low SUPERLOW in Fredericksburg, VA
$4,295

Used 2009 Harley-Davidson Cruiser

Sportster® 883 Low SUPERLOW
Stock # 11828
<p>Sportster® 883 Low</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 Sportster 883 Low features a fuel injected 883cc motor and 5 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>Custom Paint Set</li><li>Headlight Cowl</li><li>Slash Cut Mufflers</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
2009 Harley-Davidson Sportster® 883 Low SUPERLOW in Fredericksburg, VA
$11,995

Used 2009 Harley-Davidson Cruiser

Sportster® 883 Low SUPERLOW
Stock # 12109
<p>Sportster® 883 Low</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 Sportster 883 Low features a fuel injected 883cc 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>Frankenstein Trike Kit - $7500+ Value</li><li>Cobra Exhaust</li><li>Engine Guard</li><li>Mustang Solo Seat</li><li>Mini Rider Footboards</li><li>LED Headlight, Taillight, & Turn Signals</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
2017 Harley-Davidson Iron 883™ IRON in Duncansville, PA
$6,995

Used 2017 Harley-Davidson Cruiser

Iron 883™ IRON
Stock # T434066
<p>Aggressive throwback styling taken to a place altogether new. No need to shine this machine. Just get on and tear up the nearest street.</p><p>A great leap forward in the dark arts.</p><p>You’re looking at a pioneer of raw, blacked-out, stripped-down custom style. In the years since its introduction, it has only gotten better. Fine-tuned suspension. Tuck and roll seat. Black cast aluminum wheels with machined highlights. And blacked-out surfaces from fender to fender. You get everything you need. And nothing you don’t.</p><p></p>
Roundhouse Harley-Davidson
Duncansville, PA
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